Amtrak Guide

By train travelers for train travelers, 20 best amtrak trips from chicago.

California Zephyr in Dotsero, Colorado

Chicago is one of the best cities for train travel. Sixteen Amtrak routes arrive and depart from Chicago Union Station , so there are many options for day, weekend or multiple-day getaways. Here are some of the best trip options listed in order of travel time so you can start planning your rail adventure. Destinations were selected based on convenient train departure times and unique things to see and do.

This website is reader supported and not affiliated with Amtrak. We may earn a small commission from links on this page . For current schedules, visit,

Miller Brewing Company

For a day or overnight trip, travel to Milwaukee on the Hiawatha Amtrak route. Travel time is about 1.5 hours, and you’ll arrive near the Historic Third Ward neighborhood and the RiverWalk. There are several museums and a zoo to explore, including the Harley-Davidson Museum, which is in walking distance of the Amtrak station. You can also go to a sporting event, visit the many breweries or attend one of the city’s many festivals .

St. Joseph/Benton Harbor

Benton Harbor Lighthouse

Escape the city and experience Lake Michigan from the charming towns of St. Joseph and Benton Harbor via the Pere Marquettte Amtrak route. In addition to beaches and parks, explore the Sarett Nature Center , Silver Beach Carousel and wineries. This trip from Chicago is only two hours, but you’ll need to stay at least one night in Michigan as there is only one train each day.


Abraham Lincoln Presidential Museum

Book a trip on the Texas Eagle or Lincoln Service to visit Springfield , the Illinois capital. Major attractions here include the Abraham Lincoln Presidential Library and Museum , Lincoln Home National Historic Site, Illinois State Museum and various other historic homes and parks. If you plan to do a day trip, you’ll have about six hours to explore if you choose the morning departure from Chicago and evening departure from Springfield.

Wisconsin Dells

Dells of the Wisconsin River from High Rock

A great destination for kids, the Wisconsin Dells is full of water parks , theme parks, wildlife parks and outdoor activities . It’s approximately a four-hour train ride from Chicago on the Empire Builder , with an arrival around dinnertime. Plan to stay two nights in order to have a full day to visit the local attractions. You can walk to several hotels and motels near the Amtrak station ( White Rose Inn s and Alpine Motel are two of the top-rated places to stay) or check out hotels with shuttles (verify service with the hotels before booking).

chicago day trips by train

About 5.5 hours away from Chicago by train, St. Louis is known for the Gateway Arch , but there are many other things to see and do. Some of the top attractions include the Missouri Botanical Garden, St. Louis Zoo, St. Louis Art Museum, Mississippi River and Busch Stadium. There are multiple trains to choose from each day, so a day trip is doable, but due to the longer travel time, you may want to stay overnight in St. Louis .

Minneapolis/St. Paul

Lake Calhoun in Minneapolis

Minneapolis and St. Paul are full of cultural attractions, sport venues and outdoor activities — including a  scenic bike trail  along the Mississippi River,  Chain of Lakes recreation  and a beautiful  urban park with a waterfall . If you don’t like cold weather, plan to visit between May and September, although the  Saint Paul Winter Carnival  is a historic event worth checking out. Travel time from Chicago is almost eight hours.

Niagara Falls

chicago day trips by train

Visit the majestic Niagara Falls with a getaway on Amtrak’s Lake Shore Limited route. This is an overnight trip with a morning arrival in Buffalo, New York. Roomettes and bedrooms are available for a more comfortable and private experience on the train. Travel time is 10 hours, and you’ll be sleeping most of that time.

On the return trip to Chicago, the Lake Shore Limited departs Buffalo around midnight, which means you can spend the day sightseeing and get back on the train same day instead of staying at a hotel.

You’ll need to rent a car or use a taxi or rideshare service to reach downtown Buffalo and the Niagara Falls area — both have hotels if you plan to stay overnight. An Enterprise rental car office is near the Amtrak station. Call ahead to confirm pickup from the Amtrak station. The falls are about a 40-minute drive away from the train station and 30 minutes from Enterprise. FlixBus also departs from downtown Buffalo and travels to the Niagara Falls State Park .

Beale Street in Memphis

About 10.5 hours away from Chicago, Memphis is full of music and iconic places. It’s a party every night on Beale Street , and during the day you can visit Graceland, Sun Studio, the National Civil Rights Center and other tourist sites . When you aren’t sightseeing, eat the city’s famous barbecue or go on a top-rated food tour .

The Greenbrier Resort

chicago day trips by train

Travel through the beautiful New River Gorge on the Cardinal route to reach The Greenbrier , a 1778 resort with casino. The Cardinal only operates three days each week, so you will need to stay more than one night, but there are plenty of activities to keep you busy. In addition to the casino, there is a spa, golf course, swimming pools, bike rentals, bowling alley, fishing, aerial adventure course and more. Travel time is about 17 hours from Chicago, and the White Sulphur Springs Amtrak Station is conveniently next to the resort, so you don’t have to rent a car.

Washington D.C.

Washington Monument in DC

Washington D.C. is about 17 hours away from Chicago via the Capitol Limited route. The train departs Chicago around dinnertime and arrives at D.C. Union Station in early afternoon. At the station you can transfer to WMATA subway trains for easy access to museums , monuments and hotels. Taxi and rideshare cars are also options for getting around. Plan to stay in Washington D.C. at least one night before returning to Chicago. View top-rated hotels to find a place to stay.

New York City


Be a part of the city that never sleeps with trip to New York City . Travel time is between 19 and 20 hours on the Lake Shore Limited Amtrak route, with an arrival at the new Penn Station train hall in the evening. Penn Station has connections to the MTA subway and you can easily walk to the Empire State Building and Times Square . If you plan to see a Broadway Show, you’ll need to stay two nights in the city and use your first night to get settled at your hotel and see any attractions that aren’t at a scheduled time (in case there are train delays).

New Orleans

chicago day trips by train

Plan a trip to New Orleans for amazing food, music and culture. The City of New Orleans train departs Chicago in the evening and arrives 20 hours later in the afternoon. The return train departs each day in the afternoon, so you could stay one night in New Orleans and have time to see some of the sights. Attractions to check out include the National World War II Museum , Garden District, French Quarter and historic cemeteries. There are also boat tours and streetcars for sightseeing.

Boston in Autumn

Eat lobster, drink local craft beer and relive American Revolution history in Boston . The Freedom Trail is a must-do. Travel time is 21-22 hours to and from Boston’s South Station on the Lake Shore Limited route, with an evening departure from Chicago and evening arrival in Boston. You can also book your Amtrak ticket to the Back Bay Station, which is closer to Fenway Park and Copley Place shopping mall.

September and October are great months to visit, along with the summer months. Plan to stay two nights in the city, otherwise, you’ll basically only have one morning to see the sights before the daily early afternoon train back to Chicago.

Rocky Mountains

California Zephyr in Glenwood Canyon

The California Zephyr is arguably the most scenic Amtrak route, especially the journey through the Rocky Mountains along the Colorado River (pictured above). There are multiple Amtrak stations in the Rockies with lodging and activities so you can enjoy time there before returning to Chicago.

If you love skiing, book your Amtrak ticket to Fraser/Winter Park (21-hour trip) and hit the slopes at the popular Winter Park Resort . Glenwood Springs (25 hours from Chicago and pictured top of page), is another great option with hotels and a hot springs pool in walking distance of the Amtrak station. There are also hiking trails, whitewater rafting, an amusement park and the Frontier Historical Museum to explore.

chicago day trips by train

When the weather gets cold in Chicago, head to Texas on the Texas Eagle to explore Dallas or Austin . Dallas is 22 hours away from Chicago by train and Austin is 28. Both have surprisingly walkable areas near the Amtrak stations, light rail transit and rental car options.

In Dallas, the John F. Kennedy Memorial Plaza , the site of his assassination and the Sixth Floor Museum are all in walking distance of the Dallas Amtrak Station . There are also many other museums and an aquarium nearby, or rent a car to reach the George W. Bush Presidential Library and the Dallas Arboretum and Botanical Garden.

For a vacation full of music, nightlife and outdoor recreation, travel to Austin. There are many parks along the Colorado River to explore, boat rentals and tours, kayaking, paddleboarding, festivals, and live entertainment on 6th Street .


Albuquerque Balloon Fiesta

Albuquerque is 26 hours away from Chicago on the Southwest Chief . It’s New Mexico’s largest city, plus you’ll travel through mountains on the way there. Top attractions include Sandia Peak Tramway for gorgeous panoramic views, Indian Pueblo Cultural Center , National Museum of Nuclear Science and the Petroglyph National Monument . There’s also plenty of things to check out near the Amtrak station, including a zoo , botanic garden , Old Town Albuquerque , and trails along the Rio Grande River. Consider planning your trip around the Albuquerque International Balloon Fiesta , which is a major event in the fall.

Glacier National Park

chicago day trips by train

Take Amtrak to Glacier National Park on the Empire Builder to see stunning landscapes and relax in a historic inn. There are four train stations near the park to choose from, each with unique lodging options. East Glacier Park is the first stop, about 30 hours away from Chicago, and you can walk to the Glacier Park Lodge from the station. Next is Essex Station, which is next to the historic Izaak Walton Inn . West Glacier Station is the third station near the park, with the West Glacier Village, the 1910 Belton Chalet and other lodges in walking distance. Or get off the train in Whitefish if you want to rent a car or stay in an area near restaurants.

Los Angeles

Hollywood Sign Los Angeles

Travel to Los Angeles for a 43-hour, two-night trip on the entire length of the Southwest Chief Amtrak route. You’ll travel though mountains and deserts and arrive at the beautiful Los Angeles Union Station in the morning. There’s plenty to see and do in the city, including the Getty Center , Griffith Observatory , Hollywood Sign , Santa Monica Pier , theme parks, tours, shopping and beaches. If you don’t want to take Amtrak back to Chicago, there are plenty of direct flights to choose from.

Portland and Seattle

Portland Oregon Skyline

Last, but not least, is the full long-distance trip on the Empire Builder . You have the choice to travel from Chicago to either Portland or Seattle . Both options offer amazing scenery, with views of the Columbia River Gorge on the Portland route, or travel along Puget Sound and multiple rivers on the Seattle segment. You’ll also see the Rocky Mountains in Montana if you book your trip around the summer solstice. Total travel time is 46 hours, with two nights on the train. You can easily get a flight back to Chicago in Portland or Seattle to shorten the return trip.

More Information

  • Amtrak’s 15 Long-Distance Routes
  • 7 Essential Things to Pack for an Amtrak Trip
  • Popular Amtrak destinations from Chicago

Top photo credit: Loco Steve/ (California Zephyr train in Colorado)

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5 Best Day Trips From Chicago By Train

Last Updated By VacationIdea on April 11, 2024 in Illinois

Day Trips From Chicago By Train

From Chicago to Milwaukee

From Chicago to Milwaukee

Popular things to do in Milwaukee include visiting the Art Museum and the Harley-Davidson Museum . A trip to the Mitchell Park Horticultural Conservatory is always worth one's time as well, and a walk along the side of the Menomonee River is particularly enjoyable for families and couples alike. More Day Trips from Chicago

From Chicago to Oak Park

From Chicago to Oak Park

Best known as the home of famed architect Frank Lloyd Wright, Oak Park is a really pretty place with a lot to offer. You can enjoy a full Frank Lloyd Wright tour, visiting the architect's former home and studio, as well as passing by some of the beautiful houses he helped create. There are some quality craft beer bars and decent restaurants to be found in Oak Park as well, so it's great for a relaxing day out. More ideas: Weekend Getaways from Chicago

Day Trip to Michigan City from Chicago

Day Trip to Michigan City from Chicago

Once you arrive at Michigan City, you can explore and experience some of the various attractions like Washington Park Zoo, the Old Lighthouse Museum, and the always-impressive Barker Mansion. Otherwise, if you're just in the city to lie back and relax, you can head down to the beach and admire the amazing views all around you. More ideas: Romantic Getaways in Illinois

Kalamazoo from Chicago

Kalamazoo from Chicago

More ideas: Best Day Trips in Illinois , Ski Resorts Near Chicago

Day Trip to Libertyville from Chicago

Day Trip to Libertyville from Chicago

You won't find too many major attractions or monuments in Libertyville, but it's a lovely location for those who just want a calm and pleasant day out of the city. There are some super bars and restaurants here, as well as a great range of boutiques and small stores. The local movie theater is quite a popular hangout spot too. More ideas: Places to Visit in Illinois

  • 1. From Chicago to Milwaukee
  • 2. From Chicago to Oak Park
  • 3. Day Trip to Michigan City from Chicago
  • 4. Kalamazoo from Chicago
  • 5. Day Trip to Libertyville from Chicago

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BEST Day Trips From Chicago (By Car, Bus & Train)

Looking to leave Chicago for the day or even a few hours? Fortunately there are many amazing places to visit in the Midwest near the city whether you love nature, beaches, cities or small towns. Here are the best day trips from Chicago all less than 2 hours from the city.

If you don’t have a car or would rather not drive, you can also visit most of these places by train, bus or through a guided day tour.

Best Day Trips From Chicago

Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you.

Starved Rock State Park

Distance from Chicago: 95 miles Time from Chicago: 1 hour and 40 minutes Address: 2668 East 873 Road, Oglesby, Illinois

Starved Rock State Park is one of the best day trips from Chicago

Starved Rock State Park is one of the top attractions in the state of Illinois. The park is an ideal spot to enjoy nature and is filled with stunning sandstone canyons and beautiful waterfalls. This is a great place for hiking with 13 miles (21 kilometers) of trails.

In addition to hiking, visitors can enjoy outdoor activities year round, including horseback riding, ice climbing, cross-country skiing, as well as fishing, kayaking, rafting on the Illinois River.

Matthiessen State Park

Distance from Chicago: 96 miles Time from Chicago: 1 hour and 40 minutes Address: 2500 IL-178, Oglesby, Illinois

Matthiessen State Park is not as popular or crowded as nearby Starved Rock State Park (less than 3 miles away) but it is just as beautiful with similar natural features such as canyons and beautiful waterfalls.

Oak Park, Illinois

Distance from Chicago: 10 miles Time from Chicago: 15-20 minutes from downtown

Oak Park is a suburb on the outskirts of Chicago. The village prides itself on its racial, ethnic, socio-economic, and religious diversity . Downtown Oak Park is home to a variety of shops and restaurants but the main draw for visitors is the architecture.

Oak Park is home to the world’s largest collection of designed sites by Frank Lloyd Wright, the famous architect. Take a walking tour of the Wright District, an area of prairie-style homes designed by Frank Lloyd Wright including the Frank Lloyd Wright Home and Studio, and Unity Temple, a Wright–designed church considered to be one of his most important structures.

For those who would rather not drive, Oak Park is easily accessible from Chicago by train (Green Line and Blue Line on the CTA and Union Pacific / West Line on the Metra ). Ridesharing services such as Uber and Lyft are also an option.

Evanston, Illinois

Distance from Chicago: 14 miles Time from Chicago: 30 minutes from downtown Chicago

Looking for an easy day trip from Chicago? Visit Evanston, a nearby suburb located on the shores of Lake Michigan. Visit and relax at the beautiful Northwestern Campus. Evanston is home to six public swimming beaches which are less crowded than Chicago beaches.

If you have more time, you can explore more of the North Shore suburbs . Must see attractions in the North Shore include the Chicago Botanic Gardens in Glencoe, the Bahá’í Temple in Wilmette and the Kohl Children’s Museum in Glenview.

For those who would rather not drive, Evanston is easily accessible from Chicago by train (Purple Line) on the CTA and the Union Pacific North Line (UP-N) on the Metra . Ridesharing services such as Uber and Lyft are also an option.

Illinois Beach State Park

Distance from Chicago: 45 miles Time from Chicago: 1-1.5 hours drive

Illinois Beach State Park , part of the Illinois state park system, is located along Lake Michigan in northeast Illinois. It is known primarily for the beach with over six miles of shoreline. The park also includes dune areas, wetlands, prairie, and black oak savanna. Activities at the park include boating, swimming, fishing, hiking, camping, and more.

Cheap Car Rentals

Indiana Dunes, Indiana

Distance from Chicago: 50 miles Time from Chicago: 1 hour

The Indiana Dunes National Park borders the State Park of the same name. The national park offers 15 miles of shoreline along Lake Michigan’s southern shore with wide sandy beaches and towering dunes. Hikers will enjoy 50 miles of trails over rugged dunes, mysterious wetlands, sunny prairies, meandering rivers and peaceful forests.

The three highest sand dunes are all in the Indiana Dunes State Park.

In addition to beaches and hiking, Indiana Dunes offers many outdoor year round activities including bird watching, fishing, cycling, horseback riding, kayaking and paddling, snowshoeing, and cross country skiing.

New Buffalo, Michigan

Distance from Chicago: 70 miles Time from Chicago: 1 hour 15 minutes

New Buffalo, Michigan is a charming beach town on the shores of Lake Michigan. The beaches face west and have beautiful sunset views.

In addition to the beaches, a must see attraction is Galien River County Park , a beautiful park with boardwalk paths through the marsh.  For those that enjoy gambling, New Buffalo is home to the Four Winds Casino Resort .

New Buffalo has daily Amtrak service from Chicago on the Blue Water and Wolverine lines.

New Buffalo is a good base to explore various beach towns and wineries in Southwest Michigan .

Rockford, Illinois

Distance from Chicago: 85 miles Time from Chicago: 1.5-2 hours

Anderson Japanese Gardens in Rockford Illinois is one of the best day trips from Chicago

The most popular attraction in Rockford is Anderson Japanese Gardens , a 12-acre Japanese garden. If you have more time in Rockford before heading home, the city plenty of attractions including the Discovery Center Museum (a great family museum), Nicholas Conservatory and Gardens, Burpee Museum of Natural History, Tinker Swiss Cottage Museum and the Rockford Art Museum.

Lake Geneva, Wisconsin

Distance from Chicago: 83 miles Time from Chicago: 1 hour 40 minutes

Lake Geneva Wisconsin day trips from Chicago

In the summer, daytrippers can enjoy a variety of activities on the water, including boating, kayaking, paddle boarding. In the winter, visitors can go skiing or snowboarding or visit the beautiful ice castles.

The highlight is the Lake Geneva Shore Path, a 21-mile trail around the lake with stunning views of the forest, water and impressive waterfront homes. Visitors can hike or take a cruise around the lake.

Read about more things to do in Lake Geneva here .

Milwaukee, Wisconsin

Distance from Chicago: 93 miles Time from Chicago: 1 hour 40 minutes

This lively city is like a smaller less touristy version of Chicago.

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Amtrak Hiawatha train offers frequent daily service between Milwaukee and Chicago.

Tubing on the Tippecanoe River

Distance from Chicago: 105 miles Time from Chicago: 2 hours

Tippecanoe River State Park in northern Indiana is a popular Midwest summer destination. In the summer, you can rent tubes and float along the lazy river or you can also rent canoes or kayaks from various outfitters.

South Bend, Indiana

Distance from Chicago: 97 miles Time from Chicago: 1.5 to 2 hours

South Bend is most famous for being home to the University of Notre Dame. There are many attractions on the beautiful, large campus including the Golden Dome, Notre Dame Stadium, the Basilica of the Sacred Heart and the Grotto of Our Lady of Lourdes, a replica of the famous shrine.

One of the best things to see in South Bend is the Studebaker National Museum , featuring a large collection of Studebaker automobiles drawn from the history of the company, beginning with horse-drawn carriages. They also have the carriage that Abraham Lincoln took to Ford’s Theater the night he was assassinated.

In addition to driving, South Shore Line commuter rail runs multiple daily trains between Millennium Station in downtown Chicago and South Bend Airport station.

Pontiac, Illinois (Historic Route 66)

Illinois historic route 66 sign

Distance from Chicago: 100 miles

Historic Route 66 is a classic American road trip . Don’t have time to drive Route 66 all the way from Chicago to California? You can visit Pontiac and drive a portion of historic Route 66 on a day trip from Chicago.  Must see attractions in Pontiac include the IL Route 66 Association Hall of Fame & Museum , the Pontiac-Oakland Automobile Museum and the Route 66 Shield Mural .

What are your favorite day trips from Chicago ?

Planning a trip to Chicago? Check out my Chicago guides and itineraries:

  • 3 Days in Chicago Itinerary + Travel Tips From a Local
  • The Perfect Itinerary for One Day in Chicago (According to a Local)
  • Most Instagrammable Places in Chicago
  • Best Free Things to Do in Chicago

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9 Spectacular Must-Do Day Trips From Chicago (2024 Guide)

Alesha and Jarryd

  • Last Updated: February 4, 2024

Looking for a good day trip from the Windy City? Here are 9 amazing day trips from Chicago that include state parks, beaches, historic sites and more.

Chicago is a city of mouthwateringly good deep-dish pizza, pristine architecture, and an enriching atmosphere. Full of top-notch restaurants, eye-catching fashion, and upscale attractions, the Windy City is a place people travel from all over to visit.

A place of innovation, Chicago is constantly up to speed with new trends – or establishing the trends for everyone to catch onto.

Of course, as the birthplace of modern architecture, this is not a big surprise. Still, a visit here catches one’s eye with the fascinating designs and structures of the buildings within the third largest city in the United States. 

While visiting this trendy city, we recommend spending a day outside Chicago to see nearby top attractions like state parks full of hiking trails. There is so much to see outside the town center of Chicago, so why not add a day trip or two to your Chicago itinerary ?

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars , which has the largest range of vehicles for the best value on the market.

Table of Contents

What Is There To See And Do?

Getting there and away, best time of year to visit, the 9 best day trips from chicago.

It’s time to spread your wings and leave the city on an incredible day trip. Take your pick from our curated selection of the 9 best day trips from Chicago. From living in luxury in Lake Geneva to exploring the rich history and architecture of Oak Park, get ready to have the time of your life.

Find more of the best things to do in Chicago here !

1. Starved Rock State Park

  • Distance from Chicago: 91 miles/146 km
  • How Long it Takes: 1½ Hours

Settled along the Illinois River, Starved Rock State Park is an oasis teeming with seasonal waterfalls, towering sandstone canyons, thriving wildlife, and scenic hiking trails.

However, the most well-known landmark at the park is the cliff the park is named after – Starved Rock. This imposing sandstone cliff is a natural landmark that holds history. 

Archaeological excavations have been run at Starved Rock for further research to verify information shared throughout history. In 1683, the French used Starved Rock to establish a fort called Fort St. Louis. It was later abandoned in 1691. 

The sandstone cliffs were named “Starved Rock” by Native Americans in 1770 after what is estimated to be about 2,000 Native Americans died atop the cliffs. This was after the Potawatomi Indians attacked the Peoria Indians.

As a result, the Peoria Indians were trapped on the rock and suffered starvation. 

Today, Starved Rock State Park has become a favored spot to sink into nature’s beauty. People come from all over to see Starved Rock and other popular landmarks, including the St. Louis Canyon Falls.

The St. Louis Canyon Falls towers an impressive 80 feet, one of the highest waterfalls in Illinois. In summer and spring, visiting these falls is one of the top activities to do at the park. You can also go kayaking , canoeing, or try other water sports.

Top attractions in the park include:

  • St. Louis Canyon Falls
  • Aurora Canyon
  • Illinois Canyon
  • Starved Rock State Park Lodge 

Popular hiking trails:

  • St. Louis Canyon Trail
  • River Trail
  • Bluff Trail
  • French Canyon Trail

There are two popular methods of getting to Starved Rock State Park from Chicago without a car. The first is taking the train from Chicago Union Station to Mendota Amtrak Station. The second would be to take a taxi, which can be much more expensive but is a quicker route.

