gangster chicago tour

The Original Chicago Gangster Tour

Quick Details

• Hour Glass Duration: 2 Hours

Visit Chicago’s Most Infamous Locations on Our Gangster Tour

We are  Untouchable Tours –   Chicago’s  Original  Gangster Tour.  We have been providing a top-notch educational and historically accurate tour for over 35 years!

Our guides present an accurate account of the crimes and activities that were going on in Chicago during the 1920’s and ’30’s (Prohibition). You will hear the exploits of Capone, Moran, Dillinger and the rest of the boys on this unforgettable Chicago crime tour ! Guests remain on the bus for the duration of the tour. Some sites included are the St. Valentine’s Day Massacre, the Biograph Theatre, and the Holy Name Cathedral. 

The tour is educational yet fun. Our Gangster Guides are professional actors and bring the world of Prohibition and the 1920s to life. Our Untouchable Tour Gangster Guides take on the persona of gangsters and mobsters and will bring the tour to life!

Meet our Gangster Bus on the sidewalk of Clark Street, between Ohio and Ontario, in front of the McDonald’s.

Guests should arrive 10 minutes before the scheduled tour time and will be checked in by the tour guide. Tours will leave promptly at tour time.

Guests remain on the bus for the duration of the tour.

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The 9 best crime tours of Chicago

Explore the seedy underbelly of Chicago on these fascinating crime tours

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Chicago is well known for its towering architecture, amazing restaurants  and beautiful beaches , but the city also has a notorious history of Prohibition-era organized crime and violence. Some of Chicago’s most beautiful streets have dark pasts, and you can explore the oftentimes grisly history on a Chicago crime tour. Guides unearth the city’s darkest stories, and some of them even make stops at local restaurants and bars to help set the scene. While the tours may be a bit eerie, some can be experienced on your own schedule, whether in-person or virtually. Experience Chicago's history hidden in plain sight on the best Chicago crime tours.

RECOMMENDED: Check out the full guide to the best Chicago tours

This article includes affiliate links. These links have no influence on our editorial content. For more information, see our   affiliate   guidelines .

Been there, done that? Think again, my friend.

Best Chicago crime tours

1.  chicago crime and mob tour.

Follow in the footsteps of infamous gangsters like charming bank robber John Dillinger and Polish mobster Hymie Weiss on this bus tour. You’ll hear stories about the who’s who of Chicago organized crime, drive by a few murder locations and spot the historic courthouse where many criminals were thrown in the clink. 

Time Out tip:  Brush up on your crime knowledge for the post-tour quiz. 

2.  Untouchable Tours' original gangster tour

For more than 30 years, Untouchable Tours has been driving tourists back and forth across the city to see Chicago's more unconventional sights, including the staircase in front of a church that’s covering up bullet holes, and the empty lot where the St. Valentine’s Day Massacre took place. The two-hour tour features guides that take on the persona (and snappy garb) of ’20s gangsters. Guides tell the tales of prohibition-era Chicago and what it was like when gangsters like Al Capone, Bugs Moran and Hymie Weiss walked the streets.

Time Out tip:  One to book in advance for. 

3.  Gangsters and ghosts tour in Chicago

The towering skyscrapers and shining facade of Cloud Gate might make the Loop seem glitzy and glamorous, but it was once a hotspot for vice. In the ’20s and ’30s, this nabe was the epicenter of bootlegging and gangbanging in Chicago. Take a walking tour through the area to spy speakeasies, secret underground tunnels and maybe even a ghost or two.

Time Out tip: The meeting point is just outside the Wyndham Hotel – take that as our accommodation suggestion. 

4.  Vice, crime and gangsters in Chicago: A self-guided audio tour

There are endless upsides to taking tours of a city, but there are downsides as well—most notably, not being able to explore at your own pace. That’s not the case with the self-guided Vice, Crime and Gangsters in Chicago tour. The 31-stop audio tour starts at the Dusable Bridge and winds its way through notorious locations in the Loop and River North, including Chicago’s first vice district and the site of the Lager Beer Riot. It’s narrated by professor, urban historian and former journalist Richard Junger.

Time Out tip:  If you want to get familiar with your guide before the tour, have a skim-read of the books he's written on Chicago history. 