We recommend visiting from April to September as it’s ideal weather for outdoor activities. If you’re an avid birdwatcher, then the best time of year to visit Starved Rock State Park to see the eagles is in January and February. 

The spring is the best time to see the waterfalls as they are seasonal and fed by heavy rains often experienced during the spring.

The summer is the most popular time to visit Starved Rock State Park. Unfortunately, this is when the park can get overcrowded, resulting in the park cutting off entry for visitors, as many people come to kayak and raft on the river. 

Starved Rock State Park

2. Lake Geneva

  • Distance from Chicago: 83 miles/134 km
  • How Long it Takes: 1 Hour 45 Minutes

A resort city, Lake Geneva, was named “Newport of the West” after the American Civil War. The year-round resort city was where rich Chicago residents constructed their summer homes. Some famous names that visited the area include General Sherman and Mary Todd Lincoln. 

This area has a rich history, where ancient Oneota Tribes of the lost Hopewell Culture Indians once thrived. Archaeological evidence suggests that the Oneota Tribes had an advanced civilization here in 1,000 BC.   

Today, Lake Geneva is one of the best weekend getaways from Chicago. A day trip or weekend trip here is worth taking because of its natural beauty, impressive architecture, and luxurious resorts.

Take your pick of boating on the lake, hot air ballooning over the resort city, joining a history tour, or sinking into luxury with a spa day at The Abbey Resort.

Examples of popular things to see include:

  • Riviera Beach
  • Big Foot Beach State Park 
  • Lake Geneva Shore Path
  • Royal Oak Farm 
  • Safari Lake Geneva

There are no trains directly connecting Chicago to Lake Geneva. Another option would be to take the train from Chicago Union Station to Fox Lake. From there, snag a taxi to this Wisconsin resort city. 

To catch some sun outdoors by the lake, the best time to visit Lake Geneva is in the summer. This is the optimal time for weekend getaways or day trips from Chicago. The days get hot, so wear sunscreen and bring plenty of water to stay hydrated.

Have 3 days to spare in Chicago? Check out our ultimate 3-day itinerary ! 

3. Indiana Dunes National Park

  • Distance from Chicago: 39 miles/62 km
  • How Long it Takes: 1 Hour

One of the best day trips from Chicago, Indiana Dunes National Park is thriving with natural wonders with over 50 miles of scenic trails to observe these eye-catching features. A road trip through here is sure to be a beautiful one!

The park has one of the most biologically diverse habitats in the United States, including wetlands, shorelines, prairies, and sand dunes. This includes the 15 miles of Indiana Dunes National Park beaches stretching down Lake Michigan’s southern tip. 

Though the beach is one of the top things to do when visiting Indiana Dunes National Park, the park is also notorious for its rich history.

The Bailly Homestead, a National Historic Landmark, was the home of one of the first settlers in the area, Joseph Bailly de Messein. This fur trader’s trading post acted as an in-between for travelers from Detroit to Chicago. 

Top attractions in the park:

  • Chellberg Farm
  • Bailly Homestead
  • Kemil & Dunbar Beaches
  • Paul H. Douglas Trail 
  • Great Marsh Trail
  • Cowles Bog Trail
  • Dunes Succession Trail (Diana of the Dunes Dare)

The best way to get to Indiana Dunes National Park is by renting a car. Unfortunately, there are no methods of transport that take you directly to the park. You can take a taxi, but it will be quite expensive!

Summer is the best time of year to visit Indiana Dunes National Park. This is when the beaches are open and prime for sunbathing and swimming. Other activities like fishing and hiking to see the sand dunes are also great at this time. 

Indiana Dunes National Park

4. Silver Beach County Park

  • Distance from Chicago: 98 miles/157 km 
  • How Long it Takes: 1 Hour 45 Minutes 

Bordering four states, Lake Michigan seeps into Illinois, Indiana, Michigan, and Wisconsin. Though Lake Michigan is technically within access of Chicago, with popular attractions like the Navy Pier and Millenium Park, one of the top day trips from Chicago is Silver Beach County Park.

Located at the mouth of the St. Joseph River on Lake Michigan’s southern shore, Silver Beach County Park has lots of picturesque viewpoints.

The long, clean stretch of beach has become a top tourist destination with upgraded renovations made to the park to promote accessibility and convenience. 

Access to Silver Beach County Park is free, though parking can be tricky depending on how busy it is. The barrier-free walkway gives easy access to the South Pier, Dunes Pavilion, concession stand, Shadowland Pavilion, and restrooms.

Using the park’s sidewalks along the beach, you can reach the Silver Beach Center, find the Whirlpool Compass Fountain, and take a refreshing stroll to downtown St. Joseph.

Cool things to see in the area:

  • Silver Beach Carousel
  • Krasl Art Center
  • Harbor Shores Golf Club
  • Whirlpool Compass Fountain

There are several ways to get to Silver Beach County Park from Chicago without a car. The first is a train ride from the Chicago Union Station to St. Joseph-Benton Harbor, Michigan.

The second is a bus ride from the Chicago Bus Station to Benton Harbor and a taxi to Silver Beach County Park. The third would be getting a taxi or renting a car to reach Silver Beach County Park. 

Silver Beach County Park is open daily from dusk to dawn. For swimming, the best time of year to visit is usually anywhere from July to September. Lifeguards are on duty at the park from June to August. 

Exploring more of the Midwest? Check out our list of the best things to do in Minneapolis, Minnesota !

5. Anderson Japanese Gardens

  • Distance from Chicago: 85 miles/137 km

One of the highest-quality Japanese gardens in the United States, the Anderson Japanese Gardens is among the most rewarding Chicago day trips.

The authentic Japanese garden inspires by its refined outdoor setting that has been maintained and designed with the highest standards.

The Anderson Japanese Gardens were designed by Hoichi Kurisu, who established many other Japanese gardens, including the one at the Samaritan Lebanon Community Hospital that won the Healthcare Environment Award in 2006 for Landscape Design. 

Exuding eloquence and grace, this location soothes the soul as guests stroll through the thriving landscapes.

Yoga sessions are taught within the gardens in the Hatha Yoga tradition amongst the refreshing air of the gardens. There are beginner, intermediate, and advanced classes for Tai Chi led at the gardens to encourage relaxation and mental focus. 

Fun things to do here include:

  • Amanda Stivers yoga
  • Sound & gong bath
  • Awareness walks

Other fun things to do in the area include:

  • Rockford Art Museum
  • Laurent House
  • Prairie Street Brewing Company
  • Nicholas Conservatory & Gardens
  • Burpee Museum of Natural History
  • Discovery Center Museum

Take the bus from the Chicago Union Station to Rockford Amtrak Station. From there, hitch a ride on a taxi.

Another option is to take the subway Jackson-Blue to O’hare in Bensenville. Once you reach the station, hitch a bus ride from the Chicago – O’hare Airport to the Rockford Bus Terminal. Then, grab a taxi to reach the gardens.

Taking a car is the second best option for a more cost-effective option, but it is more convenient than taking the bus and taxi to reach Anderson Japanese Gardens.

The best time to witness the stunning transition of the leaves as they turn color at Anderson Japanese Gardens is in Fall, from September to October. However, summer is the peak season, so if you want to avoid the crowds stick to visiting in the spring or fall. 

Anderson Japanese Gardens

6. Oak Park

  • Distance from Chicago: 10 miles/15 km
  • How Long it Takes: 20 Minutes

Within a short distance from Chicago, Oak Park is a historically rich village place to visit. It is also considered one of the best places to live in Illinois, intertwining suburban and urban living in one favorable family-friendly location. 

There are plenty of activities in the area, with family-friendly attractions like the Brookfield Zoo and the Galloping Ghost Arcade. The arcade is the largest video arcade in the United States. Oak Park is notorious for its trendy restaurants like Maya Del Sol or Hemmingway’s Bistro. 

If you’re a history buff or appreciate architecture, you’ll love this beautiful spot. Renowned architect Frank Lloyd Wright showcased his talent here for the first 20 years of his career.

Walking tours take visitors past significant historical and architectural sites such as Wright’s home, the Frank Lloyd Wright Home and Studio. 

There is also the home of famed author Ernest Hemingway, who grew up in Oak Park. The Ernest Hemingway Foundation restored Hemingway’s home, and now tours of the author’s birthplace are given. Join a guided architecture tour to learn all about the history and creativity of the area’s top attractions!

Top sights here include:

  • Frank Lloyd Wright Home and Studio
  • Ernest Hemingway Birthplace Museum
  • Brookfield Zoo 
  • Oak Park Conservatory

There are lots of convenient ways to get from Chicago to this charming village. The train at Chicago OTC and the subway both head straight to Oak Park at inexpensive prices. The fastest way to get there would be a taxi, though this will run a little more costly than the subway or train. 

The Line 20 bus also comes here at an affordable price, though it will take longer to reach your destination as stops are included. 

Oak Park’s busiest month is from May to July. However, we recommend visiting anywhere from August to October if you want to avoid the crowds and high prices for these tourist-heavy months. 

Read next: The 21 Best Things To Do In St Louis, Missouri

7. Holland, Michigan

  • Distance from Chicago: 152 miles/245 km
  • How Long it Takes: 2½ Hours

Notorious for its award-winning breweries, Holland, Michigan, is only a few hours from Chicago and worth the trip. 

Holland’s natural beauty and charm are one for the books, with its lush nature, flower-speckled fields, and waterfront views.

The city is home to numerous parks to choose from for a picturesque stroll through nature with outstanding vistas. Holland’s downtown is thriving with locally-owned businesses to shop at.

The historic area was named one of “America’s Prettiest Towns” by Forbes magazine, with its cobblestoned sidewalks, live performances, and award-winning eateries and breweries to choose from. 

The Windmill Island Gardens is one of the top attractions in Holland. The gardens feature a 251-year-old windmill called De Zwaan. It is the only authentic Dutch windmill working in the nation.

Holland State Park is another largely popular attraction. The park showcases its iconic “Big Red” lighthouse for breathtaking sunset scenery and long stretches of beach on Lake Macatawa and Lake Michigan.

Many travel to the park to go camping, fishing, paddleboarding, sunbathing, and more for one of the best weekend trips from Chicago.

  • Windmill Island Gardens
  • Holland State Park
  • Holland State Park – Macatawa Campground
  • Big Lake Brewing
  • Saugatuck Dunes State Park

For those without a car, there is a direct connection by train from the Chicago Union Station to the Holland Amtrak Station. However, if you have a car or can rent one, that is the only other option to get back and forth to avoid ridiculous fees for a taxi. 

We recommend visiting Holland in spring when the flowers bloom to see the tulips that the area is known for. They usually bloom around late April and continue to bloom to mid-May.

Visiting Holland in the summer is extremely popular, so if you don’t mind crowds and want to catch some sun, take a trip to the city to soak in the sun and picturesque views. 

Holland Michigan

8. Peoria, Illinois

  • Distance from Chicago: 173 miles/267 km
  • How Long it Takes: 3 Hours

Nestled along the Illinois River, Peoria is a bustling shipping center and agricultural production zone. Presenting a suburban feel, the city has family-friendly attractions to savor. It was once known as the Whiskey Capital, with 40% of alcohol produced in the United States coming from Peoria in 1890. 

On the city’s historic Distillery Row along the Illinois River, visitors can taste Peoria’s specialized whiskey distilleries that have maintained the city’s legacy.

There is much to see and do in Peoria. Designed by Pritzker Prize-winning architects John Burgee and Philip Johnson, the Peoria Civic Center is a hotspot attraction in downtown Peoria. The center showcases an exhibit hall, an arena, and a theater that hosts live entertainment for comedians, Broadway shows, concerts, and more.

The Luthy Botanical Garden is a refreshing stroll through themed gardens, including a children’s, Japanese, rose, and herb garden. It was also the first botanical garden in the state.

For a fun new experience, hitch a ride on this guided architecture cruise to experience the iconic architecture along the Chicago River. 

Top things to do include:

  • Peoria Civic Center
  • Peoria Riverfront Museum
  • Louisville Slugger Sports Complex
  • Forest Park Nature Center
  • Luthy Botanical Garden

The cheapest method of getting to and from Peoria from Chicago is by driving. Another method of taking the train from the Chicago Union Station to Peoria Amtrak Station. This route will take longer than the alternative of going by car. 

The most popular time to visit Peoria is in the summer. However, if you’re looking for cooler weather, we recommend visiting the city in September to early October when the weather is getting cooler.

Read next: 23 Best Things To Do In Kansas City, Missouri

9. Michigan City

  • Distance from Chicago: : 60 miles/96 km
  • How Long it Takes: 1 Hour 15 Minutes

The source of Michigan City’s name is initially confusing for many. The city was not named after the state of its namesake but Lake Michigan that it is near. Michigan City is a favored tourist spot thanks to its convenient location near top attractions such as Indiana Dunes National Park and Lake Michigan. 

The city has a rich history with a small-town charm, and history buffs will be pleased to find the city flooded with attractions.

The historic city preserves its oldest structure, a lighthouse established in 1858, at the Old Lighthouse Museum. It was the home of the creator of Wikipedia, Howard G. “Ward” Cunningham, who grew up in the city.

The Barker Mansion is an English manor built in 1857, preserving period furnishings from the Gilded Age. It is part of the National Register of Historic Places and is open for tours.

Michigan City is a rewarding day trip from Chicago. Other than its historical attractions, there are nature-based activities such as Friendship Botanic Gardens and Indiana Dunes National Park. Go for a relaxing evening or tour the vineyards at Shady Creek Winery. Or test your luck at the Blue Chip Casino Hotel Spa.

Top attractions include:

  • Washington Park Zoo
  • Friendship Botanic Gardens
  • Shady Creek Winery
  • Blue Chip Casino Hotel Spa
  • Michigan City Lighthouse and Pier

In Chicago, there are direct routes to take on the buses and trains that head to Michigan City from Chicago. Other than that, the only other inexpensive way to reach Michigan City is by driving. 

Ideally, summer or early fall in September is the best time to visit Michigan City to savor outdoor activities while in town.

Unfortunately, the winter months are frigid, from November to February. Therefore, we recommend not visiting during these months if you plan on spending time outdoors at the parks or gardens. 

Michigan City Pier

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Anderson Japanese Gardens

The 23 most unique day trips from Chicago

Break the mold with these under-the-radar, kitschy or otherwise unique trips within a few hours' drive of Chicago.

When it comes to a much needed escape from the city, there are countless day trips from Chicago if time doesn’t allow for a full weekend getaway . And luckily for the adventurous and curious, there are plenty of opportunities to swap typical activities like kicking back with brews for hiking  among bison or spelunking in an ancient cave. Many sites and experiences within driving distance of Chicago take you far beyond the norm, from year-round Christmas at an amusement park to (not so similar) replicas of some of the world’s most celebrated cultural sites. Midwesterners may love their weekend lake house tradition, but they also love the wacky, meaningful and unexpected. Here are the most unique day trips from Chicago.

RECOMMENDED: The best lakefront Airbnbs near Chicago

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The most unique day trips from Chicago

Explore the country’s largest magic museum

1.  Explore the country’s largest magic museum

Driving time from Chicago: About three hours

You'll find everything from obscure conjuring tomes to equipment used in Harry Houdini's most famous escape acts at the American Museum of Magic in Marshall, Michigan, home to the biggest collection of magic ephemera in the United States. With more than 350,000 artifacts onsite, there's more than enough magical entertainment to fill an afternoon: Take a self-guided tour through magic history, try to squeeze into a replica of Houdini's Milk Can Escape or book an appointment at the museum's Lund Memorial Library to pore over archival materials.

2.  Spot bison at Midewin National Tallgrass Prairie

Driving time from Chicago: About one hour

Want to get a firsthand look at why Illinois is nicknamed the Prairie State? Take a trip southwest of the city to Will County, where a herd of bison roam the 9,000-acre expanses of the Midewin National Tallgrass Prairie as part of an ongoing habitat restoration project (the area once housed the Joliet Army Ammunition Plant and bunkers still remain). Spotting the herd isn't a sure thing—it's a massive park, after all—so you're best off bringing a pair of binoculars and starting at the Iron Bridge Trailhead, which puts you closest to the bison pasture area. From there, a three-mile round trip hike will lead you to an overlook point outfitted with viewing scopes and benches to rest on.

Go spelunking inside Cave of the Mounds

3.  Go spelunking inside Cave of the Mounds

Wander among soda straws, flowstones, helictites and other stunning geological formations inside of Cave of the Mounds, a natural limestone cave near Blue Mounds, Wisconsin. Once home to a limestone quarry, the cave is now open for guided (or self-guided) tours through mineral deposits in shades of white, reddish brown, black, purple and gray. Fun fact: Whether you're visiting on a hot summer day or during the frigid depths of winter, the subterranean expanse is always a cool 50 degrees, so be sure to dress accordingly.

See the Batmobile (and tons of other famous cars) at the Volo Auto Museum

4.  See the Batmobile (and tons of other famous cars) at the Volo Auto Museum

Driving time from Chicago:  About an hour and a half

Don't think that you're a car person? A visit to the Volo Auto Museum just might change your mind. Throughout this suburban attraction's 33 exhibits, you can ogle everything from '50s-era Thunderbirds and Oldsmobiles (Vintage Cars), to Britney Spears' 2006 Mercedes-Benz and Elvis Presley's 1974 Cadillac (Cars of the Rich and Famous), to Scooby Doo's Mystery Machine and the Subaru driven by Paul Walker in Fast & Furious 7 (TV and Movie Cars). There's even an entire exhibition dedicated to different iterations of the Batmobile. Plus, if you're really hoping to find some artifacts that aren't car-related, check out the museum's collection of planes, antique card games, animatronics and music machines, or shop for new home decor at the nearby Volo Antique Malls.

Tour modernist architecture in Columbus, IN

5.  Tour modernist architecture in Columbus, IN

Driving time from Chicago: About four hours

Thanks to a highly successful funding program in the mid-20th century, the small-ish town of Columbus, Indiana is home to some of the Midwest's most stunning examples of Modern buildings, structures and public art, with works by Eero Saarinen, I.M. Pei, Richard Meier and other architectural luminaries dotting its downtown thoroughfares. You can pay for a guide to lead you through the highlights, but the town also offers a free audio tour app that leads listeners through 18 of the most prominent buildings in the area.

Paddle along the African American Heritage Water Trail

6.  Paddle along the African American Heritage Water Trail

Driving time from Chicago: About 40 minutes 

Chicagoans who love active, experiential learning can take an impactful day trip of paddling through history along the Little Calumet River, a waterway which, along with others, connects Lake Michigan with the Mississippi River. In a span of just seven miles, experience nearly two centuries of African American history, from the underground railroad and civil rights to the birth of environmental justice. Beginners can join an organized group paddle during the summer season while experienced water recreationists can follow a self-guided paddle outlined on the Openlands website .

7.  Hike around the iconic Farnsworth House

Driving time from Chicago: About an hour and a half

Located in Plano, Illinois at the banks of the Fox River, the glass-walled Farnsworth House—designed by Bauhaus architect Ludwig Mies van der Rohe as a weekend retreat for Dr. Edith Farnsworth—is both a National Historic Landmark and one of the area's foremost examples of Modernist architecture. Though the house has been besieged by floods throughout its 70-year history, ongoing preservation efforts have kept it in tip-top condition. Book a docent-led tour through the building (the summertime moonlight tours, which commence at dusk and loop around a lighted exterior path, are an especially beautiful option) and take some time to soak in the natural beauty of the home's 60-acre wooded grounds.

Check out Amish Country in Shipshewana, IN

8.  Check out Amish Country in Shipshewana, IN

Driving time from Chicago: About two and a half hours

Escape the bustle of city life among the placid streets of Shipshewana, a teeny town nestled in the center of northern Indiana's Amish Country. Kick off your day with a tour of Menno-Hof—a museum dedicated to Amish and Mennonite history—or book a sight-seeing expedition aboard a horse and buggy, then fuel up with traditional Amish eats at family-style restaurants like A Taste of of Shipshewana (where you'll also find live cooking and quilting demonstrations). In the market for antiques and tchotchkes? Plan a visit on Tuesdays or Wednesdays from May through September, when the town hosts the Midwest's largest flea market.

Explore the Bahá'í Temple

9.  Explore the Bahá'í Temple

Driving time from Chicago: Around 30 minutes

No doubt you’ve seen pictures or driven by the striking Baha’i House of Worship in Wilmette, but make a day of it and actually witness the interior details. The temple of the Baha’i faith was built in 1953 after 50 years of planning and construction. It is currently open to the public daily with free admission to the temple’s domed auditorium and surrounding gardens.

10.  Wander through a Tudor-style castle in Oregon, IL

View this post on Instagram A post shared by Nicholas Underhill (@nick_underhill02)

Driving time from Chicago:  About two hours

Back in the late 1920s, Chicago Daily News publisher and owner Walter A. Strong began construction on a Tudor-style manor to serve as his family's summer home. The end result—a 10-bedroom, 8-bathroom behemoth with a couple of secret passages to boot—can be explored in the present day through an hour-long tour, which covers the history of the Strong family, the castle's architecture and a brief history of medieval life. If you're got time after the tour, head to the nearby Castle Rock State Park (unaffiliated with the aforementioned castle, in case you were wondering) to hike among gorgeous sandstone bluffs.

See the Great Pyramids without leaving Illinois

11.  See the Great Pyramids without leaving Illinois

Driving time from Chicago: About one hour and five minutes 

One of the most unexpected I-94 sights is the Gold Pyramid House, a 1970s-era family compound featuring replicas of the Great Pyramid of Giza, a 55-foot statue of Ramses II and King Tutankhamun’s tomb. Full of objects and decor leaning from kitschy to cult-like, visitors can meander the grounds and attend events, and even take home Gold Pyramid Water and Gold Pyramid Vodka as souvenirs, though it’s unclear whether either were on sale in ancient Egypt. House tours on select Saturdays and by appointment only. 

Meander through an English-style village next to the largest inland oil refinery

12.  Meander through an English-style village next to the largest inland oil refinery

Driving time from Chicago: About 35 minutes 

Marktown Historic District may not be one of the seven wonders of the world, but it's certainly a marvel of Northwest Indiana. Built in 1917 as a planned worker community by renowned architect Howard Van Doren Shaw—10 years after the last home was sold in nearby planned community Pullman—Marktown became famous after its appearance in Ripley's Believe It or Not! for being  the only town in North America where cars park on the sidewalk and neighbors walk on the streets. Today, the quaint Tudor revival-style homes with bright colors and cheerful window boxes are in eerie contrast to the surrounding heavy industry. Learn about architecture and the area’s history in steel on a self-guided tour.  Then, refuel at Hegewisch favorite Pudgy’s Pizza before heading home.

Ride a vintage train at the Illinois Railway Museum

13.  Ride a vintage train at the Illinois Railway Museum

The country's largest railway museum sits just outside the Chicago metropolitan area in Union, Illinois, where you can check out a massive collection of antique train cars and hop aboard working streetcars, steam and diesel trains that loop around the 100-acre campus. Plan for an entire day of exploration: The museum's buildings house all kinds public transportation artifacts, including an 1859 horse-drawn streetcar, every kind of CTA 'L' car and a display of working railroad signs and signals.

Take a nature walk through Cantigny Park

14.  Take a nature walk through Cantigny Park

Driving time from Chicago: About 45 minutes

This verdant Wheaton park—formerly the estate of the publishers of the Chicago Tribune— offers 29 acres of gardens and 160,000 plants, complete with two and a half miles of nature paths perfect for a leisurely afternoon stroll among the flowers. Military history buffs will also want to check out the First Division Museum on the park's grounds, which chronicles U.S. military history from World War I to the present.

Find your zen in the Anderson Japanese Gardens

15.  Find your zen in the Anderson Japanese Gardens

Driving time from Chicago: About two hours

Once you've thoroughly explored the lovely Garden of the Phoenix in Jackson Park, set your sights on a visit to the Anderson Japanese Gardens in Rockford. Designed by landscape architect Hoichi Kurisu, the 12-acre gardens feature trails, waterfalls, tranquil ponds, gravel gardens and an abundance of Japanese maples, among other plant life. Plan ahead and book the "Frank Lloyd Wright Meets 16th Century Japan Tour" that guides visitors through the garden's 16th century Sukiya-style tea house and the Laurent House, which has the distinction of being the only home Wright designed for a client with a physical disability.

Learn about America’s RVs at a niche museum

16.  Learn about America’s RVs at a niche museum

Driving time from Chicago: About two hours 

Get inspired to embark on your version of the great American road trip as you browse permanent collections of trailers, motorhomes, housecars and more ranging from the 1910s to present at Elkhart’s RV/MH Hall of Fame (RV/MH stands for recreational vehicle and manufactured housing). Step back in time with Instagram-worthy vintage airstreams, Model T campers and motorhomes that look like they stepped off the set of Stranger Things . After your visit, explore the thousands of archives at the RV/MH Library, where you can glimpse into the recreational lives of North Americans in the 1960s issues of Trailer Life or 1980s issues of Camping Today .

Visit Frank Lloyd Wright's home and studio

17.  Visit Frank Lloyd Wright's home and studio

Just outside the city limits is the birthplace of Frank Lloyd Wright’s iconic architectural style. Early design concepts are filled in Wright’s Oak Park home and studio, with the surrounding residential district containing the most Wright-designed homes in the world. Visitors can enjoy a guided interior tour of the residence as well as a walking tour of the neighborhood for just $30 per person. Afterwards, pick up your favorite breads and pastries at Publican Quality Bread's Oak Park outpost.

Take a picture with a (smaller) Leaning Tower of… Niles

18.  Take a picture with a (smaller) Leaning Tower of… Niles

Driving time from Chicago: About 25 minutes 

Sitting at a half the size its original at 94 feet tall and leaning 7.4 feet, the replica of the Leaning Tower of Pisa in suburban Illinois is an unlikely site and guaranteed out-of-the-box day trip. In the 1930s, a local businessman wanted to disguise a water tower and the answer was—obviously!—to craft a leaning tower. Taking an illusion photo holding up the tower is a must, and if you’re not too tired, head to nearby North Branch Trail and surrounding forest preserves for nature spotting or cozy up with your next great read at New Book Joy .

Watch an outdoor play at American Players Theatre

19.  Watch an outdoor play at American Players Theatre

Driving time from Chicago: About three and a half hours

Spring Green, Wisconsin is perhaps best known as the home of Taliesin, Frank Lloyd Wright's Prairie style summer estate set amid the limestone outcroppings of Wisconsin's Driftless Area. You should make a stop at the house if you have time—Wright's estate offers a huge variety of guided tours—but the 1,089-seat outdoor ampitheater at American Players Theatre is an equally unbeatable summertime attraction. The company's repetoire is mostly classical , though you'll find more contemporary works on the lineup as well.

Celebrate Christmas in July at Santa’s Village

20.  Celebrate Christmas in July at Santa’s Village

Driving time from Chicago: About an hour

Sure, Six Flags is fun, but there's only one suburban amusement park where you'll run into Santa Claus year-round, and that's Santa's Village Azoosment & Water Park in East Dundee. Despite its wintry theme, the family-friendly park is best visited in summer: Splash around in the Caribbean Christmas-themed Santa Springs water park—featuring two 300-foot, candy cane-colored slides—or take a spin on thrill rides like the Blizzard, which swings riders 40 feet in the air on a spinning pendulum.

Eat fried chicken on Historic Route 66

21.  Eat fried chicken on Historic Route 66

Driving time from Chicago:  About 35 minutes

Fried chicken with a side of history? We’ll take it. At Dell Rhea’s Chicken Basket, you’ll be eating food that has been satisfying hangry travelers and folks simply looking for a good meal since 1946. This gas station lunch counter-turned-dining room is conveniently located off Route 66, its gleaming lights a beacon for those traveling to or from Chicago. Listed on the National Register of Historic Places, step into the nearly unchanged brick building and devour a Famous Fried Chicken Dinner, hand breaded and deep fried half chicken served with mashed potatoes and biscuits.

Say “prost” in Germantown, WI

22.  Say “prost” in Germantown, WI

Despite its name, the Milwaukee suburb of Germantown, Wisconsin doesn't quite have the transportative qualities of other places in the Midwest that look like Europe . Still, there's a lot to love about this historically German settlement—sip a stein full of Krombacher Pils at the Von Rothenburg Bier Stube , check out more than 5,000 antique bells at the Sila Lydia Bast Bell Museum & Fire Hall or don your best lederhosen/dirndls for Maifest, the annual three-day festival held in honor of the beginning of spring.

See some giant things in Casey, Illinois

23.  See some giant things in Casey, Illinois

Just under four hours south of Chicago, the intriguing town of Casey prides itself on being filled to the brim with giant things—literally. The town is home to 12 of  world’s largest items . From a 28-foot Chevy truck key to a 42-foot long wind chime to a 46,000-pound rocking chair behemoth, these public sculptures are really one-of-a-kind.

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Learn how to easily plan your dream trip to the Midwest!

Chicago skyline at sunset.

15 Best Day Trips From Chicago Worth The Effort

August 13, 2022 by //  by  Midwest Explored 1 Comment

Are you looking for the best day trips from Chicago that are actually worth the effort? Then this list is for you!

Maybe you want a break from the city, or maybe you just want to explore a new city.

Planning your trip to Chicago last minute?

Make sure to book ahead. Hotels and tours often sell out the closer you get to your trip. Here are our top pics for Chicago!

Top Experiences And Tours In Chicago:

  • Chicago River Architecture Cruise (Skip the Ticket Office!)
  • Willis TowerSkydeck & The Ledge Ticket (Elevator express entry!)
  • Navy Pier Centennial Wheel Ticket (Panoramic views of Chicago!)
  • Big Bus Hop on Hop Off Sightseeing Tours (24, 48, or 72-hour options available.)

Hop Hotels In Chicago:

  • Eurostars Magnificent Mile (In the heart of Chicago!)
  • The Peninsula Chicago (Near museums)
  • Club Quarter Hotels Wacker (Overlooking the Chicago River!)
  • Hotel Blake (Close to Millennium Park.)

No matter your interests you’ll find a great day trip option on this list.

I’ve found some of the most unique, fun, and adventurous day trips to make from Chicago.

There are beautiful state parks, metropolitan cities, unique and charming small towns, and so much more.

So, lets take a look at the 15 Best Day Trips from Chicago Worth The Effort!

Chicago Illinois skyline at sunset

Cedarburg, Wisconsin

In just under 2 hours, you can find yourself in the charming small town in Wisconsin called Cedarburg.

Cedarburg is an excellent day trip from Chicago for those looking for small-town charm, but with plenty of activities.

Because Cedarburg is know for its small town atmosphere, you’ll find some really unique shops and resturants.

There is a Candy Kitchen, an Amish Craftsmen Guild, stores full of items made by local artisans, and even a shop where you can search for unique gemstones.

Cedarburg also has a wide variety of unique museums.

There is a local art museum, a local history museum, a woolen mill and textile museum, and even a museum depicting early life in Cedarburg.

No matter your interests, Cedarburg is guaranteed to have something fun for you to do, and you’ll find it was worth the drive.

Large vintage house in Cedarburg on water in autumn, day trip from Chicago.

Rockford, Illinois

If you drive for about an hour and a half West of Chicago, you’ll find yourself in Rockford Illinois.

The best way to describe Rockford is to call it a big-little city. It’s the fourth largest city in Illinois, but still feels welcoming in a small-town sort of way.

Rockford is also bursting with things to do.

Music lovers will enjoy checking out one of the many spots home town band Cheap Trick helped make famous.

If museums are more your thing, don’t worry, Rockford has those too. Stop by the Burpee Museum of Natural History or the Discovery Center Museum.

If none of that sounds interesting, then maybe you’ll like the Anderson Japanese Garden. It is consistently rated as one of the best Japanese Gardens in North America.

There is so much to do that you may want to turn your day trip into a Midwest weekend getaway . With the endless list of activities in Rockford, it absolutely makes it worth the hour and a half drive from Chicago.

A waterfall at the Japanese Garden in Rockford Illinois, a daytrip from Chicago.

Grand Rapids, Michigan

Grand Rapids Michigan is one of the perfect day trips from Chicago for lovers of art, food, and beer.

In fact, Grand Rapids is known as Beer City USA.

For those who want to take full advantage of all Beer City USA has to offer, you’ll want to download the Brewsader App.

The App gives you a full map of all the breweries in Grand Rapids, and after you check in at 8 of them, you’ll earn a fun Brewsader shirt to commemorate your trip.

If beer isn’t your thing, not to worry.

There are still some absolutely amazing and unique restaurants in Grand Rapids you can check out. Or you can stop into one of the cities popular art galleries.

There really are so many cool things to do in Grand Rapids .

Ariel view of Grand Rapids, a Chicago day trip, illuminated at sunset.

Oak Park, Illinois Is One Of The Best Day Trips From Chicago

Oak Park Illinois is the shortest distance you’ll have to travel for a day trip on this list as it’s just under 20 minutes outside of Chicago.

Despite that, many people in Chicago, or even visiting Chicago, don’t think to explore Oak Park.

Admirers of Frank Lloyd Wright, one of America’s most prominent architects will know Oak Park though.

Wright called Oak Park home, and left his mark on many of the cities most popular homes and buildings.

Oak Park was also home to another famous architect, George W. Maher, who also designed many of the cities most prominent homes and buildings.

Ernest Hemingway was also born in Oak Park, and you can visit his childhood home that has now been turned into a Hemingway Museum.

Book Tickets Here: Ernest Hemingway Boyhood Tour

Because of Oak Park’s proximity to Chicago, many gangsters in the early 20th century called the area home, and you can now take a Gangster tour.

Oak Park is a tremendously unique option for a day trip from Chicago and you don’t even have to travel far!

An architectural marvel, a Frank Lloyd Wright home in Oak Park with manicured front lawn.

Michigan City, Indiana

Michigan City Indiana is about an hour away from Chicago, and you’ll spend the whole trip driving along Lake Michigan.

So it’s no surprise that Michigan City also has its fair share of lighthouse history.

In Michigan City you’ll be able to explore the Old Lighthouse Museum and even take a tour of the Michigan City Lighthouse and Pier.

Stroll along the beach or maybe head over to the Washington Park Zoo, which is full of more interesting architecture, and of course animals.

Travelers also enjoy touring the Barker Mansion and sipping on local wines at some of the best wineries in Indiana

Michigan City lighthouse white with red roof on Lake Michigan, a Chicago day trip.

Monroe, Wisconsin

Monroe Wisconsin is the Swiss Cheese Capital of the USA, and just over 2 hours away from Chicago.

Cheese lovers will delight in the many, many, cheese related activities that abound in Monroe.

Monroe is a cute small town that takes cheese very seriously, and for good reason. The city has thrived for over 100 years because of it’s cheese industry.

You can pair some locally made cheeses with local beers or just explore the numerous cheese shops.

Or watch a movie at the local drive-in theater while munching on cheese curds.

The small town even holds a yearly Cheese Days Festival where you can sample all of the local cheeses while sipping a cold local beer.

Monroe is perfect for your next day trip from Chicago the next time you’ve got a serious craving for all things cheese.

This cool town is one of the best places to visit in Wisconsin.

Vintage downtown in Monroe, Wisconsin.

Kankakee, Illinois

Kankakee Illinois is a cute town in Illinois just over an hour south of Chicago.

It’s full of small town charm but it still has a lot of interesting things to do, making it perfect if you’re looking to escape the city for a day.

One of visitors favorite things to do in Kankakee is taking a tour of the B. Harley Bradley House, a famous house designed by Frank Lloyd Wright.

Kankakee is also amazing for those looking for a little outdoor adventure.

The entire Kankakee County and parts of the city of Kankakee are bursting with outdoor activities.

You can enjoy some of the best hiking in Illinois , along with canoeing, kayaking, and even scuba diving in the Haigh Quarry.

Kankakee is one of the best day trips from Chicago Illinois if you’re looking for fresh air, beautiful views of nature, and plenty of small-town charm.

Kankakee River waterfall rushing over rocks. Great Chicago day trip.

New Glarus, Wisconsin

America’s Little Switzerland is in New Glarus Wisconsin, just 2 and half hours outside of Chicago.

New Glarus is a small town that loves beer, cheese, and festivals. In the warmer months, they may have 3-4 festivals a month.

Typical New Glarus festivals include Polkafest, The Beer, Bacon, & Cheese Festival, The Heidi Folk Festival, Blues Brews & Food Trucks Festival, Maxwell Street Days, and so many more.

New Glarus is also known for having a selection of brews that you can only buy in Wisconsin, and some of them you can only buy in New Glarus.

If you are a beer connoisseur, you’ll love checking out one of the local beer gardens. And if you decide to stay longer here are some epic Wisconsin Airbnbs to look into.

Foodies will love checking out one of the many restaurants that serves up Swiss and Swiss inspired fare.

New Glarus is a cute romantic getaway in Wisconsin!

Quirky beer garden made of stone,  in New Glarus, WI.

Holland, Michigan

Holland Michigan is a little over 2 hours away from Chicago and is one of the best day trips from Chicago that is definitely worth it.

Named after the home country of it’s original settlers, Holland is bursting with Dutch charm.

In the Spring it’s host to the Tulip Time Festival where you will get to see a riot of colorful tulips with a windmill that is straight from Holland.

Even if you can’t make it to the Tulip Time Festival, you’ll love exploring this cozy small town.

There are plenty of unique shops, restaurants, breweries, and unique Dutch gardens.

Holland is also home to one of the coolest lighthouses in Michigan , The Big Red Lighthouse.

Visitors love to view the iconic lighthouse standing proudly on it’s pier, with the bright red façade making a striking contrast against Lake Michigan.

Holland is a small town in Michigan full of charm that is definitely worth the effort to visit, any time of year.

Brilliant yellow tulips in foreground with European-inspired red brick building in background in Holland MI.

Milwaukee, Wisconsin

If you are looking to explore a city, but you want a break from Chicago, then I suggest driving the hour and half to Wisconsin’s largest city, Milwaukee.

Because Milwaukee is Wisconsin’s biggest city, it is full of unique things to do making it one of the best day trips from Chicago!

And there are so many things to do in Milwaukee!

If you’re on a budget, take a stroll down the streets and admire the many murals on the sides of buildings. Or go window shopping and one of the many boutique stores.

You can also check out a play or musical, go on a boat tour of Milwaukee, or explore one of the amazing restaurants in Milwaukee.

If you’re a sports fan, you may want to check out one of Milwaukee’s home teams. Afterwards, you can talk about the game at one of the cities awesome bars or resturants.

Milwaukee is an amazing city that often gets overlooked, but you won’t regret making the trip out there.

An aerial view of illuminated Milwaukee WI with sunset in background, one of the best day trips from Chicago.

Oglesby, Illinois

In just under two hours you can be in beautiful Oglesby Illinois.

Oglesby is perfect for day trippers looking for a break from the city as it is home to two beautiful State Parks.

If you’re looking for some outdoor adventure and clear air, then you’ll find that this is one day trip that is worth the effort.

At Starved Rock State Park you’ll find trails that lead you along the Illinois River and into steep sandstone canyons.

It is Illinois’ most popular State Park and for good reason. It’s accessible for all skill levels and you get to experience some beautiful views.

The other state park near Oglesby is Matthiessen State Park. The entrance for this park is just a few miles South of Starved Rock State Park.

Matthiessen State Park has similar views, but it is often far less crowded.

It is a great choice to experience fall in Illinois.

You’ll still be able to hike beautiful trails, see gorgeous Illinois waterfalls, and enjoy nature, but you’ll be far less crowded.

If you have plenty of time on one of your day trips from Chicago Illinois, you should definitely check out both state parks.

Large rock formations in water in park in Oglesby IL.

Lake Geneva, Wisconsin

Lake Geneva is a Wisconsin town about an hour and a half outside of Chicago.

It has a history of being the go-to spot for Chicago’s wealthy families during the summer.

Lake Geneva is a beautiful small town that thrives because of the large Lake Geneva, and it’s a budget-friendly day trip option.

There are so many things to do in Lake Geneva all year long that include lake activities.

But you’ll also find a charming town full of unique boutiques, restaurants, and even outdoor activities like hiking and snow sports in the winter.

In early February the town holds a Winter Fest which features the only snow sculpting championship in the United States.

Visitors get to experience massive snow sculptures, food from local restaurants, and so much more – and it’s free to attend!

In the summer, enjoy boating, swimming, and kayaking on Lake Geneva before having a meal at one of the amazing local restaurants in Lake Geneva .

No matter what time of year you visit, Lake Geneva is a Chicago day trip that is worth the effort.

Vintage downtown Lake Geneva, WI, one of the best day trips from Chicago.

Highwood, Illinois

Highwood Illinois is another small town that goes big when it comes to festivals.

Just 35 minutes North of Chicago, this charming small town is the perfect day trip from Chicago Illinois for festival lovers

There’s almost a festival every month, and they all have different themes.

For foodies, there is a Taco Festival, a Bloody Mary Festival, and a Garlic Festival.

There are also smaller music festivals, fun runs, and a Pride Festival.

One of Highwood’s most iconic festivals though is probably The Great Highwood Pumpkin Festival every October.

It is one of the coolest things to do in Illinois .

The Festival benefits the Make-A-Wish Foundation and attendees get to check out rows and rows of carved pumpkins.

Attendess of Pumpkin Fest can even bring their own pumpkins and carve them before adding them to the walls of carved pumpkins.

Highwood is a truly unique town, full of really cool festivals that are sure to make the trip out there worth the effort, no matter what time of year you go.

Rows of orange pumpkins at Pumpkin Fest in Highwood, IL.

Indiana Dunes National Park, Indiana Is One Of The Best Day Trips From Chicago

Just under an hour outside of Chicago, the Indiana Dunes National Park is one of the coolest national parks in the Midwest.

The Indiana Dunes National Park is on 15 miles of beach on Lake Michigan’s South shore.

It is a nature lover’s dream with over 15,000 acres of preserved land full of unique hiking trails, wetlands, prairies, woodlands, and of course beaches.

From Memorial Day to Labor Day, there is a $6 entrance fee to enter the park. During the ‘off season’ though, it’s free to enter.

The Indiana Dunes is full of fun things to do, and you could spend days exploring the park making it a fun weekend getaway in Indiana!

It’s a beautiful spot, and it is definitely one of the day trips from Chicago that is worth the effort.

White sandy beach with sea oats and waves rolling in at Indiana Dunes National Park, a great Chicago day trip.

Madison, Wisconsin Is One Of The Cool Day Trips From Chicago

In just over two hours you can find yourself in Madison Wisconsin.

If you’re looking for a fun Chicago day trip in the summer, Madison is perfect for you.

With five lakes, spanning over 15,000 acres, in summertime there are so many things to do in Madison.

There are water sports, festivals, water front dining, and so much more.

But Madison isn’t just a fun place to visit in the summer.

You’re sure to find fun no matter what time of year you go.

There are dinner theaters, breweries, delicious restaurants, and unique boutiques. Put treating yourself at some of the restaurants in Madison on your list!

You’ll find that Madison Wisconsin is one of the most entertaining day trips from Chicago that is definitely worth the effort.

The skyline of Madison WI at sunset.

Packing List For Daytrips From Chicago

Here are some  tips on how to pack lightly

A  concealed travel pouch  may be one of the most important items you bring along when on one of your Chicago day trips! 

It is  always   important  to protect your personal information. Identity thieves are everywhere.

This  unisex RFID blocking concealed travel pouch is  lightweight and comes in several colors. It has lots of organization to give you peace of mind.

You can place it under your clothes next to your body to carry your ID safely.

If you have a pouch already that does not come with the RFID protection, as I do, these  RFID  sleeves  are the perfect solution.

This configuration comes with enough credit card sleeves that the entire family would be protected. They are slim too, so they will easily fit into your pouch or wallet. 

If you are planning on taking a lot of pictures with your phone you will definitely want to consider an  external charging battery .

This  Anker high-speed phone charging battery  is  the exact one  I carry with me on all of my trips.

It can be used on a variety of phones, not just an iPhone like I have. And wow is it fast!

I like that it holds its charging capabilities for several uses so I do not have to worry about it while out and about, and if I forget to recharge it at night, it will still be good to go the next day.

My daughter gifted me with this  FugeTek selfie stick and tripod   setup for my birthday. I absolutely love it!

It is made of lightweight aluminum and so easy to use.

It has Bluetooth connectivity and is a breeze to use for taking selfies with all those nature shots while on your Chicago day trips..

Hydration is so important when hiking. You want to remain hydrated throughout your hikes to support your immune system which in turn will be stronger to fight off any germs you will encounter during your travels. 

You will want to bring your own  refillable water bottle  with you. 

I never leave home on a trip without my  Bobble filtration bottle .  The 18.5-ounce size is perfect for hiking and it fits nicely in the pocket of a backpack.

When filled with water, it is not too heavy to carry. And the charcoal filter ensures fresh clean water whenever you fill the Bobble.

Perhaps you are traveling a long distance to Chicago Illinois and packing space is a premium in your suitcase, or in your car.

Then this  set of collapsible silicone foldable water bottles  would work well for you. Would not take up much space at all. 

You will want a  backpack or daypack  with you to store snacks, your water bottle, phone, extra clothes, etc.. when on one of your day trips from Chicago Illinois. No matter the time of day or evening.

This   foldable water-resistant backpack   would be great

It is very affordable and is available in many color options for you to choose from. The fact that it folds down into a zippered pouch will make it easy to pack!

I hope you enjoyed this list of the 15 Best Day Trips From Chicago Worth the Effort! There are so many great big cities and little towns outside of Chicago just waiting to be explored.

If you are spending a weekend in Chicago , one of these trips from Chicago would def be fun!

If you take a trip to one of these awesome places, I’d love to hear about it in the comments!

Bright orange leaves on tree tunnel

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The Planet D: Adventure Travel Blog

21 Best Day Trips From Chicago In 2024

Written By: ThePlanetD Team

United States

Updated On: February 19, 2024

Welcome to the Windy City! Whether a local or a traveler eager to explore beyond the skyline, our guide to the best day trips from Chicago is your ticket to adventure. We’ll show you how to swap city streets for scenic escapes, all within a day’s reach of Chicago. From charming small towns to natural wonders, get ready to discover the Midwest’s most unforgettable experiences. Pack your sense of adventure, and let’s hit the road – Chicago-style day trips await!

Table of Contents

Incredible Day Trips from Chicago

Top Day Trips from Chicago

In this guide, we give you ideas for the top day trips from the third most populous city in the US. Located on the shores of Lake Michigan, many places will tempt you away from the city center. After exploring all of the awesome things to do in Chicago , from the Chicago River to historic landmarks, head to these fantastic places located within easy reach of the city.

The city is ideally located with easy border-crossing into Wisconsin, Michigan, and Indiana. It is also a great starting point for a day trip further south into central Illinois. You have four states at your fingertips – so you should carve out time for a day trip while visiting.

1. Milwaukee, WI

chicago day trips by train

Milwaukee is a big deal. This major city is located on the shores of western Lake Michigan in Wisconsin – just a 1.5 hour train ride or drive north of Chicago. We’d suggest catching the train if possible, as Milwaukee is best known for its breweries. Taking guided brewery tours is one of the  best things to do in Milwaukee . Aside from its alcohol, though, it is also home to the Holler House and Milwaukee Art Museum. Don’t forget the Harley-Davidson Museum, which hosts a beautiful display of motorcycles and documents iconic biker culture. The Milwaukee Public Museum also has a large-scale European village.