5.  Chicago night crimes tour

See the sites of grisly killings under the dark of night on this evening bus tour. You’ll visit the Biograph Theater where Dillinger met his end, the site of the St. Valentine’s Day Massacre and other infamous locations. The bus even stops at a few historic watering holes like Harry Caray's so you can raise a glass to the city's dearly departed criminals.

Time Out tip: Don't worry about trying to snap pics from the window of the bus – photo stops will be granted. 

6.  Lincoln Park hauntings ghost investigation tour

On the surface, ghost tours and crime tours are two separate entities. But how does one become a ghost? Death. And how does someone’s death become notable enough to end up on a tour? It’s got to have some sort of criminal element, right? This ghost investigation tour is led by a paranormal investigator who takes guests through some of the eeriest locales in Lincoln Park, including the site of the St. Valentine’s Day Massacre. It also offers an opportunity to use paranormal activity-detecting equipment to help you determine if you just saw a ghost or a very exhausted DePaul student.

Time Out tip:  Keep your eyes peeled for the Victorian woman in white at Lincoln Park Zoo. 

7.  Private Al Capone gangster tour

Al Capone’s trademark look – thick eyebrows, jaunty hat, heavy overcoat and a cigar hanging from his lips – became the basis of the stereotype of the mafia man. Capone got his start in New York as a member of the Five Points Gang before founding the Chicago Outfit and wreaking havoc on the Midwestern city. Follow in his nefarious footsteps on this tour around the city in a private town car – in true mafioso style.

Time Out tip: Get a team of five together to get the best value group ticket. 

8.  Private Chicago Mafia and Blues Evening Tour

After a long night of making dirty deals and plotting the downfall of their enemies, Chicago mobsters used to unwind with some booze and live music at a mafia-friendly bar. You’ll do the same on this private guided tour that hits several historic landmarks before stopping for a drink at a bar formerly owned by Capone himself.

Time Out tip:  Plan this tour around a big night out, as it's a great way to get the party started before hitting the town when everyone's parted ways. 

9.  The Devil in the White City Tour

In addition to a thriving mob community, Chicago was also home to one of the country’s first known serial killers: H. H. Holmes. The insurance scammer and con man lured hundreds of people to the three-story hotel that would later be known as the Murder Castle: a labyrinth of trap doors, peepholes, dead-end stairways, gas chambers and crematorium that he used to murder his victims and dispose of their remains. To this day, authorities still don’t know how many people he might have killed. Learn the disturbing facts of the case on a Weird Chicago walking and bus tour.

Time Out tip: There's a restroom on board – always a win. 

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Chicago Crime & Gangster Tour

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Free Chicago Walking Tours Chicago Crime & Gangster Tour takes you on an incredible journey through Chicago's storied past. You will learn how the Chicago Mafia came to power and visit some well-known and not-so-well-known Chicago Mob hangouts all while seeing the beautiful River North and Loop neighborhoods. And the best part - this Chicago Crime & Gangster tour is FREE!

The Characters

You have heard all of the household names before - Al Capone, Boss Dean O'Banion, George "Bugs" Moran, The North Side Gang & "Machine Gun" Jack McGurn. But do what the Beer Wars was? Or where the infamous Florist Shop was located? Let our resident Crime and Gangster expert tour guide take you on a walk through Chicago's storied criminal past on this fun and educational walking tour through River North and Chicago's Loop.

Starting at the picturesque Historic Old Water Tower at the corner of Chicago & Michigan Avenue our Chicago Crime & Gangster tour will clear the air on what really went down in Chicago during the roaring 20s and after.

Wind your way through the River North area learning about the multiple gangs and their leaders that were vying for a piece of the prohibition pie. Stops at Marina City Towers and the Lasalle Street Bridge will help explain how all of these characters crossed paths and shaped the future of Chicago.

And is there a more fitting end to the tour than Chicago's Federal Plaza - a place that represents law and order. The site of Al Capone's trial and conviction and now home to one of Chicago's most iconic pieces of public art - Calder's Flamingo.

Meeting Point:  Old Water Tower - Corner of Chicago & Michigan Avenue.  Google Maps

Distance:  2.1 miles walking distance

Time:  2 hours from start to finish

Cost:  FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip .

What you will see: 

• Old Chicago Water Tower
• Holy Name Cathedral
• Levi's Store - the former location
• Marina Towers
• Lassie Street Bridge
• Chicago Crime Commission Headquarters
• Federal Plaza

Stories you will be told: 

• The start of gangs in Chicago
• Boss Dean is shot at the Florist Shop
• The Story of "Machine Gun" Jack McGurn
• The Office gets bugged
• How the business changed from bootlegging to loans & gambling
• Peace talks break down
• Al Capone's Trial & Conviction

More Free Chicago Walking Tours

We know you will love the Chicago Crime & Gangster tour, so why not plan ahead and book another tour? If your group is larger than 6 people contact us regarding a Private Chicago Walking Tour .

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• Free Chicago Walking Tour Experience
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Offering bus guided and walking tours rooted in Chicago’s most notorious era.

Visit the speakeasies that made the famous, infamous. Become a "scofflaw" on our tours that tell stories of gangsters, politicians, and beyond in the spaces where it happened.

#1 Prohibition Tour In Chicago

Customers love us.

What a great tour to learn the history of famous Chicago speakeasies while enjoying a few drinks a long the way! The history given was thought provoking, we are delighted we booked the tour – it was the highlight of our recent visit to Chicago.

Sonia, International Traveler

From The Blog “The Hush” (Shh Speak Easy)

A Prohibition Conspiracy Theory That Might Actually be True?

A Time To Drink

What do you write about when it’s time to start the new blog for your new company do you write about the idea behind the company maybe, do you write about the start up process maybe, the research process  read more.

A Toast to the Prohibition Movement and Its Epic Failures

Chicago Prohibition Gangster Tour

Chicago's Underworld Revealed!

Quick Details

• Users Ages: 10+ years old
• Hour Glass Duration: 2.5 hours
• Calendar Days: Various Dates

Explore Chicago’s Gangster History

This in-depth, two-and-a-half-hour private bus tour immerses you in Chicago’s Prohibition Era crime history. You visit notorious sites associated with Al Capone, his North Side rivals, and John Dillinger, including where the infamous St. Valentine’s Day Massacre took place, where Dillinger was killed, and the locations of other gangland hits and near misses.

Your tour guide is John Binder, author of Al Capone’s Beer Wars and The Chicago Outfit and the consultant on numerous organized crime documentaries. He shares his vast knowledge on the subject and answers all your questions throughout the tour.

This luxury bus tour involves no walking, but we do make a few stops where you are welcome to exit the bus to get a closer look. Contact John at [email protected] to arrange a tour!

Related Tours

• Twice per Day
• Hour Glass 2.5 hours
• Users 10+ years old

Oak Park & River Forest Gangster Tour

Immerse yourself in the history of organized crime in Chicago from Prohibition until the 1990s, focusing on the lives and careers of many of Chicago’s most famous gangsters.The “There Goes The Neighbor Hood” tour focuses on gangster history in Oak Park and River Forest.

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Chicago: Gangsters and Ghosts Tour

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Energize Your Kayak Adventure! Get a 10-Pack at a Special Rate! Act Now!

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GHOSTS AND GANGSTERS TOUR

With the 1848 arrival of the railroad and the Illinois and Michigan Canal to Chicago, the city accelerated its unprecedented boom. In lockstep with the growth of business and speculation came the explosion of the city’s infamous underworld.

Join us in the evenings as we offer our unique take on writer Nelson Algren’s “Hustlertown, USA”. Kayak down the Chicago River with us as the sun sets into twinkling darkness and experience the legacy of our nefarious gangsters. Night time paddling is beautiful – come enjoy the scene!

On this tour, you will learn about the city’s early Wild West reputation, how one man rose from poverty to become the most powerful man in our city’s history, how one area of the river purportedly became haunted, why everyone in nascent Chicago feared a man the size of a child, and all about the larger-than-life Italian crime lineage including the likes of mobsters Jim Colosimo, Johnny Torrio, and, of course, Al Capone.

TOUR DETAILS

• Duration On-water: ~2 hours Orientation/Launch: ~25 minutes
• Ticket Price $65 per adult $45 per child (under 16)
• Options Children small enough to fit in child seat are free (usually 2-4 years old). Parental discretion is advised for this tour.
• Inclusions Single or double kayak (choose upon arrival), life vest, paddle, guide(s), safety orientation, paddling lesson
• Attire Comfortable, water-friendly clothing and shoes are suggested, as you will likely get wet. Denim not recommended. Dress for the weather on the day of the event.
• Weight limits Single kayak - 275 lbs (approx.); Double kayak - 500 lbs (approx.)
• Private Option If you are interested in this tour, but are unable to go at one of our scheduled times, send us an email at [email protected] to request a private or semi-private tour!