If you want a fantastic day out from Chicago, Milwaukee is ideal. It has a strong sense of culture and many niche pockets of interest, like Harley-Davidson bikes and breweries. It is also a breeze to reach by train or car.

  • Distance from Chicago: 1.5 hours
  • How to get there: Train, bus or coach

Suggested Tour: A Group Tour to Discover Milwaukee

2. south bend, in.

Day Trips from Chicago South Bend IL

South Bend has a different vibe as a university city on the St. Joseph River. It is fantastic if you are looking for a more sedate city experience. You can visit the University of Notre Dame’s iconic campus, with its classic gold-domed building. There’s also plenty of local history that you can experience in the city center, like car manufacturing from years gone by at Studebaker National Museum and the regional history at the History Museum.

South Bend is definitely slower-paced than quick-footed Chicago. However, it has lots of attractions too. Think of it as a relaxing and intellectual place to spend a day sightseeing. It has lots of fun and student twists, like cheap bars and coffee spots.

The city is located just east of Chicago, on the other side of Indiana Dunes National Park, and on the lower east shore of Lake Michigan. It is best reached by car, and we’d recommend stopping off at the national park en route.

  • Distance from Chicago: 2 to 3 hours
  • How to get there: Car or train

3. Madison, WI

Day Trips from Chicago Madison IL

Small Madison might not seem capital-worthy, but it is actually the capital city of Wisconsin, not the major, sprawling giant of Milwaukee. This smaller city has beautiful architecture galore. You can get up close to the historic domed Wisconsin State Capitol and walk the Capital City State Trail to sightsee different city attractions. There’s a botanic garden experience, too, at Olbrich Botanical Gardens, plus a quirkier downtown area with bars and coffee shops. Madison is your best choice if you fancy a political sightseeing day trip from Chicago.

Madison is also beautifully located next to two huge lakes – Lake Mendota and Lake Waubesa. Summer leaves plenty of opportunities for water sports and sunny waterfront hiking trails. Follow this walking tour to see the city’s architecture including the State Capitol, Der Rathskaller, Bascomb Hill, and Memorial Union.

  • Distance from Chicago: 2 to 4 hours
  • How to get there: By car or shuttle bus

4. Starved Rock State Park, IL

Day Trips from Chicago Starved Rock State Park IL

Starved Rock State Park is one of the most popular attractions in Illinois. The park sits on the banks of the Illinois River and holds a collection of sandstone canyons amidst beautiful forests. The canyons were initially cut with glacial meltwater, and you can explore the scenery using a network of clearly marked wooden boardwalks. Starved Rock State Park also has tons of waterfalls, which get impressively powerful in wetter months.

Nature lovers will adore this day trip choice. Not only is the natural scenery astounding, but you can also spot wildlife like white-tailed deer and bald eagles. Starved Rock State Park covers over 2,600 acres and has 13 miles of trails, with 18 canyons to admire. It is located inland from Chicago and Lake Michigan.

  • How to get there: Car

5. Cedarburg, WI

chicago day trips by train

Cedarburg has serious charm. It has old-school-style houses and is frequently compared to a movie set. The town was founded in the 1840s by a mixture of predominantly Irish and German settlers and is now considered a suburb of Milwaukee. Cedarburg has many cute and aesthetic things to do, with the bonus of brewery and winery tours. You can walk the vineyards and tour brewing rooms or head to unique attractions like the Wisconsin Museum of Quilts and Fine Arts. Cedarburg is a real gem and beats to its own drum, making it a memorable day trip from Chicago.

This Wisconsin town is located just north of Milwaukee’s city center. It is best reached from Chicago by car, and you can always incorporate a stop-off in Milwaukee’s city center – parking in the outskirts and commuting in.

  • Distance from Chicago: 2 hours
  • How to get there: By car

6. Illinois Beach State Park, IL

Day Trips from Chicago Illinois Beach State Park IL

If you want beaches, Illinois Beach State Park is the place to be on a Chicago day trip. The park covers over 4,000 acres, with a beautiful shore path and network of hiking trails. It is an ideal place for a beach day along the shores of Lake Michigan. However, Illinois Beach State Park is equally more than just a beach destination.

It has campgrounds and playgrounds, plus shower blocks and a nature center. Illinois Beach State Park is somewhere to spend an entire day. Start with a hike and visit the nature center before heading to Isherwood Beach, and even camping overnight if your schedule allows it.

The park is quite close to Chicago, taking less than an hour to reach by car. It’s a great day trip if you have a warm day or fancy a beach trip. Or it is the perfect adventure if you fancy camping a night to break up your classic city break.

  • Distance from Chicago: 1 hour

7. Lake Geneva, WI

Day Trips from Chicago Lake Geneva WI

Lake Geneva is a beautiful resort city along the banks of Geneva Lake in Wisconsin, northwest of Chicago. As a small city out of the leading public transport lines, it is best reached by car.

Once you arrive, you are greeted by Gilded Age mansions with dramatic architecture and a scenic Shore Path that snakes around the city’s section of Geneva Lake. Historically, Lake Geneva was used as a bolt-hole for affluent Chicago residents, and looking at the city’s surrounding natural beauty, it’s easy to see why.

Admire Victorian history and Gilded Age architecture, and visit the Lake Geneva beaches. Big Foot Beach State Park has brilliant beaches, especially for a lazy afternoon. Lake Geneva is a beautiful day trip destination to unwind before revisiting Chicago’s chaotic sightseeing scene.

8. Rockford, IL

Day Trips from Chicago Rockford IL

Rockford is a major city located on the banks of the Mississippi River, giving it the nickname’ River City’. Rockford is also called the ‘Forest City’ because of its history of tree felling, forests, and furniture-making industries. It is a shapeshifter with a long history and a prominent place in Illinois’ society. Nowadays, though, it is an ideal day trip candidate and is full of popular attractions and historic places. You can stop by the koi-filled ponds at Anderson Japanese Gardens, kick back in numerous public parks, or head to the Rockford Art Museum. Tinker Swiss Cottage Museum and Gardens is also brilliant.

Rockford is located in northern Illinois, right under the Wisconsin border. We’d recommend combining it with a trip to Madison, located roughly an hour above the city. It is a great stop-off point for those driving to the Wisconsin capital.

9. Indiana Dunes National Park, IN

Day Trips from Chicago Indiana Dunes National Park IN

Forget state parks if you like natural beauty – aim big with Indiana Dunes National Park. This stunning park is far more than just sand dunes and covers 15 miles of beautiful shoreline perfect for swimming and sunbathing. Indiana Dunes National Park is also a hot spot for bird watching and hiking. The national park is located on the southern end of Lake Michigan. It is a beautiful spot to visit to embrace the lake’s beauty. An entrance ticket costs around $20, and you can spend the whole day exploring the park.

Indiana Dunes National Park is located just southeast of Chicago and is ideally combined with visits to South Bend or day trips into Michigan or Indiana.

  • Distance from Chicago: 50 minutes

10. Lakeshore State Park, WI

Day Trips from Chicago Lakeshore State Park WI

Everyone loves an urban park. This stunning park sits just off Milwaukee’s coastline. Still, we will include it as a standalone attraction since it justifies a visit on its own merit. Lakeshore State Park is best explored on foot by walking the Hank Aaron State Trail. You can enjoy city skyline views and expansive vistas over Lake Michigan. And if you are looking for a romantic day trip from Chicago, head to Lakeshore State Park at sunset with a picnic.

The state park is obviously well combined with a visit to Milwaukee. This little island state park is a beautiful spot near the city. It is located off the Historic Third Ward and accessible by a pedestrianized bridge connecting it to the mainland.

11. Monroe, WI

chicago day trips by train

Monroe is pretty cool. The quirky city is known as the Swiss cheese capital. It has a vast history of dairy farming that has given it a massive cheese reputation. You can visit to take food tours – highly recommended – and try local products and produce. You should visit the National Historic Cheese Making Center Museum and the Chalet Cheese Cooperative. There’s also beautiful architecture and historic places, like the Green County Courthouse, completed in 1891. The Monroe Historic Square is in the city’s center, surrounded by shops and aesthetic scenery.

Monroe is a tiny city compared to some of Chicago’s neighboring giants. It is roughly located halfway between Madison and Rockford. It is definitely best accessed by car.

12. St. Joseph, MI

Day Trips from Chicago St Joseph MI

St Joseph is a scenic coastal city in southwest Michigan and an ideal day trip if you want to venture into MI on a day trip from Chicago. It sits along the shore of Lake Michigan with beautiful attractions like Silver Beach County Park and Lions Park Beach. Silver Beach is particularly cute to visit, with a 1910 carousel and restored pavilion that bring a wonderful, vintage-style aesthetic to the city. A classic red and white lighthouse is near the city’s North Pier.

St Joseph is a beautiful choice if you want one of those traditional seaside day trips. It is only a short drive from Chicago, despite the fact that you’ll be venturing through Indiana and crossing the Michigan border. Hooray for Lake Michigan’s close network of US states. It is fantastic to combine with Indiana Dunes National Park and Michigan City.

  • How to get there: By Car

13. Channahon State Park, IL

Day Trips from Channahon State Park IL

Channahon State Park is an absolute must. The state park sits on some of the most historic Illinois canals, housing a restored lock tender’s house for extra historical value. You can enjoy a network of hiking trails with waterfalls, birds, and historic towpaths to snap photos of. Distance isn’t an issue when visiting inland Illinois; Channahon State Park is less than an hour’s drive from central Chicago. It is a great day trip if you want minimal travel time and an insight into Illinois’ canal history.

You can organize guided tours around Channahon State Park, including canoe trips. The state park is a designated part of the Illinois and Michigan Canal National Heritage Corridor. It is widely hailed as an essential part of the state’s history. It is a nature-given adventure park.

14. Oak Park, IL

Day Trips from chicago Oak Park IL

Oak Park is a beautiful village in the suburbs of Chicago. It really packs a punch beyond pretty architecture for such a small area. Visitors can enjoy attractions like the Frank Lloyd Wright Home and Studio, Ernest Hemingway’s Boyhood Home, the National Historic Landmark of Mills Park and the Oak Park River Forest Museum. Oak Park is a quickfire selection of museums in a tiny area, accessible from central Chicago using public transport. What’s not to love? It is the perfect choice if you want trips from Chicago done easily.

It is so handy to jump on a train and be amongst dozens of museums. Additionally, its Unity Temple was recently designated as a UNESCO World Heritage in 2019. Despite all its existing attractions and offerings, Oak Park is very much up and coming in terms of visitor recognition and value for tourism.

  • Distance from Chicago: 15 to 20 minutes
  • How to get there: By train

Suggested Tour: Private Frank Lloyd Wright Tour from Chicago

15. grand rapids, mi.

Day Trips from chicago Grand Rapids MI

Grand Rapids is another major city – think skyscrapers and a beautiful riverside setting with dramatic bridges. Grand Rapids has plenty of culture, with museums like the Gerald Ford Presidential Museum and Grand Rapids Public Museum. It also has a cool, safe, and walkable downtown district, which includes the Grand Rapids Art Museum, an attraction and initiative that spotlights local artists.

We like to catch a shuttle to Grand Rapids, as it has an illustrious brewery history. In particular, it is known for New Holland Brewing, and you can take guided tasting tours at the local breweries that are still running. Otherwise, driving is quicker, and you can stop off at spots like Indiana Sand Dunes National Park, St Joseph, and South Bend. You hug the lower shoreline of Lake Michigan, which is a long but very scenic drive. Ideally, rotate drivers and have a few different stops en route.

  • Distance from Chicago: 3 to 5 hours
  • How to get there: By car in just under 3 hours or by shuttle in under 4
  • Suggested Tour: Grand Rapids Ghost Tour

16. Windmill Island Gardens, MI

Day Trips from chicago Windmill Island Gardens MI

Chicago might be known as ‘Windy City,’ but check out Windmill Island Gardens. This seasonal park features a 250-year-old windmill in an ode to the city’s Dutch influence. You can take self-guided tours of the park, admire the windmill, and meet guides in traditional Dutch costumes. There’s also a tulip garden, which is stunning in spring.

This is one of the leading day trips from Chicago if you want Dutch heritage, and it is even located outside of a city named Holland. Windmill Island Gardens is located in Michigan, so you’ll be driving the south coast of Lake Michigan, cutting through northern Indiana and across the Michigan border. When it comes to visiting Michigan, distance can be a concern. Is it a long day of driving? Yes. But it is incredibly scenic and a great way to combine several attractions. If you have a few drivers, you won’t have any trouble as you can just rotate driving time.

  • Distance from Chicago: 2.5 hours

17. Galena, IL

Day Trips from chicago Galena IL

Galena is an absolute gem of a charming small town, sitting on the banks of the Galena River with tons of Civil War history. The town was home to the Civil War General Ulysses S. Grant, and his former home is a State Historic Site. Of course, Ulysses S. Grant later became a US president, so his story is immortalized. Galena is a great place to visit if you are interested in politics and history. Its town center is relatively walkable and is full of stories and scenic 19th-century architecture.

Galena is right in the top left corner of Illinois, on the border of Iowa and Wisconsin. It is a fabulous add-on from Rockford or Starved Rock State Park, around 1.5 hours away by car.

  • Distance from Chicago: 2 hours and 45 minutes
  • Suggested Tour: Downtown Galena Food and Drink Tour

18. Michigan City, IN

Day Trips from chicago Michigan City IN

Michigan City is just an hour away and is brilliant, accessible day trip material. If you want an easy trip from Chicago, Michigan City is it. Fancy a drive? You can drive there in an hour, passing Indiana Dunes National Park. Fancy a train ride? You can read or nap and reach the city in less than 2 hours. There’s lots of lakeside culture and history, with multiple lighthouses to admire and the quaint Washington Park Beach.

There’s also period history at the Barker Mansion, which showcases English-inspired decor and furnishings in a 19th-century mansion. Admire the history, have a beach day, or enjoy inner-city shopping at outlet stores. Michigan City offers loads and, at the very least, is a change of scene.

You can easily visit Michigan City; proper day-long trips are low on travel time and high on attractions. And that sums up this lakeside city.

  • Distance from Chicago: 1 to 2 hours
  • How to get there: 1 hour by car or 2 hours by train

19. Peoria, IL

Day Trips from chicago Peoria IL

Peoria is a beautiful city in Illinois. It was primarily established as a port city and trading center thanks to its position on the Illinois River. It is located much further inland in central Illinois. It is just an hour or so further central than Starved Rock State Park – hello, potential combined day trip.

Peoria has beautiful riverside parks, including Peoria Riverfront Park and Liberty Park. There’s also the Riverfront Museum and Peoria Historical Society. It is a lovely place to just walk and explore on foot. And the contrast between hectic Chicago and sedate Peoria is vast, making it a worthwhile day trip.

The city is located southwest of Chicago and is best accessed by car. This way, you can also stop off at Starved Rock State Park on the way.

20. Six Flags Great America, IL

Day Trips from chicago Six Flags Great America IL

What about a day at an amusement park? Six Flags Great America is a chain of amusement parks scattered across the US. And there is one on the outskirts of Chicago, creating the best day trip for fun-loving tourists. The park has water park rides, rollercoasters, and all-round fun entertainment. You can get adrenaline on rides like Sky Striker or the American Eagle. Alternatively, try the sedate, family-friendly rides like the Big Easy Balloons or Cubasco tea cups.

Everyone loves a fun day out. And Six Flags Great America is the perfect day trip to skip sightseeing and escape the city to enjoy some quality ‘fun’ time. It is the ideal place to let your hair down and has an impressive range of rides, making it suitable for adults and children. Six Flags Great America is located north of Chicago, just under the Wisconsin border. Get your tickets in advance here.

  • How to get there: 1 hour by car or 2 hours by train then bus

21. Glacial Park Conservation Area

Day Trips from chicago Glacial Park Conservation Area

Finally, there’s the beautiful Glacial Park Conservation Area. This 3,400-acre reserve is a stunning mix of wetlands and prairie, with glacial kames and ample scenic canoeing or fishing opportunities. It is one of the most photogenic places to experience natural beauty on a day trip from Chicago. You can explore Glacial Park on foot or by water or shake things up and book a horseback riding tour. The park has a grand total of 8 miles of shared-use trails, and you’ll definitely want to bring a camera.

Glacial Park Conservation Area opens from sunrise until sunset all year round. It is ideal if you want to switch from the standard suburban park experience to a bit of rugged, remote nature.

  • Distance from Chicago: 1 hour and 20 minutes

chicago day trips by train

There’s so much to experience on day trips from Chicago – whether that’s Dutch heritage, rich history related to the Civil War, or riding water park rides at Six Flags America. You can embrace small-town charm at Oglesby, natural beauty and natural wonders at Indiana Dunes National Park, or craft beer at a local brewery. Chicago’s location right next to three other state borders means you have lots of diversity when choosing day trips. And the ever-presence of beautiful Lake Michigan means a constant barrage of water sports and beaches. Hopefully, you have at least 5 or 6 day trip choices.

Are you looking for more inspiration? Why not check out our guides on the  best things to do in Wisconsin  and  the best places to visit in Michigan ? We’ve also got notes on the best, most  unique things to do in Northern Michigan  specifically, so check that out if you have time to add a couple of days to the end of your Chicago trip. If you have longer, why not take a 2-3 day excursion from Chicago? It is a brilliant launchpad to discover more of the experiences in the states around Lake Michigan. Chicago’s location is by far its winning quality, and you should take advantage of it when planning day trips and excursions.

Plan your trip to Chicago with these Resources

  • 29 of the Best Things to Do in Chicago
  • Where to stay in Chicago: Best Areas and Hotels
  • Top 10 Hot Spots to Eat in Chicago
  • 23 Cool and Unique Things to do in Milwaukee, Wisconsin

Travel Planning Resources

Looking to book your next trip? Why not use these resources that are tried and tested by yours truly.

Flights: Start planning your trip by finding the best flight deals on Skyscanner

Book your Hotel: Find the best prices on hotels with these two providers. If you are located in Europe use and if you are anywhere else use TripAdvisor

Find Apartment Rentals: You will find the cheapest prices on apartment rentals with VRBO . 

Travel Insurance: Don't leave home without it. Here is what we recommend:

  • Allianz - Occasional Travelers.
  • Medjet - Global air medical transport and travel security.

Need more help planning your trip? Make sure to check out our Resources Page where we highlight all the great companies that we trust when we are traveling.

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  • Maps & Schedules
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Aboard Metra, all tracks lead to fun in the city. But Metra's convenient service and flexible schedules also make us the smart choice to some of the Chicago area's more popular destinations, most within walking distance or a quick bus ride from the train stations. Depending on the season, there are plenty of places to go and Metra can take you there.

We sell a $7 Saturday/Sunday/Holiday Day Pass good for unlimited rides on all Metra lines on a single weekend day. The $10 Weekend Pass, available in the Ventra App only, is good for unlimited rides on all Metra lines all Saturday and Sunday. With Family Fares, you can take children age 11 and under along for free.

DuPage Medical Group Field

815-726-2255 1 Mayor Art Schultz Drive Joliet

Home of the Joliet Slammers Rock Island Line to Joliet

Hollywood Casino

1-800-888-7777 49 W Galena Blvd Aurora, IL 60506 BNSF Line Board at Union Station and ride to the  Aurora Station .

Grand Victoria Casino

847-468-7000 250 S Grove Ave Elgin, IL 60120-6447 Milwaukee District West Line Board at Union Station and ride to the  National Street Station .

1-800-427-7247 151 N. Joliet Street Joliet, IL 60432 Rock Island Line Board at LaSalle Street Station and ride to the  Joliet Station .

Arlington Park Racetrack

847-255-4300 Spend an afternoon at beautiful Arlington Park, considered one of the nation’s top thoroughbred racetracks. Enjoy the excitement and non-stop thrills of horse racing in a family setting. Union Pacific Northwest Line Board at Ogilvie Transportation Center and ride to the  Arlington Park Station .

Ravinia Outdoor Music Festival

847-266-5100 Music under the stars with world-renowned performers of classical, pop, jazz and dance. Call for dates and times. Union Pacific North Line Board at Ogilvie Transportation Center and ride to the  Ravinia Park Station .

Brookfield Zoo

708-485-0263 Known for beautifully recreated natural exhibits where a variety of species cohabit as they do in the wild. BNSF Board at Union Station and ride to the  Hollywood Station .

Museum of Science and Industry

773-684-1414 Just south of the Loop area, this magnificent museum has hands-on exhibits for the whole family including a 727 Airplane, the U505 Submarine, a space exhibit, a coal mine tour, a virtual reality exhibit, a giant heart and brain, and more. Metra Electric Line Board at Millennium or Van Buren Street Station and ride to the  57th Street Station ; walk two blocks east.

The Nathan Manilow Sculpture Park at Governors State University

708-534-4486 Encounter major works by masters of contemporary sculpture at the Nathan Manilow Sculpture Park. Established in 1978, the park has grown into a major collection of 26 works that is set within the wild prairie swales of the Governors State University campus. Located just 34 miles south of downtown Chicago, the park is easily accessible aboard  Metra Electric  to the  University Park station . The park is less than a mile walk from the Metra Station, and shuttle service is also available to Governors State University on  Pace bus 367 .

DuPage Children’s Museum

630-637-8000 The DuPage Children’s Museum is a unique discovery center where children and adults learn and play together. BNSF  

Board at Union Station and ride to the  Naperville Station .

Six Flags Great America

847-249-4636 The Midwest’s most exciting theme park with heart pounding thrill rides, exciting shows and many other attractions. Open May - October. Call for dates and times. Union Pacific North Line  

Board at Ogilvie Transportation Center and ride to the  Waukegan Station .

  • Walk south up the hill about one block to Washington Street. Turn right, walk west on Washington Street one block to Sheridan Road.
  • At the NE corner of Washington Street and Sheridan Road, board either Pace Bus Rte.  572  or Rte.  565 .

Elmhurst Art Museum

630-834-0202 The Museum's award winning architectural structure incorporates the Ludwig Mies van der Rohe-designed McCormick House and contains museum galleries, an education center and a variety of outdoor sculpture. Located in beautiful Wilder Park with picnic and playground facilities, it is only one block south of Metra's Elmhurst Station. Union Pacific West Line Board at Ogilvie Transportation Center and ride to the  Elmhurst Station .

Chicago Botanic Garden

847-835-5440 Discover nine enchanted islands surrounded by water and wonder, with breathtaking gardens to explore, lakes and bridges to cross, and a waterfall garden to climb! There’s even a special train garden for families to enjoy in spring, summer and fall. Tram tours, summer evenings with live music, outdoor dining and sunsets could all be found at the Chicago Botanic Garden. Union Pacific North Line Board at Ogilvie Transportation Center and ride to the  Braeside Station  where you can walk west on Lake Cook Road approximately 1 mile to the Gardens. On Sundays during summer months, you can travel to Metra’s  Glencoe Station , then hop aboard the  Garden trolley .

Metropolis Ballroom

847-870-8787 ON STAGE at Metropolis Ballroom Of Arlington Heights, Overlooking Harmony Park - Where every event is an opportunity to meet the artist in person! Union Pacific Northwest Board at Ogilvie Transportation Center to the  Arlington Heights Station ; Walk two blocks south.

Metropolis Performing Arts Centre

847-577-2121 From theatre and music to comedic acts, dance ensembles, children's shows and a cool music series, Metropolis Performing Arts Centre has something for every member of the family. Union Pacific Northwest Board at Ogilvie Transportation Center to the  Arlington Heights Station ; Walk two blocks south.

Frank Lloyd Wright Preservation Trust

708-848-1500 See the world’s largest collection of Frank Lloyd Wright structures...and take a self-guided walking tour of historic Oak Park. Also visit Hemingway’s birthplace and museum . Union Pacific West Line Board at Ogilvie Transportation Center and ride to the  Oak Park Station .

SciTech Hands on Museum

630-859-3434 An interactive science and technology center with over 200 hands-on exhibits on weather, light and color heat, mathematics, sound and music, and magnets and electricity. BNSF Board at Union Station and ride to the  Aurora Station .

Tinley Park Convention Center

708-342-5485 Connected to Metra’s Rock Island Line at the downtown  Tinley Park Station  on Oak Park Avenue via  Pace bus #386 , the Tinley Park Convention Center is known for its contemporary atmosphere and state of the art space, making it a preferred venue for major conventions, trade shows, meetings, and special events of all kind. Rock Island Line

Fashion Outlets Chicago

847-928-7500 Chicagoland’s newest designer shopping mecca! Located about two blocks from Metra’s Rosemont Station (NCS), you can design your shopping excursion around Metra’s convenient, comfortable service. Weekday service only. Take the  North Central Service (NCS)  to the  Rosemont Station

Premium Outlets Chicago

630-585-2200 Metra’s BNSF line offers fast, reliable and economical travel to Aurora where you can connect with  Pace bus #533  directly to Premium Outlets in Aurora, where you’ll “shop brilliantly” for designer brands at discount prices. Take the  BNSF  to the  Aurora Station .

Kohl Children's Museum

847-832-6600 The Museum is served by the North Glenview Station on the Metra Milwaukee North Line. From the station, walk 1/2 mile east on West Lake Avenue to Patriot Boulevard.

Milwaukee North Line Schedule

Let's Roam Explorer

The 25 Best Day Trips from Chicago for Every Style of Adventure

Whether you’re looking to escape your hometown or planning a trip to the Windy City and seeking some detours, try any one of these day trips from Chicago!

chicago day trips by train

Chicago Illinois is one of America’s great cities. It is also perfectly situated for exploring. Home to the world’s first skyscrapers, Chicago is the third-largest city in the United States, and rather surprisingly so, as it seems to rise out of nowhere, from the middle of the cornfields. The city buts up against vast Lake Michigan and is home to the Cubs, The White Sox, and ‘Da’ Bears, and has the “world’s largest free-admission food festival:” The Taste of Chicago . It also happens to be home to the world’s best pizza (sorry New York). Chicago is an awesome city to explore, but nature lovers, and those looking to escape the city life, will find no shortage of great day trips from Chicago!

If the Windy City is your home, or you have spent a few days exploring, and you are ready to head for less hectic surroundings, Chicago is also perfectly situated for great day trips and weekend getaways. In this guide, we will show you some of the best day trips from Chicago to catch your breath and slow down a bit. Within a three-hour drive from Chicago, you can find wineries, amusement parks, charming Dutch towns, and beautiful state parks, a trip for every kind of adventurer!

Scavenger Hunts in Chicagoland

Before you head out to the surrounding areas, let us take you on a proper tour of the Windy City, with our Chicago Loop Scavenger Hunt . This app-led adventure will take you through the heart of Chicago on a journey filled with photo and trivia challenges meant to rack the brain and cause intense laughter. Our hunts are informative and tons of fun!

25 Day Trips From Chicago

Disclaimer: The distances and time recorded in this guide were taken from Google Maps at the time of writing. They are driving distances from Downtown Chicago. They may vary drastically depending on what day and time you choose to make your trip. We advise that you double-check the timing while planning your day. Also, bear in mind that many of these destinations can be reached by train or metro and may be faster that way!

1. Rockford

​Distance: 95 miles

Travel Time: 1 hr 40 mins

Rockford is a great day trip from Chicago for those with kids on board. Head straight for Discovery Center Museum , and let your kids dive into more than 300 interactive exhibits. They will playfully learn about air and flight, agriculture, their own bodies, and even the science behind color, light, and electricity. The museum is part of the great Riverfront Museum Park Campus. So, you can very easily make a full day (or two) without even leaving the park. Stop next door at the Rockford Art Museum, and then head to the Burpee Museum of Natural History(they have a baby T-rex.) 

Once you’ve had your fill of artifacts and art, the Anderson Japanese Gardens offer some much-needed fresh air. The gardens cover 12 acres and are filled with beautiful koi ponds and walking paths through the well-manicured flower and botanical gardens. The gardens are actually on the private property of businessman, John Anderson. After visiting the Japanese gardens in Portland, he fell in love with the zen and brought it home to his very wet backyard in Rockford. 

If you prefer your plants tropical, then head for the 11,000 acres of Nicholas Conservatory . Rock Cut State Park is a great place for a picnic or to stretch your legs on the lovely trails. Rockford also has a distinctly Swedish history on display at the Erlander House Museum. You can also try out traditional Swedish food at the Stockholm Inn . From exploring the land of ancient dinosaurs to chowing down on Swedish meatballs, Rockford Illinois is the perfect day trip from Chicago for families.

2. Chicago Botanic Garden

Distance: 25 miles

Travel Time: 43 mins

The Chicago Botanic Garden is in the suburb of Glencoe, just north of the city. Not only does the garden boast over 385 acres of natural beauty. They also have fun programs throughout the year to entertain your crew. The model railroad is interesting and displays scale models of several popular American landmarks. Make sure to download the Model Railroad BINGO game before you go. 

From November to January, The Chicago Botanic Gardens are transformed into one of the most impressive Christmas light installations in the Midwest. It’s so much more than Christmas lights, with a cacophony of light art installations falling from the sky and popping up from the earth. Traversing the gardens during the holidays is nothing short of magical! Tickets sell out very fast though, so make sure to book early.

The gardens are a quick trip from Downtown Chicago and the perfect place to get away from the city for a little nature break.

3. Oak Park 

Distance: 9 miles

Travel Time: 22 mins

Oak Park is a suburb just east of Downtown Chicago. The city prides itself on diversity in every walk of life. So, it is an eclectic city, where everyone, and every way of thought, are not only accepted but treasured! It also happens to be the perfect day trip for architecture lovers. Oak Park was the home to the famous Frank Lloyd Wright Home and Studio and showcases his own home, plus several more of his perfectly designed houses. Guided tours can be booked through the Frank Lloyd Wright Trust . You can also do a walking tour through Wright District, just make sure to see the incredible Unity Temple, a church Wright designed that is stunning and unexpected, in that FLW kind of way. 

4. Brookfield Zoo

Distance: 17 miles

Travel Time: 29 mins

The iconic Brookfield Zoo has been entertaining and educating families since 1934. The zoo covers 216 acres of natural animal habitats that are home to more than 2,000 animals. Visit the new baby wallabies, see the dolphin show, or get up close and personal to the resident Polar Bear. Travel to the Savannah to meet giraffes, rhinos, and zebras, before heading for Tropic World and coming face to face with a giant gorilla. Brookfield is a leader in conservation and animal care, as well as public and advanced zoological education. If you are unable to visit, send them a donation instead. They are doing some great work!

5. Springfield, Illinois

Distance: 218 miles

Travel Time: 3 hrs

Okay, Springfield is pretty far for a day trip, definitely pushing the boundary, but it can be done if you leave early. Springfield is a great destination if you are interested in history. It’s Illinois’ capital city and home to the beautiful Old State Capitol building. The old girl is a Greek-Revival masterpiece that is full of history. Honest Abe gave his famous “House Divided” speech from here, and he also lay in state here for a couple of days after his 1865 assassination. 

Visitors can tour the Capitol on their own or take a 30-minute docent-guided tour. The grounds also host several special events throughout the year including Civil War Encampments and Holocaust Remembrance Day. 

While in Springfield, you can also tour Lincoln Home , a national park celebrating the life and legacy of the 16th president. It was the only home ever owned by President Lincoln and the docents here do a great job walking you through his life from rural Kentucky to the White House. After that, you might as well stay on the Lincoln train and head for the Abraham Lincoln Presidential Library and Museum . You will be a bonafide Lincoln expert by the end of the day!

For a little fresh air, head over to the trails at the Adams Wildlife Sanctuary . This urban park is 40 acres of trails and woodlands, right in the center of Springfield. The estate belonged to long-time Springfield natives, the Adam’s Family (not the creepy ones). The home was built in 1869 and inhabited by the family until the death of Miss Margery Adams in 1983. It’s quite an oasis and definitely worth a stop. 

Truthfully, Springfield is much better suited to a weekend getaway or more. In addition to what we already detailed, the city also offers modern government sites like the Ilinois Governor’s mansion. It’s the home of the 1908 Race Riot Walking Tour, The Air Combat Museum, and The Camp Butler National Cemetary. There are plenty of great restaurants and breweries to explore too!

6. Kalamazoo, Michigan

Distance: 146 miles

Travel Time: 2 hrs 15 mins

Kalamazoo is loaded with fun activities. Gilmore Car Museum has a huge collection of vintage and antique cars. Actually, it has one of the top five automobile collections in the US, with more than 300 fully-restored pieces including rare Studebakers and Model A’s. The museum covers 90 acres and is a must-see for car and motorcycle lovers. 

The Air Zoo Aerospace and Science Museum is a blast. See a replica of the Wright Flyer, WWII Hellcats, and the final remaining Blackbird Stealth Plane. The museum also has a spacecraft wing with a 1970s replica command module and shuttle. The kids will love the interactive exhibits and flight simulators. 

Other things to do in Kalamazoo: (yes, Kalamazoo is the funnest word ever, and it is very hard to refrain from over-rhyming) Anway, visit the Kalamazoo Nature Center with its forest footpaths and butterfly gardens, and the oldest brewery in Michigan, Bell’s Brewery . While you certainly can’t cover all of Kalamazoo in a day, you can see a lot. It’s one of the best city getaways from Chicago.

7. Skokie, Illinois

Distance: 15 miles

Travel Time: 23 mins

Skokie is home to The Illinois Holocaust Museum , the second-largest Holocaust museum in the United States. It covers over 65,000 square feet, all dedicated to the horrors of the Holocaust and the memories of the survivors. The museum is a labor of love from the Chicago area Holocaust survivors. They opened the tiny, store-front memorial, in Skokie, in the 1970s, when the city was being threatened with neo-nazi marches and parades. In 2009, they scored a major upgrade to the new, modern museum, and it is definitely worth a visit!

Just in case a trip to Italy isn’t in your near future, no worries, Skokie also randomly has a half-sized replica of The Leaning Tower of Pisa known as “The Leaning Tower of Niles.” The Skokie Northshore Sculpture Park is also the perfect place for a picnic and a stroll!

8. Evanston, Illinois

Distance: 14 miles

Travel Time: 37 mins

If you are looking for a true day trip, Evanston is an easy jot north of Chicago. We recommend starting at the Baha’i House of Worship , which is actually a bit north of Evanston, in Wilmette. The architecture is out of this world. It’s unique and extremely beautiful! 

Evanston also has some quirky museums. The Block Museum of Art is located on the camp of Northwestern University. It’s an outdoor sculpture museum showcasing 16 works of art. Take a walking tour for something free to do in Evanston. The Halim Time and Glass Museum has an incredible collection of stained glass, as well as clocks from around the globe. The American Toby Jug Museum has the largest collection of its kind in the world, with over 8,000 Toby jugs (Philpots) and character jugs. Evanston also contains several small house museums detailing the history and culture of the area. It’s the perfect day trip for the art and history lover!

9. Lake Geneva, Wisconsin

​Distance: 83 miles

Travel Time: 1 hr 30 mins

Lake Geneva is a resort lovers paradise. It has long been a haven for wealthy Chicago families. If you want to spend your day sipping cocktails and gazing at the natural beauty of Geneva Lake, then there is no shortage of fancy resorts to choose from. 

However, you don’t need to be super wealthy or even step foot on a resort to enjoy Geneva Lake. Outdoor sports are king here too. Rent a paddleboard or kayak to cruise the lake or stroll around Lake Shore Path, where you can admire the incredible mansions. The 26-mile trail was once a Native American path used to travel between several Potawatomi Tribal villages. The trail was later used by migrant workers, and finally, after The Great Chicago Fire of 1871, several wealthy families escaped the city and built their new summer palaces on the shores of Geneva Lake. 

You can now stroll the path with the beauties of nature on one side and man-made beauty on the other. The mansions are inhabited, so please stay on the trail and be respectful of private property. Once you are done strolling, take a dip in the cool waters and relax in the sun on Riviera Beach. Lake Geneva is the perfect day trip from Chicago for water lovers and those who just want a relaxing day outside!

10. Morton Arboretum

Distance: 26 miles

Just west of Downtown Chicago, in the suburb of Lisle, the Morton Arboretum where you can learn everything ever wanted to know about trees. These guys are a little obsessed, in the best way! The arboretum is exceptional in the fall when the leaves are changing colors, but they also have special events year-round for adults and children, including marathons, holiday light installations, and whiskey dinners. The park offers a guided tram tour that is well worth your time as well. There are over 16 miles of trails to explore and a Children’s Garden where kids can splash in the streams and climb and slide on nature-themed exhibits made just for them! It’s beautiful. It’s fun, and it’s a great relaxing day away from the city. 

11. Michigan City, Indiana

Distance: 60 miles

Travel Time: 1 hr 5 mins

Michigan City lies on the southern border of Lake Michigan. The Century of Progress Historic Homes is a collection of buildings from the 1933 Chicago World’s Fair that was moved by barge to Beverly Shores. Once a year the buildings are open for tours in conjunction with the National Parks Service. The houses are incredibly modern-looking and must have been a sensation in 1933. Four of the houses are inhabited by sub-leasers who worked in conjunction with the park service to renovate and preserve the homes.

Move on to the Old Lighthouse Musem , the oldest lighthouse in Indiana, or stroll around the Washington Park Zoo . Michigan City has some great breweries to explore as well, but its real claim to fame (and the reason it makes this list) is Indiana Dunes National Park . This park is beautiful with over 50 miles of trails and 15 miles of shoreline. It used to be called the Indiana Dunes National Lakeshore, and the wide swaths of beach, flanked by towers of sand are still certainly the main attraction. The state park of the same name is right next door, and it showcases the three tallest sand dunes. Bird-watching is a favorite past-time here, along with horseback riding in the summer and snowshoeing in the winter. Kayaking or fishing on the lake is also a great way to spend a few hours! 

12. Holland, Michigan

Distance: 151 miles

Travel Time: 2 hrs 20 mins

Holland is in one word … adorable! Dutch, Calvinist settlers arrived in the region, in the mid-1800s. They built a village resembling their homeland, and Holland is still the go-to place to experience Dutch culture in the area. There is even a tulip garden, how very Dutch! Veldheer Tulip Gardens has over 5 million tulips. We would suggest visiting Holland in the spring so that you get to experience the flowering! 

Several restaurants and breweries around town offer traditional foods from the Netherlands, and when you feel sufficiently fat, head for Windmill Island Gardens , because no Dutch town would be complete without some windmills. The center-piece mill is over 250 years old and was transported to the area in the 1960s. For a bit of the international in a day trip from Chicago, you can’t beat a visit to Holland!

13. Starved Rock State Park, Oglesby Illinois

Distance: 93 miles

Starved Rock State Park is just outside the city of Oglesby. It is the go-to hiking location for Chicagoland. The beautiful park includes strange rock formations, that are unexpected in the Illinois flatlands, and over 13 miles of hiking trails along the Illinois River. The park is beautiful year-round. In the spring, all the waterfalls are at peak flow, tumbling over the walls of the 18 canyons in the park. A visit in the autumn will treat you to all the fall-foliage color changes. 

While you are in the area, be sure to check out Matthiessen State Park as well. It is only 3 miles away from the more popular (and crowded) Starved Rock State Park , and as you would imagine, it has all the same beautiful waterfalls and forested trails.

Nearby, at the Vermillion River, adventurers can enjoy some of the best river rafting in the region. The river has 14 rapids, mostly Class 1 and II, so it’s manageable for families, even with young kids. The Starved Rock Lodge is a great place to catch lunch or dinner, or should you decide to stay the night, you can snag a beautiful room. For nature lovers and adventurers, you really can’t beat a day trip to Oglesby. 

14. South Haven, Michigan

Distance: 123 miles

Travel Time: 1 hr 56 mins

South Haven is one of the best small towns on Lake Michigan. It is the home of the Michigan Maritime Museum The museum has permanent and rotating exhibits, highlighting Michigan’s maritime history and shipwrecks, but the favorite is the interactive Friends Good Will . It is a replica of an 1810 Top-Sail Sloop that is available for sailing tours. Guests can take a cruise on the replica tall ship, just like a sailor in the War of 1812. While the old girl is a bit creaky, it’s a pretty cool experience. 

Other than the museum, South Haven also offers some great outdoor activities. Bikers will love the over 30-mile Kal-Haven Trail, which links South Haven to Kalamazoo. Bikes can be rented from several shops in town. Van Buren State Park offers beautiful Lake Michigan beaches to lounge on too. If you happen to be in town during August, you can celebrate with the locals at the Blueberry Festival . The town comes alive with live music, pie-eating contests, a 5K, and all other-manner of blueberry-themed events. 

15. Galena, Illinois

Distance: 164 miles

Travel Time: 2 hrs 40 mins

Galena is a great day trip destination for history buffs. Galena was home to General Ulysses S. Grant and his family and features several prominent historic sites. Grant had actually ended his military service by the time he moved to Galena in 1860 and was working as a store clerk, but when the Civil War broke out, he was called back into action. The Ulysses S. Grant Home was presented to the war hero upon his return in 1865 by the citizens of Galena. He lived there until taking his spot in the White House years later. 

For more Grant-centered info, head to Galena & U.S. Grant Museum . It explores the history of Galena, including exhibits on blacksmithing, leatherworking, and lead mining. Both the Gran Home and the museum are housed in beautiful, red-brick Italianate villas. Speaking of Italianate mansion, consider spending the afternoon at the Belvedere Mansion and Gardens !

For the paranormal folks out there, Galena also happens to have several haunted locations. Join a ghost tour for an evening of spooky fun!

16. Fairbury, Illinois

Distance: 107 miles

Travel Time: 1 hr 45 mins

Fairbury is a road trip for the foodies. Fairbury is the location of two farm-to-table sites that service restaurants all over Chicago. Kilgus Farmstead is a dairy farm offering 1-hour tours detailing the milking process and the making of homemade ice cream, complete with samples! Slagel Family Farms specializes in hormone-free, farm-raised meats. They also offer interactive tours, complete with butchering demonstrations, followed up by a full farm-fresh dinner. The dinners take place in their charming barn, and make for a perfect date night! Make sure to stop by each farms’ grocery store to stock up on fresh eggs and other local goodies from nearby farms.  

17. Monroe, Wisconsin

Distance: 137 miles

Travel Time: 2 hrs 12 mins

Our second foodie location is the village of Monroe. Monroe is in the middle of cheesemaker territory! Learn all the ins and outs of the cheese industry at the National Historic Cheesemaking Center , then head for Alp and Dell where you can find more cheese varieties than you ever imagined. They are almost all local, and the staff there are experts. They can help you make wine and beer pairings like a pro. Take a walking tour of the town and visit cute Courthouse Square. The Green County Courthouse is on the National Registry of Historic Places and has lovely Romanesque architecture. Take the interactive tour and have your picture made in a judges gown and gavel!

If you want to spend a bit of time outside, hike part of The Badger Trail, a 40-mile journey that links to Madison. It traverses several small towns, wooded areas, and old tunnels, and it’s the perfect way to spend an afternoon outdoors. 

18. Peoria, Illinois

Distance: 128 miles

Travel Time: 2 hrs 28 mins

Peoria has had a huge revitalization over the last few decades. The old Warehouse District is now a conglomerate of unique art galleries, funky boutiques, and yummy eateries. The Riverfront District has seen even more gentrification and is full of breweries, museums, and even a really great farmer’s market on the weekends. Peoria seems to always be having a festival by the water, and when they aren’t, you can take a ride on a historic riverboat. 

Wildlife Prairie Park is located just outside Peoria. It consists of 1800 acres and is home to over 150 animals. The park has its own tourist train and a safari bus, so you have two choices for tours. You can make a full day of the park. Encounter the animals. Hike or bike the miles of trails, play disc golf or go visit the lakes.

Whether you are a shopper, a group of friends looking for a unique night out, or a nature lover, Peoria is a great day trip for you!

19. Milwaukee, Wisconsin

Distance: 86 miles

Travel Time: 1 hr 25 mins

The little city of Milwaukee on the shores of Lake Michigan has made quite a name for itself. It is famous for Summerfest Music Festival . The Milwaukee fest has been rocking for over 50 years and plenty of Country Music and Rock and Roll Hall of Famers have graced the stage there. With 11 stages rocking at once, it is a pretty epic show. 

The Milwaukee Art Museum has a stunning collection and is housed in a seriously innovative building. Many families argue that the Betty Brinn Children’s Museum is one of the best in the USA. Betty Brinn spent her childhood in foster homes and orphanages, so her rise to a successful place in the Milwaukee business world was an impressive one. She spent her life advocating for disadvantaged women and children, and the museum is her legacy.

Milwaukee is home to legendary beer maker, the Pabst Brewing Company. The Pabst Mansion is now on the National Register of Historic Places and offers guided tours. It’s a monster. The huge Harley-Davidson Museum is a top tourist attraction as well. 

Honestly, we would recommend that you give Milwaukee a full weekend unless you just want to visit one or two specific sites. It’s a great city, and there is a lot to see!

20. Grand Rapids, Michigan

Distance: 179 miles

Travel Time: 2 hrs 45 mins

Grand Rapids is the premier location for beer lovers. The city is loaded with great microbreweries. Grand Rapids is also home to some great museums, including the Gerald R. Ford Presidential Museum, the Grand Rapids Art Museum, and the Grand Rapids Children’s Museum. 

If you happen to be in town during ArtPrize, then lucky you. The annual event wraps the city in new and innovative art. It’s an outdoor/indoor art competition usually lasting 18 days. Artists create works that are displayed in galleries, museums, public parks, and even restaurants and bars. The whole city is transformed, and it is definitely worth seeing if you are in the area1 

Our ultimate guide to “ The Best Things to Do in Grand Rapids ” will give you more great ideas should you decide to stay a little longer in Grand Rapids.  

21. Explore the Sunflower Fields

Distance: 41 miles to Johnson’s (Other farms vary.)

Travel Time: 47 mins to Johnson’s (Other farms vary.)

From early July to late September, the fields surrounding Chicago are ripe with happy Sunflowers. The yellow beauties are not only soothing to the soul, but they are the perfect day trip for photographers. Whether you are a landscape photographer, you need a perfect family photo, or you just want a color Instagram selfie, the flower fields are for you! There are many private farms with varying degrees of availability, but one of the biggest and best is Johnson’s Farm. Not only do they have over 20 acres of sunflowers, but you are also allowed to pick them! They also offer a Fun Farm for children complete with an obstacle course, pedal karts, train and tram rides, a goat farm, and a jump pad. It’s a full day of fun!

Each farm has different rules about photography. Some require you to book an appointment in advance and pay a photographer’s fee if you plan on bringing professional camera equipment. 

22. Fennville, Michigan

Distance: 141.3 mi

Travel Time: 2 hrs 15 min

Fennville is in Michigan’s fruit belt. Chicagoans flock in droves to the country to pick peaches, cherries, and apples, depending on the season. Fennville is our favorite town to make a home base. Crane Orchards is popular for U-pick tours, and the hard ciders at Virtue Farms are top-notch. They supply many of the local restaurants in town with fresh goodies, but you can also sip a cider right on their beautiful property. Featherstone Antique Mall is a great place to peruse for treasures. There is no better pie than what you will find at Crane’s Pie Pantry . Plus the adorable restaurant/bakery/winery is located in the most charming centuries-old barn! It’s lovely. 