TOUR ITINERARY

Orientation.

At the beginning of each tour, we teach the basics of flat water kayaking and brief our guests on river safety in a 10 minute orientation session.

PADDLE ADVENTURE

We paddle as a group to a series of locations that we have chosen for the view, safety, and their historical significance. Our guides make sure everyone stays safe from boat traffic and obstacles.

GANGSTER TALES

This tour covers many sordid personalities; from the little-known gangster bosses of the nineteenth century to the infamous lineage of Italian mobsters. Alliances form and dissolve just as quickly as different factions fight for their share of power. We present the good and the bad as we discuss the kings and queens of vice of Chicago’s past.

Find yourself floating on the brightly illuminated surface of the river as it reflects the twinkling, golden lights of the city above. Enjoy fantastic photo opportunities as the day slips into darkness and the ghosts of Chicago's gangster past awaken!

Take some final snapshots of the gorgeous nighttime skyline before a short paddle back to the dock, where we assist everyone out of the water. Numerous dining options in the area are still open if you are feeling hungry!

• Susan A: We decided to do their Shady Chicago: Ghosts and Gangsters tour on our last night in town...and we were so glad we did...The weather was perfect, the staff was incredibly friendly and knowledgeable and the tour was the perfect length. To be on the water at night with the lights of Chicago all around you is truly worth the price of admission. Read full Testimonial
• ILroadies: The location of the dock is perfect. Overall great experience, we will definitely return for another kayak excursion... Read full Testimonial
• Jessica C: Kayaking was a lot of fun! Very friendly tour guide and all levels of kayakers welcome and comfortable... Read full Testimonial

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Chicago Gangsters and Ghosts Tours

Chicago Tours | Gangster Tour and Ghost Tour

Gangster Food Tour

Two Tours Daily at 11:15 am and 1:30 pm.

Immerse yourself in the flavor and history of Chicago’s most innovative and violent past.

Savor prime steak, indulge in Chicago’s own deep dish pizza and relish the world renowned Chicago Hot Dog. All while exploring the streets walked by Al Capone’s fiercest enemies and closest associates. Don’t miss seeing the tunnel gangsters emerged from after escaping jail or the bullet holes left behind after one of Prohibition’s most brazen assassinations.

When: Daily at 11:15 am and 1:30 pm (please arrive 10-15 min before tour time)

Where: Chicago’s River North, magnificent mile and Gold Coast neighborhoods

Meeting Location: 71 E Wacker Drive – outside the Royal Sonesta Hotel & Hoyt’s Tavern

Ending Location: 822 N State St.

Length (Time): Approximately 2 hours

Length (Distance): Approximately 1.5 miles with frequent stops.

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Lighthouse Inn in Cedar Rapids celebrates 112 years of business

CEDAR RAPIDS, Iowa (KCRG) - The Lighthouse Inn Supper Club in Cedar Rapids celebrated its 112 year anniversary this weekend with an antique car show and a call back to some of the history that’s made the restaurant what it is today.

The Lighthouse Inn restaurant was once an actual inn off the original Lincoln Highway, which hosted famous gangsters like Al Capone.

”So you had a lot of traffic from Chicago, especially during prohibition,” said Jason Cullum, one of the event’s hosts.

On Saturday, the restaurant honored its storied past with a special menu some of its famous patrons used to enjoy.

Tommy Terrill won the car show, and his unique presentation drew quite a few glances.

”You don’t just go out and buy one, you have to build it to match your personality,” Terrill said.

Terrill said car shows like this help get new eyes on the hobby so some older rides don’t go forgotten.

”You go to the car shows, and a lot of the people who have cars like this... are older,” Terrill said.

The car show isn’t just keeping the history alive, it’s also helping support some antique car owners.

”So we’ve been reached out for unique events for stuff like that, so that’s another cool thing about these is you get out here and people like it and they ask you to do stuff for them,” said Justin Bascom, a car show contestant.

Beyond getting to show his car off, Terrill said he’s just happy to see the little pieces of history everybody else brings in too.

”I’ve never been to a car show that I didn’t have fun at.”

Copyright 2024 KCRG. All rights reserved.

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