In June, you can enjoy the Fenn Valley Wine Festival , a celebration of live music and local wines. No matter what you do in Fennville, end your day at Salt of the Earth , everyone’s favorite farm-to-table local eatery.

23. Southbend, Indiana

Distance: 96 miles

Travel Time: 1 hr 35 mins

Home to the Notre Dame Fighting Irish, Southbend India is a pretty typical Midwestern city. There is a great History Museum housed in a lovely Victorian Mansion, and the city has a wonderful farmer’s market, but Notre Dame really runs the show here. The student population is 20,000 strong and the campus is beautiful. Take a tour of the campus noting the gold dome of the Main Building, the Basilica of the Sacred Heart , and the Grotto of Our Lady of Lourdes . The University of Notre Dame is older than the city of Southbend, itself, and tradition runs deep! It’s the perfect day trip for football lovers!

24. Madison, Wisconsin

​Distance: 147 miles

Flanked by lakes, Madison is the capital of Wisconsin and a long but good day trip from Chicago. Madison is another university city, so the vibe is young and fresh. History lovers, start with a tour of the Wisconsin State Capitol building. Not only do you learn a little about the city and see some beautiful architecture, but you will also walk through one of the best farmer’s markets in the region, so come hungry! It’s open every Saturday from April to November.

The farmers’ market isn’t the only place to get good food, though, Madison is loaded with fancy cheeses and craft beers. One of the local favorites is the Malt House . The dive has been serving up brew since the Civil War years and has plenty of local goldens on tap. For those fancy cheese lovers, head to Fromagination , where you can sample artisanal cheese and learn all about pairings from the cheesemongers. 

Biking is a big thing in Madison, and their local BCycle stations allow you to rent a bike for 30 minutes segments and explore the trails around Lake Monona. We also highly recommend a stroll through the Olbrich Botanical Gardens !

Tired and ready for a beer? Try our Madison Bar Crawl Scavenger Hunt and find all the best brews!

25. Gurnee, Illinois

Distance: 44 miles

Travel Time: 45 mins

Gurnee is a getaway for shoppers! Gurnee Mills is a huge shopping complex with over 150 stores. Whatever it is you need, you can find it here. If you hate shopping, no worries. Gurnee is famous a popular destination for one other reason— Six Flags Great America . The giant amusement park is full of traditional coasters and waterslides and wave pools at Hurricane Harbor Water Park.

For thrills seekers, shoppers, and families, Gurnee Mills is the perfect Chicago day trip!

Closing Thoughts

Chicago Illinois is a thriving city with plenty of action, but within just a few hours of the chaos, you can explore quiet state parks, wander lush sunflower fields, learn Civil War history, and enjoy the fruit of the vine. We hope you found your next day trip idea here. Use the comment section to let us know where you’re going!

For more vacation ideas, check out our guide to the best day trips from Boston ! And keep your eyes on our travel blog for more tips and travel ideas.

Frequently Asked Questions

There are several great day trips from Chicago ! The city is perfectly situated to visit small towns around Lake Michigan. Popular choices include Grand Rapids, Madison, and Milwaukee.

Start with a scavenger hunt of the city , then take a day trip from Chicago to the Dutch village of Holland, tour Notre Dame in Southbend, or spot wildlife in Peoria.

The windy city is surrounded by rural areas, perfect for hiking, kayaking, and exploring. That means there are some fantastic day trips from Chicago , like Starved Rock State Park and the Indiana Dunes.

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The 7 best day trips from Chicago

Karla Zimmerman

Dec 11, 2023 • 6 min read

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Indiana Dunes, one of the country's newest national parks, is easily accessible on a day trip from Chicago © Jon Lauriat / Getty Images

Chicago has enough cloud-poking towers, rockin’ live-music clubs and world-class museums to keep you occupied for weeks. But just beyond city limits, you can also scale sand dunes at a national park, rev a Harley and amble around wineries.

Here are seven easy day trips that are no more than two hours away from the Windy City .

Sunset on the shore of Lake Michigan in the Indiana Dunes National Park.

1. Get into nature at Indiana Dunes National Park

Travel time: 1 hour, 30 minutes

Rustling grasses, bird-filled marshes and white-pine forests fill a whopping stretch of Lake Michigan shoreline at Indiana Dunes National Park , which feels a world away from the big city. Rugged beaches beckon, and sweet hiking trails meander up the sand and through the woodlands.

Try the 3 Dune Challenge, a view-tastic 1.5-mile climb to the park’s highest dunes: Mt Jackson, Mt Holden and Mt Tom (just to confuse you, these are in Indiana Dunes State Park , a pocket within the national park.) Biking, paddling and winter snowshoeing are other fun activities available in the park.

How to get to the Indiana Dunes from Chicago: South Shore Line commuter trains make the 80-minute trip several times daily from downtown Chicago to Dune Park station. By car, the 50-mile trip takes one to two hours, depending on traffic.

A group of Harley-Davison motorcycle riders in Milwaukee, Wisconsin, on a sunny day

2. Admire Harleys and artwork in Milwaukee

Milwaukee  is  Wisconsin 's largest city, and it's a rollicking day trip from Chicago. Stop by the Harley-Davidson Museum to gawk at hundreds of motorcycles, including Elvis’s custom-built hog. Harleys were invented in Milwaukee, hence the big bike love. The Milwaukee Art Museum drops jaws with its kinetic “wing” that soars open and shut, as well as its outsider art and Georgia O’Keeffe paintings.

During baseball season,  Miller Park is the place to be for beers, bratwursts and the oddball sixth-inning foot race between people dressed in giant sausage costumes. Milwaukee has a reputation as a drinker’s paradise, with more bars per capita than anywhere in the US besides New Orleans. Friendly neighborhood taverns pop up on almost every corner.  Champion’s shows the local spirit.

How to get to Milwaukee from Chicago: Amtrak runs seven trains daily to downtown Milwaukee, with a journey time of 90 minutes. By car, take the I-94 for the roughly two-hour trip.

3. Tour the lakeside hamlets of Harbor Country

Harbor Country comprises several lakeside hamlets just over the Michigan border, where Chicagoans retreat for a taste of small-town life. New Buffalo is the most resort-y of the bunch, where you can catch a wave at the public beach and follow it up with suds at the Beer Church .

Three Oaks is a bohemian farm-and-arts village where you can browse Elm Street’s galleries and design shops. Antique stores and folksy delis abound in Union Pier, Lakeside, Harbert and Sawyer. Several wineries, such as Tabor Hill , surround the communities and offer tastings. 

How to get to Harbor Country from Chicago: Harbor Country is a 90-minute drive east from downtown Chicago via I-90 and I-94. While Amtrak stops in New Buffalo, the times aren’t convenient for day trips, and you’ll need your own wheels to access the other towns. 

4. Encounter the thought-provoking Illinois Holocaust Museum

Travel time: 25 minutes

The  Illinois Holocaust Museum is the third-largest Holocaust Museum in the world, after those in Jerusalem and Washington, DC. Besides its haunting Nazi-era rail car and videos of survivors' stories from WWII, the venue contains thought-provoking art about genocides in Armenia, Rwanda, Cambodia and other countries. The special exhibitions are particularly impressive.

How to get to the Illinois Holocaust Museum from Chicago:  By car, take I-94 – the 18-mile trip takes about 25 minutes. On public transportation, take the Union Pacific North (UP-N) train at Ogilvie Transportation Center to Davis Street/Evanston. Catch the 208 bus at the Davis and Maple stop and get off at Golf Rd and Woods Dr. It's a two-minute walk to the museum. The trip takes a little over an hour.

Exterior shot of the Stone Manor on Geneva Lake USA

5. Walk a section of the 21-mile Geneva Lake Shore Path

Old-money Chicagoans fled to Geneva Lake in the late 1800s to escape the urban heat and chill in the true-blue, spring-fed water. It’s still high on the getaway list, and while the mansion-strewn shoreline is sometimes called “the Hamptons of the Midwest,” visitors of more modest means are just as welcome.

Nowhere is this more evident than on the Lake Shore Path, the 21-mile public trail that goes through all water’s-edge properties – right through their front lawns! – for close-up views of the mega estates. Taking a boat ride with Lake Geneva Cruise Line is a must, as is a trip to the old-school Cheese Box for hunks of aged cheddar, havarti and other Wisconsin-made goodness.

How to get to Geneva Lake from Chicago: You need a car for this day trip. Lake Geneva, the main town on Geneva Lake, is 80 miles northwest of Chicago. Take I-94 north to Wisconsin highway 50 west. The trip takes 90 minutes to two hours by car.

6. See the home of modernist architecture in Oak Park

Travel time: 45 minutes

Architect Frank Lloyd Wright lived in the leafy suburb of Oak Park, next door to Chicago, for 20 years. Fans come from all over the world to tour his home and studio where he developed the famous Prairie style, as well as to gawp at his  Unity Temple  – named a UNESCO World Heritage site in 2019 – that’s considered to be the first modern-style building.

Ernest Hemingway is Oak Park’s other famous son. He was born in a sprawling Victorian home just a few blocks from Wright’s pad. It’s now maintained as the Hemingway Birthplace Museum and gives a peek at Papa’s formative years.

How to get to Oak Park from Chicago:  It’s a simple excursion via Chicago’s public transit system. Take the Green Line L train from downtown to Oak Park station, from which everything is within a mile's walk.

Baha’i House of Worship with a pink and blue sky in the background

7. Explore Evanston, one of the top college towns in the US

Travel time: 40 minutes

Evanston is Chicago’s neighbor to the north, a lakefront town of sprawling old houses, artisan shops and bookish cafes where college students caffeinate. Check out the quirky American Toby Jug Museum , with the world’s largest collection of character-shaped jugs (think Barack Obama, Mick Jagger and R2-D2 as ceramic pitchers), and the Baha’i House of Worship , an eye-popping temple surrounded by peaceful gardens.

Both are free, which leaves money in your pocket to rent a sailboat, kayak or stand-up paddleboard at the Northwestern University Sailing Center and get out on glimmering Lake Michigan. Otherwise, wander among the boutiques, brewpubs and brioche-laden bakeries like Hewn that pepper the walkable downtown.

How to get to Evanston from Chicago: Chicago’s L trains go to Evanston. During weekday peak times, take the Purple Line direct from downtown Chicago or take the Red Line to Howard station and switch to the Purple Line. It’s about a 40-minute trip, with departures every 10 minutes or so.

This article was first published September 2019 and updated December 2023

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My Flying Leap

11 Unforgettable Day Trips from Chicago

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Chicago is a wonderful city in the USA worth visiting because of the food scene, nightlife, and architecture. Chicago has so many museums and neighborhoods to explore. Once you’re done touring the city, don’t miss the opportunity to take some day trips from Chicago!

Sometimes the busyness of the city can be overwhelming both for residents and travelers. Taking a day trip (or three!) allows you to breathe some fresh air and see more of the state of Illinois. 

By adding a few extra days to your itinerary, you can spend your time taking a few Chicago day trips. You can also easily visit nearby states like Michigan and Wisconsin since Chicago borders them. 

Here are the top ten day trips from Chicago and what you can expect on each of them.

bright red chicago sign, downtown chicago

This post may contain affiliate links, which means I’ll receive a commission if you purchase through my links at no extra cost to you. Please read the full disclosure for more information.

Visiting Chicago 

Heading to Illinois? Chicago is usually the first stop for most travelers to the state. A weekend in Chicago is enough to see all the best sites, but you can easily spend a few weeks or more. 

After a few days of sightseeing and touring around Chicago, here are the best places to visit near Chicago and what to do in each place:

  • Cycle around Lake Geneva
  • Grab a beer in Milwaukee 
  • Go fruit picking in Fenneville 
  • Visit the small town of Gurnee
  • Go to a tulip festival in Holland, Michigan 
  • See the flowers blooming at Chicago Botanic Gardens 
  • Go horse riding in Indiana Dunes National Lakeshore 
  • Take a guided tour through the Anderson Japanese Gardens
  • See the Discovery Center in Rockford 
  • Go to a festival in Cedarburg 
  • See bison in the Midewin National Tallgrass Prairie

Click the link to go directly to the section below. Or scroll down to read them all!

chicago skyline, park surrounding a highway, tall skyscrapers in the distance

1. Cycle Around Lake Geneva 

Lake Geneva is one of the best day trips to take in the warmer months. It’s a small city on the shore of Geneva, Lake in Wisconsin. The city is a resort town with many hotels, shops, and tourists. 

The Lake Geneva Shore Path is the main attraction. It’s 21 miles long and is perfect for biking and walking. Lake Geneva also offers cruises for those that want to be out on the water. They have daytime and sunset cruises. 

You can easily head back to Chicago in the evening if you want to since the drive is only about an hour and 40 minutes. Before leaving the area, make sure to walk around the city center, where there are some great boutique shops. 

lake geneva shoreline, boats in the water, chicago day trips, chicago road trips, day trips to chicago

Getting to Lake Geneva

Renting a car is the fastest and easiest way to get to Lake Geneva. It takes about an hour and a half when you drive along I-94 W and WI-50 W. There is also an option to take a train, but I don’t recommend it as it includes transfers, and the journey can take up to 3 hours.

2. Grab a Beer in Milwaukee 

If you want to head to another nearby city, you can head up to the state border and be in Wisconsin in about an hour and 35 minutes. 

Milwaukee has plenty of things to do, but beer lovers will love this city the most. Craft breweries can be found all over the city, along with microbreweries. Many of the older breweries have a long history and even offer historical tours. 

Here are the best places not to miss:

  • Lakefront Brewery : Offering seasonal beers with local ingredients, this brewery is one of the most famous in Wisconsin. They have a diverse selection of flavors. Everyone in your group should be able to find something they like, including those who are gluten-free!
  • City Lights : Famous for its coconut beer, City Lights is in a historic building that also offers tours. They have a really nice patio outside where you can see the Menomonee River. 
  • Eagle Park Brewing: This brewery has many different options, including milkshake IPAs, hazy IPAs, and hard seltzers. It’s a large brewery, so you can always find seating, even on the weekends or other busy periods. 

milwaukee skyline, sunset over the skyline, clouds streaking across the sky, giant boat in the harbor, places to visit near chicago, short trips from chicago

Getting to Milwaukee

If you have a car, it’s easy to get to Milwaukee in about an hour and a half using the I-94 W. You can also take a train, as Amtrak stations are in both cities. Hiawatha Service is the most common way to travel between the two cities.

3. Go Fruit Picking in Fenneville 

Around 2.5 hours from Chicago, Fenneville is one of the best day trips from Chicago. It’s in the fruit belt of Michigan, so it’s a great place for fruit picking. In the fall, you can pick fresh apples; in the summertime, you can get peaches and cherries. 

Pleasant Hill Farm and Crane Orchards are the most popular places for fruit picking. 

Before heading back to Chicago, stop by Crane’s Pie Pantry . It’s a beautiful winery and restaurant in a historic barn. They have amazing food and pies made with fresh fruit from nearby farms. 

Getting to Fenneville

The fastest way to get to Fenneville is to rent a car. The journey will take you about 2 hours and 20 minutes when you use I-94 E.

4. Visit Gurnee

Just one hour from Chicago, Gurnee is another of the best weekend road trips from Chicago. It’s home to Six Flags of America , so many rollercoaster fans come here for the weekend to get their adrenaline pumping. 

If you’re not an amusement park fan, there are many other things to do in Gurnee, including:

  • The Chocolate Sanctuary : This restaurant has a nice breakfast buffet, including freshly baked bagels. The chocolate-covered strawberries are a popular item on the menu. 
  • Illinois Beach State Park: Come here in the summer to lounge on the beach, pick wildflowers, and spot more than 600 different species of plants. 
  • Only Child Brewing Company : This brewing company has something for every palate, including IPAs, citrus fruit beers, and beers aged in wine barrels. 
  • Lambs Farm : A small farm that’s also an animal shelter, Lambs Farm is a nonprofit that employs people with disabilities. You can spend time with the animals, grab a treat at the bakery, and play mini golf. 

Getting to Gurnee

The only option to get to Gurnee from Chicago is to rent a car, as there are no good bus or train options. The drive only takes about 45 minutes on I-94 W, making it a super easy day trip.

5. Tip Toe Through the Tulips in Holland 

This small town in Michigan is 2.5 hours from Chicago. Spring is the best time to visit, so you can see the tulips in bloom. At the peak in spring, the town boasts over 4.5 million tulips. 

The best places to see the tulips are Windmill Island Gardens and Veldheer Tulip Gardens . 

There is also a tulip festival in early May that is worth checking out. You can try Dutch food, see traditional Dutch dancing, and even watch a few parades that go through the city center. 

There’s also the Holland Museum , which you should check out if you’re interested in Dutch culture and cuisine. 

Spring is the best time to see the tulips, but it’s not the only time of year when there are festivals. Come in late November if you’re interested in the Parade of Lights or Dutch Winterfest. 

bright yellow tulips in front of dutch architecture building

Getting to Holland

There are a couple of options for getting to Holland from Chicago. One is to rent a car, and the other is to take the Amtrak train . Many people choose to take the train as no transfers are, making it an easy journey.

The train will take about 3 hours. It can be pricey, though, with tickets costing up to $90 one way. If you travel with many friends, it might be cheaper to split the cost of a rental car and fuel.

6. See the Flowers Blooming in Chicago Botanic Gardens

For one of the best short trips from Chicago, you can drive about 35 minutes to get to the Chicago Botanic Gardens. The landscaping is beautiful, and flowers bloom through spring, summer, and early fall. 

The botanical gardens are divided into thirty separate smaller gardens, all with distinct flora and fauna. 

Once you get to the gardens, you can download an app on your smartphone that guides you down the different pathways in the park. A voice narration provides information about the different flowers and garden designs. 

On-site, there is a small restaurant and cafe . There is also a bike rental shop, as some parts of the gardens allow cycling. 

Chicago Botanic Gardens is located at 1000 Lake Cook Rd, Glencoe, IL 60022, United States . They’re open from 10 a.m. to 6 p.m. Tickets start at $11.95. 

Getting to Chicago Botanic Gardens

You’ll definitely need to rent a car to get to Chicago Botanic Gardens from Chicago. The easiest way to get there is to use I-94 W and then get off onto US 41. It will take you just under 30 minutes to get there.

7. Go Horse Riding in Indiana Dunes National Lakeshore 

If you’re interested in a one-day beach trip from Chicago, head to the Indiana Dunes National Lakeshore, just an hour outside of Chicago. The shore is about 15 miles long and is perfect for relaxing when the weather is warm. 

There are also many trails around the shore to go hiking, biking, or horse riding. If you’re interested in birding or want to explore more of the lakeshore, stop at the visitor’s center and ask to go on a walking tour led by one of the park rangers. 

Indiana Dunes National Lakeshore is located at 1215 N State Rd 49, Porter, IN 46304, United States. It’s open from 7 a.m. to 11 p.m. Entrance tickets are $15 if you don’t have a car and $25 if you do have a car. 

indiana sand dunes national park shoreline, grassy field with trees in the background

Getting to Indiana Dunes National Lakeshore

There is a bus option to get to the lakeshore, but I don’t recommend it as it makes the day very long, and the buses don’t come super often. Renting a car is your best option, and it takes about 45 minutes to get here from downtown Chicago.

8. Tour the Anderson Japanese Gardens 

For another of the best Chicago road trips, head about an hour and 40 minutes outside of the city to Anderson Japanese Gardens. You can walk down the quiet, peaceful trails and see the gardens John Anderson and Hoichi Kurisu designed. 

You can also take a guided tour. The guides can tell you more about the plants and the garden’s design. 

Open in 1978, the gardens were designed using different plants, water, and stones to provide a more authentic Japanese garden feeling. 

The Anderson Japanese Gardens are located at 318 Spring Creek Rd, Rockford, IL 61107, United States . Hours vary by season , and they are closed during the winter months. Tickets are $11.  

Getting to Anderson Japenese Gardens

To get to the gardens from Chicago, your best choice is to rent a car. If you drive along I-90 W, you can reach the gardens in about an hour and a half.

9. See the Discovery Center in Rockford, Illinois

Anderson Japanese Gardens is located in Rockford. So, after visiting the gardens, you can stay a little longer and explore this charming small town. 

This is a great place to visit if you bring the kids, as there are many family-friendly activities like the Discovery Center Museum .

You need to make reservations online before coming. There are over 250 exhibits to visit, so you can easily spend a whole day here. 

If you’re not with the kids, head to Prairie Street Brewing . Along with great local beers on tap, they also have bar food with a twist. Try the spicy mac ‘n’ cheese or the Asian street tacos. 

Getting to Rockford, Illinois

If you don’t want to rent a car, you can take a bus from Chicago to the Amtrak Station in Rockford. From there, you must take an Uber to the Discovery Center Museum.

If you choose to rent a car, you can drive directly to the Discovery Center on I-90 W.

10. Go to a Festival in Cedarburg, Wisconsin 

This cute town in Wisconsin is about 20 miles from Milwaukee and 2 hours from Chicago. Many family-owned places exist, including the wine bar Cedar Creek Winery and a famous candy apple store called Amy’s Candy Kitchen .

The city is also well known for having festivals in the fall that attract many different visitors, including Oktoberfest and the annual Wine & Harvest festival .

Getting to Cedarburg

Definitely rent a car to get to Cedarbug, as bus and train options are super limited. it takes about 2 hours to get to Cedarburg from Chicago.

11. See Bison at Midewin National Tallgrass Prairie

You might already know that Illinois is nicknamed the “prairie state.” This is because there are tons of uninhabited land where animals, like bison, roam freely.

To get a close-up look at these incredible animals, head to the Midewin National Tallgrass Prairie.

The place is pretty large, so you might have to spend several hours looking for the bison. Most travelers can spot them from the Iron Bridge Trailhead. You should also consider bringing a photo lens that can zoom in or a pair of binoculars so you can see the animals better.

There are also a few hiking trails throughout the prairies where you can see other wildlife and their natural habitats.

Getting to Midewin National Tallgrass Prairie

The only way to get to the prairies is to rent a car, as they are in a pretty rural area. You can drive along I-55 S to get here, and the journey will take about an hour.

three bison roaming in the prairies, one laying down and the other two eating

Top Things to Do in Chicago

Planning on spending time in Chicago in between a few fabulous day trips? Here are the top things to add to your Chicago bucket list:

  • The Art Institute of Chicago : All art lovers should head here on their first day in Chicago. The permanent exhibits showcase pieces of art from all over the world. Make sure to check the calendar to see which rotating exhibits they have while you’re visiting. 
  • Cloud Gate : This is the famous mirror bean that you have probably seen many photos of while planning your trip to Chicago. It’s an iconic piece of Chicago history that is worth seeing. 
  • Millennium Park : The perfect place in the city for people-watching, grabbing a snack, and relaxing. In the winter, there is an ice rink where you can go skating. 
  • Eat deep-dish pizza: Eating pizza is a must while in Chicago. The best places to enjoy pizza in the city are Giordano’s and Lou Malnatis . 
  • Gaze at the architecture: One of the first things you’ll notice when walking around Chicago is the beautiful buildings. Try to join a walking tour so you can be sure not to miss any of the best architectural spots. 
  • Hit the clubs: Chicago is known for having an amazing nightlife scene. If clubbing isn’t your vibe, there are many laid-back bars around the city as well. Raised Urban Rooftop Bar is one of the best places to drink, with nice views of the skyline. 

chicago bean, cloud gate, reflection of the buildings in the metal bean

How to Get to Chicago 

Chicago has a huge international airport, making the city very accessible for domestic and international travelers. Chicago O’Hare Airport (ORD) has daily flights from locations all over the world. 

You can find flights on American Airlines , Delta , and cheaper carriers like Spirit and Frontier. International airlines like KLM , Ethiopian Airlines , and Turkish Airlines also fly to Chicago. 

When to Visit Chicago 

Chicago has brutally cold winters, so it’s best to avoid coming to the city during that time. The months with the mildest weather include April through October. If you really hate chilly weather, the latest you should come is in September. 

The summer and early autumn months also have many different festivals making it a great time to be in the city. 

Don’t Miss These Incredible Day Trips from Chicago! 

From small local towns to state parks to famous botanical gardens, there are some amazing day trips from Chicago. While many more didn’t make this list, these are the ten best day trips to check out when you’re in the Chicago area. 

Are you heading to Chicago? Which of these day trips are you going to take first?

You Might Also Like

  • The 12 Best Places to Stay in Chicago: Areas & Accommodations
  • What to Do in Chicago for a Weekend

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This post was contributed by Natalie Castle. Natalie has been traveling mostly solo for the past 6 years internationally and across the United States. She loves seeing new destinations, especially where she can go to the beach or go for a long hike. She discovered her love for travel writing a few years ago and hopes to encourage other people to begin solo traveling through her writing. When she’s not working, you can find her with a glass of red wine planning her next trip.

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The 10 Best Day Trips From Chicago

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The city of Chicago has much to offer locals and tourists; however, getting out of town and seeing what’s nearby is worthwhile. From brewery tours in Milwaukee to Dutch heritage in Holland, Michigan, to hiking in state parks or along rivers and lakes, you’ll find that the surrounding areas of the Windy City offer a plethora of experiences. Pick and choose from these nearby adventures and plan your great escape. 

Holland, Michigan

 Holland Area Visitors Bureau

While Holland is a year-round destination, with lots of Dutch shops, architecture, windmills, restaurants, and museums to explore, spring is really when this city shines. See 4.5 million tulips in bloom around the town at Veldheer Tulip Gardens and Windmill Island Gardens. The Tulip Time Festival kicks off in May with Dutch food, music, parades, and Klompen dancing.

No matter when you visit, however, be sure to stop by the DeKlomp Wooden Shoe and Delft Factory and the Holland Museum. Also, the Dutch Winterfest and Parade of Lights are worth a look-see in November.

Getting There: Located midway between Chicago and Detroit, Holland is a three-hour drive away. Take I-94 east, exit 34 to I-196, and then exit 44 to Holland.

Travel Tip: Michigan’s most photographed lighthouse is Big Red Lighthouse in Holland. Visit Holland State Park for the best view of the tower—walk the boardwalk to the north pier (wheelchair accessible). 

Indiana Dunes National Park

 Wendy Altschuler

Our country’s 61st National Park, Indiana Dunes National Park , has much to offer in a tight package. Swim and hike in the summer or snowshoe and cross-country ski in the winter. Play on 15 miles of Lake Michigan’s southern shore, watch for migrating and regular nesting birds—hawks, wetland birds, woodpeckers—and hike on 50 miles of trails that cut through and over dunes, wetlands, prairies, forests, and rivers. Keep your eyes out for threatened Pitcher’s thistle and snap photos of white-tailed deer, the largest herbivore found here. The Great Blue Heron rookery can be found along the national lakeshore as well.

Camp overnight at Dunewood Campground or fish in the Little Calumet River during the warmer months. Get the Geocaching app on your phone and find hidden containers while also enjoying nature and being outside. History buffs will enjoy visiting one of the sixty historic structures—the Bailly Homestead, Camp Good Fellow, Chellberg Farm, and a handful of houses from the 1933 World’s Fair are the most significant.

Getting There: To get to the park, take Interstate 94, exit 26 north; the Indiana Toll Road (I-80/90), exit 31 north; U.S. Highways 12 and 20, or other state roads. The Indiana Dunes Visitors Center is on Indiana State Road 49.

Travel Tip: Kids can become Junior Rangers and visit the park with a Discovery Guide. Also, park rangers can lead tours throughout the park. Stop by the Visitor’s Center to map out your adventure. 

Kettle Moraine State Forest


Home to 30,000 tree-filled acres with rolling hills, grasslands, lakes, and forests, Kettle Moraine State Forest is the ideal place to enjoy the outdoors. Ride horses and bicycles, hike, cross-country ski, snowshoe, and drive the Kettle Moraine Scenic Drive to explore the kettles (depressions) left by the Ice Age. Only two hours and 40 minutes from Chicago, this destination is ideal for a day trip.

Getting There: To get to this Wisconsin State Park, located between Madison and Milwaukee, take I-90/94 west toward Milwaukee, exit 344 to US-12 west.

Travel Tip: Wade House Stagecoach Inn, Holy Hill Basilica, Cushing Memorial Park, and numerous geological landmarks and small towns can be seen along the drive. 

Lake Geneva

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If you want to see Gilded Age mansions built by well-heeled Chicagoans, visit the lakeside Shore Path in Lake Geneva. The area also offers shopping, diverse dining, local beaches—including Big Foot Beach State Park—and outdoor fun. Stay overnight at a campground or Bed and Breakfast, ride the U.S. Mailboat and watch jumpers deliver mail while the boat keeps moving, go kayaking, visit a winery or brewery, or hit a round of golf—there’s something to do for every age and ability at Lake Geneva.

Getting There: Take 294 north toward Wisconsin, continue to I-94 west, and exit at 344 onto WI-50 toward Lake Geneva.

Travel Tip: Request a free Visitors Guide at Visit Lake Geneva.

Chicago Botanic Gardens

 Getty/N. Vivienne Shen Photography

Just one hour north of Chicago sits Chicago Botanic Garden , a haven for plants and flowers from around the globe. Plan on spending a few hours here, exploring the grounds, having lunch or a snack at the Garden View Café, and shopping for unique items in the Garden Shop. A cart positioned just over the bridge from the Visitor Center lets you know what is currently in bloom so that you can make the most of your visit.

Admission is per person; buy tickets in advance to get the best pricing and to ensure your preferred date and time; a parking fee is purchased separately. Admission includes summer attractions such as Butterflies & Blooms, Grand Tram Tour and Model Railroad Garden.

Home to nearly 30 different display gardens spread over almost 400 acres; these gardens give visitors a chance to learn about various plant collections. This living museum is well-known for its Bonsai Collection, Japanese Garden, English Walled Garden, Dwarf Conifer Garden, and multiple greenhouses that nurture rare, edible, seasonal, and flowering plants from around the world.

Getting There: From Chicago, take the Kennedy Expressway (I-90/94) west to Edens Expressway (I-94) and U.S. Route 41. Take the Lake Cook Road exit and drive a half-mile east to the destination.

You can also take the Metra train on the Union Pacific North Line and get off at the Braeside station. From there, walk just under a mile to the gardens on the North Branch Trail, which is quite lovely.

Travel Tip: Kids love the Model Railroad Garden, open half of the year, which features 18 trains chugging along over bridges, through tunnels, and past nearly 50 different American landmarks. 

Starved Rock State Park

Getty/Rudy Balasko

Starved Rock State Park is a family-friendly—and dog-pro—park that features lofty sandstone bluffs that loom large, especially in contrast to the flatlands that the state is known for. See 15 canyons, towering trees, flora and fauna, and waterfalls while you hike along the Illinois River. The most scenic waterfalls—especially after snowmelt or rain—can be found in French, Wildcat, and Kaskaskia canyons.

Getting There: Starved Rock is about 90 miles west of Chicago, south of I-80, near the town of LaSalle.

Travel Tip: Crowds over holidays and weekends in the summer months can be obtrusive—visit during the week if possible or in the off-season.

Six Flags Great America

 Six Flags Great America

Six Flags Great America has a brand new ride to lure in visitors: Maxx Force, a record-breaking roller coaster. Reaching speeds of 78 miles per hour in just under two seconds, this ride features the fastest and tallest inversion of any roller coaster in the world. Also, the park has over 30 different rides and attractions, a 20-acre water park, various shows and themed entertainment, character meet-ups, and four different children’s areas for the younger crowd.

Getting There: From the city, take I-94 or I-294 west, drive for just under an hour, and exit at Grand Avenue (Route 132) in the village of Gurnee. Six Flags will be just off the ramp on the right.

Travel Tip: The entrance to the park is often busy during peak summer months (parking in the overflow parking is a good sign that there’s a long line at the door). Arrive early, before the gates open, to avoid long waiting times. Also, park hours are subject to change and do so seasonally, so be sure to check the website for operating hours. 

Milwaukee, Wisconsin

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From macro to micro, Milwaukee, also known by the moniker Brew City, has pints for everyone’s taste buds. Pabst, Schlitz, Blatz, Miller—all well-known Milwaukee favorites. This beer-happy city’s roots trace back to German immigrants from the 19th century—they brought their brewing know-how with them.

The Bavarian Bierhaus , a German beer hall with a restaurant, beer garden, and brewery, is a resident favorite. City Lights Brewing Company is another great option, especially for history buffs—the brewery is located in the 115-year-old Gas Light Building. Historic architecture and modern-day brewing techniques are the highlights of the tour, available on Fridays and Saturdays. Milwaukee Brewing Co. offers weekend “Beer in Hand” tours through its craft brewery, where you can sample seasonal delights and use the token for a free beer at bars nearby.

Getting There: Located on the shores of Lake Michigan, 90 minutes from Chicago, Milwaukee is accessible by train or car. From Chicago, by car, take I-294 north to 94 west. Exit at I-794 east (exit 310 C). Or, take the Amtrak from Chicago to Milwaukee, getting off downtown at Milwaukee Intermodal Station.

Travel Tip: Of course, there are lots of breweries to choose from, and you may want to join an organized walking or shuttle tour. Visit Milwaukee is an excellent resource for planning out a beer tour. 

Abraham Presidential Library and Museum

Randy von Liski / CC BY-NC-ND 2.0 / Flickr

Learning activities, hands-on exhibits, civil war artifacts, and more bring people from all over the world to this museum and library. You’ll have the chance to immerse yourself in the history and stories of America’s 16th president of the United States.

Getting There: Take I-290 east to I-355 south to I-55 south, exit at 98 B onto IL-97 west.

Travel Tip: Many events and special happenings occur throughout the year. Be sure to check the museum’s website to see if the scheduled activities align with your plans. 

Morton Arboretum

Special days throughout the year allow dogs inside the Morton Arboretum . For only $5 per dog, leashed animals can hike the trails, receive a bandana, and meet other canines as you explore the arboretum. The Tails on the Trails event is full of vendors, activities, and contests (how fast do you think your dog can lick peanut butter off of a spoon?).

Getting There: The Morton Arboretum, just west of I-355 and north of I-88 on Illinois Route 53, is located 25 miles west of Chicago.  

Travel Tip: Make sure your dog is up-to-date on vaccinations and is friendly around humans and other dogs. 

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5 Best Day Trips from Chicago

By Joseph Hernandez and Jessi Roti

Holland Harbor Lighthouse

Are you visiting Chicago but your wanderlust feels like an itch you can’t scratch? No worries. The city is the gateway to the rest of the Midwest, and there are plenty of trips within a short drive or train trip that require only a day or two to explore and enjoy. Check out a painterly tulip farm in Michigan or devour the craft beer and cheese curds in Wisconsin. Whether you pick Milwaukee or Lake Geneva, Wisconsin; Oak Park or Mount Vernon, Illinois; or Holland, Michigan, these excursions prove the Midwest is anything but fly-over country.

Click the link to read our complete Chicago city guide .

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

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Want out of Chicago but still need to feel the pulse of a buzzing metropolis? Milwaukee is your next stop. While known for its beer and brats, the city’s pride in its past is equally undeniable upon arrival. With the dedicated revitalization of neighborhoods such as the historic Third Ward, Lincoln Village, and others, visitors are kept busy by specialty shops, galleries, and restaurants, as well as more growing, creative businesses. With access to Lake Michigan and a number of other rivers with paved pathways, there are plenty of nooks downtown for taking a break to take in the view. Milwaukee has a little bit of it all.

Milwaukee Public Market St Paul Fish Company

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This bustling public market is stuffed with local shops and restaurants in the heart of Milwaukee's historic Third Ward neighborhood. Each of the vendors are independently operated, and each offer different food and shopping experiences. The market invites you to divide and conquer, so bring your most inquisitive or adventurous friend to sample each of the vendors. Create a DIY tapas-style crawl, or shop vendors for tasty souvenirs.

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Located in the heart of Milwaukee, Lakeshore State Park is an urban escape. Twenty-two acres of lakefront trails and paths look out onto Lake Michigan, with fishing areas, a watercraft landing for canoes and kayaks, and connecting access to Summerfest, Milwaukee's annual large-scale music festival. Trails are clearly marked with little chance of getting lost, where leisurely walkers and cyclists are soaking in the views.

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The lakefront Milwaukee Art Museum is a vision in and of itself. The gleaming white Santiago Calatrava structure, with dramatic wings and stunning dorsal fin, hints at the talent within the quiet galleries inside. With a collection of over 25,000 works, the Milwaukee Art Museum is one of the largest museums in the country. The galleries feature everything from folk art to contemporary American, across all disciplines like prints, sculptures, and paintings. Wisconsin native Georgia O'Keefe features prominently—the museum owns much of her work—alongside European artists Gustave Caillebotte, Claude Monet, and Joan Miró.

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Let Schuster Mansion comfort you in history and elegance, at the level of your choosing. Upon arrival, you'll be struck by it's rusty, red coloring—a blend of red sandstone, red brick, and red terra cotta trim. The mansion's stand-out coloring only hints at the interior design. Rooms are spacious, and each comes with a vintage, claw foot tub that taunts you with the promise of a luxurious bubble bath. Enjoy the lush, relaxing Victorian Garden or help complete the ever-ongoing jigsaw puzzle in the Ladies’ Parlor. Planning on visiting ahead of the winter holidays? Schuster's Christmas decor is second to none.


Holler House Arrow

Founded as Skowronski's in 1908 in the Lincoln Village neighborhood, the noisy tavern was renamed Holler House after a local woman complained about the ruckus emanating from inside. But the bar has seen many boozy hijinks in its century-plus existence. Known for its raucous bowling nights—in a slight basement alley featuring two lanes that happen to be the oldest, sanctioned tenpin lanes in the United States, still set by hand—Holler House is where you can go to really let loose. In addition to playing a game or two, there’s a full bar, but this is much more of a beer and a shot establishment .

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Sharing a border with Chicago’s West side, suburban Oak Park is accessible via the CTA’s Blue and Green Lines as well as Metra trains. But its proximity to the urban hustle doesn’t disrupt its refreshing slow pace. Enjoy its homegrown Arts District, unique boutiques, cafés, and rich cultural record—including being the home of actress Betty White and novelist Ernest Hemingway. Known for its abundance of Prairie School architecture, thanks to natives such as Frank Lloyd Wright, the neighborhood also makes for great self-guided tours on bike or on foot. Whether you’re a fan of local history or everyday whimsy, a visit to Oak Park is worth it.

Frank Lloyd Wright House and Studio Tour Dining Room Facade

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Designed, worked, and lived in by one of the biggest names in American architecture, the Frank Lloyd Wright Home and Studio preserves the Prairie School founder's original architectural studio and his adjacent home where he experimented with early ideas. Wright designed the buildings and filled them with his own furniture designs, too, a marriage that offers a comprehensive look at Wright's insistence on design integrity.

Pleasant Home Museum Interior Library

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Set in Oak Park's sprawling Mills Park and designed in 1897 by architect George W. Maher, this home is a National Historic Landmark and the only Maher building open to the public as a museum. While Frank Lloyd Wright is the bigger name, his peer Maher helped usher in the Prairie School of architecture with Pleasant Home's design, helping to influence the blending of oeuvres that defined the style. This 30-room museum showcases late 19-century craftsmanship, from intricate art glass to custom woodwork throughout.

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A once-popular summer vacation destination for wealthy urbanites, Lake Geneva has managed to preserve much of its Gilded Age lure. Think a little Great Gatsby in the Midwest. Though tastes have changed, Lake Geneva has managed to stay at the top of many travel recommendation lists—mainly for its year-round resort-like atmosphere and attractions. A place that’s almost always prepared for tourists has its perks and one of this Wisconsin town’s is its genial nature, whether you’re perusing different markets or rubbing elbows at the bar. Visitors can also explore local arts culture. Scenic, lakeside paths and parks are calling your name. Or if you’re feeling adventurous, fly above it all in a hot air balloon.

Lake Geneva Wisconsin

Lake Geneva Shore Path Arrow

With 26 miles hugging the shores of well-trodden Lake Geneva, the Shore Path is not exactly removed from the Realm of Man, but it is a scenic stroll nonetheless. Wealthy Chicagoans flocked to Lake Geneva in the 19th century, especially after the Great Fire in 1971. You'll find stunning former estates and opulent lawns. By public ordinance still in effect today, property owners leave at least 20 feet of space available to the public, with some offering benches to rest or art installations to view and interact with as you make your way around the path.

Baker House Historic Hotel Lake Geneva

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Baker House, constructed in 1885, houses an opulent Gilded Age parlor, with sunny lakeside views, and homey digs. Guests flock there for its old-school charm and luxurious furnishings, trying to tap the wealthy turn-of-the-century vibe that attracted well-heeled vacationers to Lake Geneva in the first place. For turn-of-the-century charm and opulence, Baker House delivers on all fronts.

Studio Winery Lake Geneva Wisconsin Exterior

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Exposed steel beams, warm wood wine racks, and art made by Studio Winery's artist owners create a warm, convivial atmosphere for wine drinking. The large room features many high-top tables for groups to sit and enjoy, plus a small stage for visiting music acts. The wines aren't technically fine wines, but they're fine wines—get it? The Musician series wines take their name from famous musicians, using local varietals and range from dry to sweet. Meanwhile, the premier tasting wines feature more elegant, classic European varietals, like viognier, syrah, and cabernet sauvignon.


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Housed within Lake Geneva's Fancy Fair Mall, this indoor artisan market is open year-round, showcasing original wares by more than 100 makers from across the country. Queen Bee’s curated collections cater to all ages, so even kids will be able to make a day out of shopping and supporting small business. Whether you’re looking for hand-forged, industrial lamps, a housewarming gift for a friend who you know loves a sassy statement mug, candles, decorative signage, or unique clothing, the market is a great place to find one-of-a-kind, useful souvenirs from your visit.

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Holland’s Dutch immigrants are celebrated in the aesthetics and traditions of this shore town’s varied restaurants, shops, attractions, and architecture. You’ll notice antiqued windmills, re-envisioned Germanic villages, dainty gardens, and millions of tulips, which give it the nickname Tulip City. Stroll or hike through the park before taking in the sunset over Lake Michigan, then go out for drinks. While there’s plenty of activity to occupy you during the day, the star-gazing Holland’s country outskirts allow for is unparalleled. What better way to end a day? Play Sufjan Stevens’ Greetings from Michigan album on your way up, track 7—“Holland.”

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Located on a quiet country road, Castle in the Country is a quaint, 100-year-old Victorian that screams iconic American dream home. The bed and breakfast, with its millennial pink painted details, wrap-around porch and just-so hanging planters, is an adorable escape out in flat, picturesque countryside. Castle in the Country's seclusion is its biggest draw. Far away from city lights, you'll be beneath star-filled skies and amidst wide-open spaces. The luxurious digs and clean country air are enough reason to book a stay.

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Windmill Island Gardens Arrow

Want a taste of old-school Europe? Holland's Windmill Island Gardens, a 36-acre park of even-keeled fallow land, manicured gardens, and quaint recreation Dutch shops is such an escape. The main attraction at Windmill Island Gardens is its namesake, DeZwaan ("The Swan"), a windmill built in 1771 but purchased and imported from the Netherlands in 1964. The working mill still grinds flour, available for purchase in the "Little Netherlands" shops, which also sell kitschy crafts like pottery and wooden shoes. With 100,000 tulips planted annually, the gardens also participate in Holland's famed Tulip Time festival, with activities for kids and adults alike.

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Veldheer Tulip Gardens Arrow

With over five million tulips planted annually, Veldheer Tulip Gardens is a sight to behold come spring-time. The manicured lawn explodes in color, much like you'd expect in the real Holland, with tulips of every hue brightening the landscape. Though you're not allowed to pull the tulips from the ground, plenty of bulbs are available to order, as are other flowering plants. You think it's just all pretty flowers here? Think again. Veldheer also started a breeding program for American bison, with a herd of 20 available for viewing, with educational programing for the public. Veldheer’s grounds also include the DeKlomp Wooden Shoe Factory—a perfect gift to snag before you go.

Butch's Drydock Holland Missouri Food

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This stylish bistro is a welcome respite, with white table cloths, warm lighting, and local art on walls. A small list of tightly curated wines spans the globe, but the draw here is Butch's 200-plus beer selection, spanning micro, craft, and imported beers and ciders. The menu is a selection of New American classics, and Butch's prides itself on working closely with local purveyors, listing its local partners prominently on the website. When in Holland, head here for a sophisticated, special dinner that is elevated but unfussy.

New Holland Brewery Interior Holland Missouri

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Founded in 1996, New Holland Brewing is one of the country's pioneering microbreweries. At its corporate headquarters in downtown Holland, you'll find the brewpub. The sprawling, two-floor pub is familiar in the way that breweries can be, that is, exposed ducts and bricks, tin ceilings and numerous myriad high-tops occupied by imbibers is familiar. From cask-poured stouts to limited releases, growler fills and special brewpub-only offerings, New Holland serves upwards of 20 brews at any given time. Head there for a low-key lunch or dinner. Meet new friends or catch up with old ones over cold brews in relaxed digs.

de Boer Bakkerij bakery holland missouri exterior

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This family-run spot has been baking in Holland, Michigan for four generations, adding the cozy breakfast and lunch restaurant in 2008. The bakery bustles with to-go diners in the mornings, with cafe bar seating, benches, and banquettes for restaurant diners. The high ceilings and bright lights make for an airy space. DeBoers started as an authentic Dutch bakery, so it's safe to assume that the baked offerings are on lock: Challah, cracked wheat, San Francisco sourdough, French baguette, marble rye—the list goes on.

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Along the shores of Lake Michigan, this 22-acre park is a popular place for swimming, sunbathing, and picnicking—but it’s called Tunnel Park for a reason. What locals consider the best spot to watch the sunset, a unique archway built through a dune gives way to pure, unobstructed views of orange and amber skies. You may even spot a sailboat or two.

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Small town Mount Vernon (named after President George Washington’s Virginia plantation) has all the modest charm expected from Southern Illinois, and passionate locals are at the heart of efforts to bring more tourism to their town. Home to Rend Lake, a groovy vinyl record shop, comforting spots to grab a bite, the Cedarhurst Center for the Arts, and plenty of wide open spaces, Mt. Vernon might not be what immediately comes to mind when one thinks about visiting the Prairie State—but its surprising creative spirit may just capture a spot on your return travel list.

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At the only locally-owned vinyl LP shop in town, wafting incense will greet you ahead of your dive into the expanse of classic rock albums, R&B, and jazz albums, rare imports, and more, among plenty of band t-shirts to show an even deeper allegiance to your favorite acts. A number of CDs and concert DVDs are also available in the store’s collection, but management is positive it can track down any disc you’re after.

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Though King City Books’ is under renovation, the shop’s reputation precedes it—diehard patrons sing its praises for the reads and espresso bar it houses. It's the only indie bookstore within 60 miles, making its devoted fan base even more important. The shop is dedicated to elevating local authors and selections fit for all ages, including mystery and YA. Locals are devoted fans of this book shop and are eagerly awaiting its return, as are musicians and artists who took advantage of the shop's open mic nights.

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Across the Cedarhurst Center's 90-acre campus, early 19th and 20th century paintings and modern sculpture are showcased. Most of the collection is from that of the museum's founders John and Eleanor Mitchell. Take a stroll or drive through the Goldman-Kuenz Sculpture Park for some perspective. Across the center’s 90-acre campus, works by John Kearney, Chakaia Booker, Deborah Masuoka, Tom Orr,and many more are thoughtfully placed for guests to develop a deeper appreciation for modern sculpture. Inside, the Bonan Permanent Collection is at the heart of the museum—an abundant celebration of paintings by early 19th and 20th century American masters, both renowned and unsung.

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Rend Lake offers a slew of water sports and other outdoor activities that are difficult to properly enjoy within Chicago city limits. Known as “Southern Illinois’ playground,” you could plan a day’s worth of events based solely on what the lands have to offer. Hit one of the lake’s two beaches (but prepare to pay a daily fee) or take advantage of the thousands of acres of open water for skiing, jet skiing, wake boarding, or tubing.

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Nestled between the trees, this quaint bed and breakfast offers a glimpse at simple, sophisticated small-town living. With boutique amenities, lovely gardens, and owner Mr. Sidwell's library of books and art collection, this stay encourages serenity at both the start and end of your day. Each morning, you’ll be greeted with a full, home-cooked breakfast and probably a look or two from Sidwell’s resident English Bulldog. She doesn’t have the run of the house, but she’s certainly one of the ladies of it. The bed and breakfast is blocks away from the Cedarhurst Center for the Arts, a few miles from Rend Lake, and other Mount Vernon sites including wineries.

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This unassuming gyro shop has been a Mt. Vernon staple ever since it began serving Greek comfort food in 1978. The menu hasn’t changed much over the years (it’s still cash only), and neither has the décor, but it’s part of why the place is so beloved. Get a gyro and fries with a piece of baklava on the side, kalamata olive salad, or—if there’s a bit of chill in the air—warm up with a bowl of gyro stew: the juicy, tangy bite you love served in a rich, brown broth with chunky veggies and potatoes. The stew is the entree to choose for something quintessentially Jimmie James.


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Locals frequent for breakfast, lunch, and dinner as well as shop the small grocery inside the cafe. But rowdy, this cafe is not. The café offers a number of housemade lemonades, smoothies, hot and iced teas, coffees and frappes, and soft drinks. With its down-home appeal, pies, pecan rolls, biscuits, donuts, and scones all have the feel of grandma’s hands. Stop in for breakfast or lunch—which includes everything from panini to lasagna and meatloaf—or homemade ice cream after a day at the lake.

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Fenn Valley Vineyards Arrow

This longtime, family-owned vintner features a warm, rustic tasting room, tours, and wine-pairing dinners in a convivial atmosphere. The winery hosts majority group tastings for special occasions and picnics. As the wine continues to flow, so does conversation. During select times of year, the vineyard offers specially designed tours involving food and wine. Picnics include a hearty charcuterie board, choice of three bottles of wine or 3-4 packs of hard cider, and a battery-powered speaker with cables to connect to your phone or tablet.


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Railroads & Locomotives Tourist Railroad Profiles Amtrak Hiawatha Chicago day trip

Amtrak Hiawatha Chicago day trip

| Last updated on April 6, 2023

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Riding a passenger train and back is as easy as taking a seat between Milwaukee and Chicago

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Amtrak Hiawatha Chicago day trip: Chicago is indisputably the heart of American railroading.

Passenger train about to pass over water on a bridge in a city landscape.

Represented by six Class I railroads, Amtrak, Metra, the South Shore Line, Chicago Transit Authority, and a long-list of short line and regional railroads, the city offers a magnitude of rail focal points and it’s little surprise that access to Chicago’s greatest sights can be enjoyed without the hassle of navigating a vehicle. For those in Milwaukee and northern Illinois, a day trip on Amtrak’s Hiawatha affords great access to downtown Chicago with a number of daily trains that will deliver you back to the Brew City before bedtime.

Weekday and Saturday trains currently depart south from Milwaukee as early as 6:15 a.m. Central Time onboard Hiawatha No. 330, while six additional daily trains provide timely service to the Windy City with staggered departures from Milwaukee. Southbound Hiawatha No. 332 departs at 8:05 a.m. CT; No. 334 at 11 a.m. CT; No. 336 at 1:05 p.m. CT; No. 338 at 3:00 p.m. CT; No. 340 at 5:45 p.m. CT; and lastly, No. 342 at 7:35 p.m. CT.The Hiawatha’s southbound trips begin at Milwaukee’s Intermodal Station located at 433 West St. Paul Avenue.

Overhead view of a train in a canyon of large buildings.

Originally built by the Milwaukee Road to serve its passenger train of the same name, the then- Milwaukee Union Station replaced the city’s Everett Street facility. Chicago & North Western Railroad passenger trains also used Milwaukee Union Station until the C&NW withdrew its passenger service from the region after the formation of Amtrak. The Milwaukee train station underwent a near-$17 million renovation and re-branding in 2007 and was renamed Milwaukee Intermodal Station. Upgrades included a larger waiting area, glass atrium, additional ticketing facilities for rail and Greyhound bus service, and restaurant and retail space. Today’s station is served by Canadian Pacific’s U.S. subsidiary, the Soo Line, on its C&M Subdivision, appropriately named because of its link between Chicago and Milwaukee.

Southbound Hiawathas follow the original Milwaukee Road mainline south for a distance close to 40 miles before crossing into Illinois near the town of Russell. The first half hour of the passenger train ride is spent through suburban Milwaukee, passing CP’s Muskego Yard (MP 83.4) and serving the city’s Milwaukee Airport Rail Station and Sturtevant, Wis., before entering Illinois. For rail enthusiasts, the first significant attraction is 53 miles south of Milwaukee at Roundout Tower (MP 55.0) where the CP’s ex-Milwaukee Road main crosses the CN’s former Elgin, Joliet & Eastern. South of Roundout, Hiawatha trains operate on tracks under Metra’s jurisdiction as part of its Milwaukee North Line service. CP freight dispatchers still dispatch the territory and roughly 20 CP freight trains utilize the old Milwaukee Road each day, as well as Amtrak’s daily Empire Builder.

South of Roundout, Hiawatha trains pass through suburban Wadsworth (MP 42.9), Lake Forest (MP 27.8), and Northbrook (MP 21.1) on the approach into Chicago. Here, Hiawatha trains will likely pass Metra commuter trains and perhaps a freight train as the Hiawatha approaches Chicago Union Station. Crossing the Union Pacific’s ex-C&NW at Mayfair (MP 8.9) and again at Grayland (MP 8.0), Hiawatha trains ease into Chicago Union Station a few miles later. From start-to-finish, Hiawatha trains reach Chicago Union Station in 1 hour and 42 minutes.

A three-quarter wedge image of a passenger train in a landscape suburban area.

Located at 225 South Canal Street, Chicago Union Station is one of Amtrak’s most significant touchpoints, serving as the nation’s third busiest train station and Amtrak’s fourth busiest. It serves more than 3 million Amtrak customers and 35 million Metra passengers each year with more than 300 trains per day. Today, nine Amtrak long-distance trains serve Chicago as well as three state-supported trains. Long-distance trains include the California Zephyr to Emeryville, Calif., Capitol Limited to Washington, D.C., Cardinal to New York, City of New Orleans to New Orleans, Empire Builder to Portland and Seattle, Lake Shore Limited to New York and Boston, Missouri River Runner to Kansas City, Southwest Chief to Los Angeles, and the Texas Eagle to San Antonio. Amtrak regional or state-supported trains include the Hiawatha to Milwaukee, Illinois Service to Quincy, Ill., St. Louis, and Cardondale, Ill., and Michigan Service to Grand Rapids and East Lansing, Mich., Port Huron and Detroit, Mich., and Pontiac, Mich.

From Union Station proper, Metra’s Milwaukee District North, North Central, Heritage Corridor, BNSF, SouthWest Service, Milwaukee District West services provide connections to most Chicago neighborhoods, enabling the rail-exclusive travel experience to continue to your desired neighborhood destination within Chicago.

It’s fair to say that Chicago offers something enjoyable for everyone, even beyond its vast rail history. Milwaukee travelers wanting to see a Chicago Cubs baseball game can gain access to   Wrigley Field by taking the Chicago Transit Authority Red Line onboard the city’s State Street Subway. Subway access is just six blocks east of Chicago Union Station. If onboard Chicago’s subway system, be sure to enjoy a ride on the subway’s Loop, a 1.7-mile circuit of elevated subway circling the city’s downtown core. Five of the CTA’s eight subway lines use Loop tracks today. It is estimated that more than 1.6 million passengers use the CTA each weekday, making it the second largest public transit system in the country.

If you’re looking for a less-crowded history lesson, Metra’s hub-and-spoke service coverage area affords direct rail access to quiet suburban neighborhoods where rail enthusiasts can enjoy a relaxing morning or afternoon enjoying a cup of coffee and watching a mix of freight and passenger trains. The author’s personal favorite is a ride out to Downers Grove on Metra’s BNSF line. Late evenings are particularly crowded with rush-hour commuter trains departing from Chicago, however if you arrive early enough in the afternoon one can enjoy both freight and passenger trains. BNSF Railway Z-train intermodals and a mixed bag of other carload and unit train traffic can be safely enjoyed from downtown Downers Grove, Naperville, or Aurora. Plan your visit to the suburbs accordingly as not to miss your northbound Hiawatha to Milwaukee.

Whether it’s a Chicago architectural tour a walk along Lake Michigan, a visit to Wrigley Field, or an afternoon railfanning , Chicago simply offers too much to enjoy in a single-day. As you plan your afternoon return trip to Milwaukee, know that most days will provide you seven northbound departures, assuming you arrived at Chicago on the earliest southbound train No. 330 (arriving at Union Station at 7:57 a.m. CT). Northbound Hiawatha No. 331 departs Chicago Union Station at 8:25 a.m. CT; No. 333 at 11:05 a.m. ET, No. 335 at 1:05 p.m. CT; No. 337 at 3:15 p.m. CT; No. 339 at 5:08 p.m. CT; No. 341 at 8:05 p.m. CT; and on Fridays only, No. 343 at 11:25 p.m. CT.

Tips & Recommendations:

  • If you venture out into the suburbs, carefully review Metra timetables, and give yourself enough time to return to Chicago Union Station before your Hiawatha departs.
  • Purchase a Chicago Ventra Card, an electronic fare payment card used for Chicago Transit Authority, Metra, and Pace transit systems. Ventra is an easy-to-use card compatible with smartphones and serving as single-source fare payment for all-things Chicago transportation.
  • Explore Chicago’s non-tourist-oriented restaurants in one of its urban neighborhoods such as the West Loop, River North, or Andersonville. There are too many local fares to list.

If you’re in a hurry in Milwaukee and need your breakfast, Aladdin’s All Aboard Cafe serves mostly a commuter crowd with simple prepared foods, hot sandwiches, and coffee in the station. If you have a little more time, or depart on a weekend, try the Stone Creek Coffee just a half a block north. Enjoy their fireplace, especially on a cold winter day.

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The Forge in Lemont

10 Chicago day trips for an easy getaway

Last updated on March 13, 2023 by Allana Mortell

Summer travel might look a little different this year, but that doesn’t mean you can’t still soak up the season with a short, sun-filled getaway. Luckily for Chicagoans, there are plenty of options, whether it’s admiring historic architecture in Oak Park, wandering renowned Japanese gardens, tackling an outdoor ropes courses, and so much more. Here’s a roundup of our top picks for a Chicago-area day trip.

Frank Lloyd Wright Home and Studio

chicago day trips by train

11 miles from Chicago It’s a quick drive or train ride from the city to suburban Oak Park, home to more Frank Lloyd Wright buildings than anywhere else in the world. Step inside the Frank Lloyd Wright Home and Studio to see where the famous architect lived and worked while designing his famous Prairie Style, the first uniquely American architecture. The studio offers guided, socially distanced tours both inside and outside the home. After the tour, be sure to explore the historic neighborhood to spot more of Wright’s Oak Park designs , like the nearby Unity Temple.

Pullman National Monument

chicago day trips by train

15 miles from Chicago One of the best ways to explore the historic South Side neighborhood of Pullman is by spending time at the Pullman National Monument . The historic district is Chicago’s one and only national monument, designated by President Barack Obama in 2015. A planned industrial utopia designed by luxury railcar tycoon George Pullman, the historic district also includes the National A. Phillip Randolph Pullman Porter Museum (temporarily closed due to COVID-19) and Hotel Florence . With plenty of open, grassy space, it’s the perfect place to wander and admire the unique architecture and history of the area.

Waterfall Glen Forest Preserve

23 miles from Chicago Hikers, bicyclists, horseback riders, and fishermen alike can all enjoy themselves at the Waterfall Glen Forest Preserve in Darien, Illinois. Only a short drive from the city, the 2,000-acre preserve includes a beautiful waterfall, a scenic bluff overlook, and over 11 miles of trails perfect for a summer hike away from the hustle of the city. Currently, the revised forest preserve hours are open an hour before sunrise until sunset.

Chicago Botanic Garden

chicago day trips by train

25 miles from Chicago The Northern suburb of Glencoe is home to the Chicago Botanic Garden , a lush display of 27 floral and plant-filled gardens sprinkled across 385 open acres. There’s plenty to explore at the Botanic Garden and the garden tours and trams are available to soak in the most popular and blooming areas.

Morton Arboretum

Morton Arboretum

26 miles from Chicago Located in suburban Lisle, the beloved Morton Arboretum is a public garden that includes over 1,700 acres and 222,000 live plants and trees. Perfect for nature lovers, the Arboretum houses both indoor and outdoor activities, including a 16-mile walking trail, children’s garden, museum and more. You’ll need to reserve a timed ticket in advance.

The Forge Outdoor Adventure Park in Lemont

chicago day trips by train

29 miles from Chicago For those looking for a Chicago-area day trip filled with adventure, The Forge: Lemont Quarries is a one-of-a-kind destination perfect for families and friends alike. This new adventure park, built on 300 acres of land in Lemont, Illinois, includes multiple rope courses, ziplining, climbing walls, hiking, fishing, mountain biking, yoga, and more. Advance reservations are currently required.

Indiana Dunes National Park

chicago day trips by train

44 miles from Chicago For many Chicagoans, summertime isn’t complete without a trip to the Indiana Dunes National Park . One of the country’s newest national parks, the Indiana Dunes is less than fifty miles from the city and features over three miles of lakeshore lined with dunes, marshes, grassland, and forests. Tackle the “ Three Dune Challenge ” (the equivalent of climbing 55 stories) during a day of hiking or relax with some sunbathing on one of the nine beaches .

Illinois Beach State Park

48 miles from Chicago More than 4,000 acres of Lake Michigan’s sandy shores await you at the Illinois Beach State Park in Zion, Illinois. This park, the only remaining beach ridge shoreline left in the state,  is filled with sand dunes, marshes, and forests meant for exploring during a leisurely beach getaway. The park is open daily for guests during the week, but summer weekends are now only open to registered guests of the Illinois Beach campground and Illinois Beach Hotel to help limit crowds.

Des Plaines State Fish and Wildlife Area

57 miles from Chicago For a day of tranquility, head to Wilmington, Illinois — an hour south of the city — and soak up all that Des Plaines State Fish and Wildlife Area has to offer. With water sports such as boating, jet skiing, and water skiing to land activities like an archery range and equestrian trails, there’s plenty of nature-filled fun the whole family can enjoy.

Anderson Japanese Gardens

Anderson Japanese Gardens

91 miles from Chicago For a day trip way outside the city limits, head to Rockford and check out Anderson Japanese Gardens , one of North America’s premiere Japanese gardens. The authentic and tranquil 12-acre sanctuary includes streams, waterfalls, koi-filled ponds, and more for its guests to explore. Keep in mind that pre-paid, timed-entry reservations are now required.

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5 Incredible Illinois Day Trips You Can Take By Train

chicago day trips by train

Amanda Glandon

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The next time you have a free day or weekend and you want to plan something new and exciting, we have the perfect options. For anyone searching for “train trips near me” in Illinois, there are several options. There are some unique train trips in Illinois that can be completely round trip and take you to different parts of the state that maybe weren’t an option otherwise. Amtrak train routes spread across Illinois allow for many opportunities for fun and exciting day trips. Grab your tickets at the nearest train station, hop on, and explore our beautiful state! Here are some suggested train rides in Illinois you can take:

chicago day trips by train

chicago day trips by train

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chicago day trips by train

chicago day trips by train

Don’t you just love train travel? If you’re ready to start planning your train rides in Illinois, then head to the Amtrak website to create your day trip itinerary. It’s as easy as entering in your starting location and visiting destination, and voila!

How do these incredible scenic train rides in Illinois sound to you? What trip are you planning to take first? Let us know in the comments section!

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

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Where can I go on one tank of gas in Illinois?

You can go to many places on one tank of gas in Illinois. Some destinations include:

  • The serene countryside of Arcola
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Check some of the other attractions to visit around the state on one tank of gas .

What are the best road trips through Illinois?

Some of the best road trips in Illinois include:

  • A road trip to Illinois' waterfalls
  • The Great River Road
  • A road trip to see some of Illinois' most charming small towns

Check out some of the best weekend road trips in Illinois as well as these 10 unforgettable road trips in Illinois .

Can I go for a train ride in Illinois?

Yes, you can go for a train ride in Illinois. We’ve talked about destination-focused train trips in Illinois, but here are some other types of train rides you can take:

  • A magical Polar Express Train ride that comes around every Christmas. This train takes guests on a journey into the famed holiday storybook complete with characters, hot chocolate, and music!
  • For anyone looking for a bit of a scare, the Halloween Train Ride at the Fox River Trolley Museum is also a fun experience. 

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How to get from O'Hare International Airport to downtown Chicago

Caroline Tanner

Chicago is arguably one of the greatest cities in the world. If you have never been to Chicago, stop reading this and book a trip now. Once you do that, return to read this guide, so you can know how to access this city.

To start, know that the Windy City has two airports — O'Hare International Airport (ORD) in the northwest suburbs and Midway International Airport (MDW) on the city's South Side.

The two airports are approximately 30 miles apart. The majority of international flights are serviced by ORD, with 100 daily flights to 60 cities abroad .

If you are flying into ORD, this guide is for you; here are the fastest ways to get from ORD to the city of Chicago.

chicago day trips by train

Visitors can commute across Chicago via the Chicago Transit Authority 's elevated train, called the L, which provides service directly to and from ORD via the Blue Line. However, if you have a lot of checked luggage, note that the trains do not have luggage racks, and some of the stations are only accessible via stairs.

Depart from : Catch the Blue Line directly from Terminal 1, 2 or 3, or via a free airport shuttle train from Terminal 5.

Possible destinations : From ORD, you can take the Blue Line to and through downtown en route to Forest Park or UIC-Halsted, depending on the time of day.

Hours of operation : The L runs 24 hours a day between ORD and Forest Park, with overnight service operating approximately every 15 to 30 minutes.

Transit time : It will take you roughly 40 to 45 minutes to get downtown via the Blue Line.

Estimated cost : A single-trip Ventra pass from ORD costs $5, is valid for up to three rides within two hours of use and can be purchased at the O'Hare station. You can also buy a three-day pass that includes unlimited rides for $15. Note that you can use contactless payment (contactless bank cards and Google, Apple or Samsung Pay), cash or a credit card to pay for your pass. Reduced rates from O'Hare for students younger than 12 are available for 75 cents during designated student fare hours and $1.25 at all other times.

chicago day trips by train

Taxis are available from the airport and can accommodate most groups with sedans and larger-size cabs.

Depart from : There are taxi stands outside of baggage claim on the lower level at each terminal and the inner commercial lane at Terminal 5.

Possible destinations : You can use taxis to reach downtown Chicago and its suburbs.

Hours of operation : Taxis are available 24 hours a day.

Transit time : When using a taxi, expect the trip to take between 25 and 90 minutes, depending on your destination. Trips to downtown neighborhoods, including Streeterville, River North and Gold Coast, take roughly 30 to 40 minutes.

Estimated cost : Cab companies offer a flat rate for rides downtown , which is a straight meter fare plus one-half of the straight metered fare plus a $4 airport departure tax. From ORD to the city, cabs are approximately $40. It's standard practice to tip cab drivers in Chicago, so consider factoring this into your budget, too. Generally speaking, a 20% tip should suffice.

Uber and Lyft

chicago day trips by train

A popular (albeit pricey, depending on the time of day) way to get from O'Hare to central Chicago is via ride-hailing services like Uber and Lyft.

Depart from : Specific Uber and Lyft pickup areas can be found in Terminal 2. They're located on the upper level between doors 2A and 2E.

Waiting areas are color-coded as follows: Black Zone A, Black Zone B, Orange Zone C and Green Zone D. Passengers should proceed to the colored zone serving as their designated pickup location for both Uber and Lyft.

Once booked, your respective app will tell you which pickup area to use to meet your car. Although you can book a ride via a ride-hailing service upon deplaning, your car will not be reserved until you reach the assigned pickup area.

Possible destinations : You can use services like Uber and Lyft to get to downtown Chicago and its suburbs from O'Hare.

Hours of operation : Ubers and Lyfts are available 24 hours a day.

Transit time : Rides will take between 25 and 90 minutes, depending on your chosen destination. Trips to downtown neighborhoods, including Streeterville, River North and Gold Coast, usually require roughly 30 to 40 minutes to reach.

Estimated cost : From ORD to the city, ride-hailing services generally charge between $35 and $60, depending on the destination. Know, though, that surge pricing during busy periods like rush hour can cause prices to climb to $140.

Metra, shuttles and coaches

Various private shuttle and limo services, including Go Airport Shuttle , can also be booked from the airport. This service starts at $75 for trips to downtown Chicago.

Alternatively, Peoria Charter operates a bus from Terminal 2 to the city center twice daily, with tickets costing $50 for roughly an hour ride.

While there is a Metra station for commuter rail services called the O'Hare Transfer stop , most locals do not advise taking it, as the schedule is random and there is no on-site agent should you need help.

Bottom line

chicago day trips by train

Having commuted downtown from O'Hare more times than I can count, I can confirm that each way — the train, cabs and ride-hailing services — can take around the same length of time, and that time will depend on the time of day and traffic, or any service disruptions for the L.

The only real guarantee is that the L will be the cheapest option, but as they say, time is money. Regardless of the traffic you sit in, I promise the ride is worth it.

Related reading:

  • Sky-high luxury: A review of the new St. Regis Chicago
  • Chicago's Midway Airport to get its first lounge
  • What it's like staying at the historic Chicago Athletic Association, part of Hyatt's Unbound Collection
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    Find recommendations and ideas on the best day trips from Chicago, Illinois, with pictures, details, and travel tips. See the best places to visit outside Chicago, based on your interests.

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    Amtrak Hiawatha Chicago day trip: Chicago is indisputably the heart of American railroading. Amtrak NPCO (non-powered control unit) No. 90200, former EMD F40PH No. 200, carries the markets of a northbound Hiawatha train having just crossed the Menomonee River on its final approach to Milwaukee Intermodal Station.

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  22. 10 Chicago Summer Day Trips

    The Forge Outdoor Adventure Park in Lemont. Photo by Jeff Anderson. 29 miles from Chicago. For those looking for a Chicago-area day trip filled with adventure, The Forge: Lemont Quarries is a one-of-a-kind destination perfect for families and friends alike. This new adventure park, built on 300 acres of land in Lemont, Illinois, includes ...

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    Possible destinations: You can use taxis to reach downtown Chicago and its suburbs. Hours of operation: Taxis are available 24 hours a day. Transit time: When using a taxi, expect the trip to take between 25 and 90 minutes, depending on your destination. Trips to downtown neighborhoods, including Streeterville, River North and Gold Coast, take ...