Top Chicago Crime Tours

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(394)

from $35

Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

(196)

from $35

2 hoursFree Cancellation

Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.

(49)

from $35

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

4.7

(134)

from $48

Stop off the bus at Chicago Landmark Building with Prohibition Era History

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

4.8

(488)

from $55

Skip the guesswork and discover the real haunts of Capone, Dillinger, and The Outfit on a walking tour that then also you shows how those same streets become movie stars. Walk the city corners seen in *The Untouchables* and *Public Enemies,* and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both.

Chicago Crime and Movies Tour

Chicago Mobs and Haunts Walking Tour

(58)

from $35

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(417)

from $34

Likely to Sell Out

Chicago Murder Mystery Tour

2 hoursFree Cancellation

3 hours 30 minutesFree Cancellation

(738)

from $35

Walking Prohibition Tour

4.5

from $45

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner detective on this immersive, self-guided scavenger hunt through Chicago’s Loop! Step back to 1923 as you gather clues, solve a murder mystery, and unlock secrets of Prohibition-era Chicago. Your group receives a mystery kit, then follows a story-driven trail at your own pace—no app required. Observe real landmarks and hidden clues as you work together, making this ideal for friends, families, and groups seeking a hands-on, flexible adventure. The perfect blend of history, teamwork, and local intrigue in the heart of Chicago.

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

1 hourFree Cancellation

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

(1)

from $59

Per group

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most notorious mobsters and gangs. Immerse yourself in the rich history of the Windy City as you stroll through its vibrant streets, where the echoes of a century of Mob activity intertwine with the modern cityscape. Traverse the iconic Michigan Avenue, once a hub of illicit operations masterminded by the infamous Al Capone, and uncover the hidden secrets of the past that now lie beneath the surface of changing demographics and contemporary establishments. Brace yourself for chilling tales of mob hits and ongoing underworld dealings, as you unravel a dark and compelling narrative that still resonates through the streets today.

4.1

(119)

from $46

Gangs and Mobsters Crime Tour at Chicago

Gangs and Mobsters Crime Tour at Chicago

1 hourFree Cancellation

Chicago Gangster History Walking Tour of River North

(2)

from $26

2 hoursFree Cancellation

Price varies by group size

(1)

from $40

Original Chicago Prohibition Bus Tour

4 hoursFree Cancellation

Our goal is to disturb and unsettle you of whatever assumptions you may have about Chicago. We do so with our entertaining and brilliantly researched experiences, that highlight the historic gangster past of Chicago, and also shares the hidden beauty, natural wonders, and cultural highlights of America's third-biggest city. Guests walk away more historically oriented travelers, with a reason to visit Chicago again.

(1)

from $55

Special Offer

Chicago True Crime and Gangsters Tour

Chicago Crime and Movies Tour

from

$35

$28

Top Attractions in Chicago

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What are people saying about Chicago

David_B, May 2026

André was a fun and...

André was a fun and humorous guide with lots of historical and contemporary knowledge of the Chicago crime and movie events from the last 250 years. He even pulls off a Harrison Ford accent! The tour is a casual walking tour through downtown Chicago and stopping at many points of interest and the stories behind them.

Chicago Architecture and True Crime History Tour

Okeema_P, May 2026

Fantastic tour, 10/10!

Roan was our tour guide and he did a fantastic job. The meet up was easy to find, Uber was able to drop us off right in front of Palmer House and we saw a small group and assumed “this must be it”. I really enjoyed learning some of the “crime story” history of Chicago, it was truly fascinating. As visitors to Chicago, we had explored downtown prior to the tour however, the tour really provided a different experience that made “downtown” seem like a “different” downtown as we learned some of the architectural history. The stories were told with such passion that you would have thought Roan was there; he knows his stuff! My daughter, a senior in college, who enjoys history had heard some of the history and shared with me after about a particular story, “I’ve heard that story before (I won’t spoil it…lol), but I’ve never heard it told like that; I really enjoyed it”. Our tour was a small group of 4 and at times it was hard to hear due to the “city noise”, I imagine if we were larger the guide would have used a mic; it worked for just 4, we could gather closer when needed. I would absolutely recommend!

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Carol_C, Apr 2026

What are you waiting for? BOOK This TOUR!!

We had a great time! My son (17) and I are true crime and ghost junkies and Andre’s tour did not disappoint. He is an amazing storyteller and guide. Great information along with a true insight to the city. Walking was the way to go. We both would highly recommend the tour. 90 min, easy walking and it flew by all ages would enjoy. Why are you still reading this review… you should be booking your tour!🤩

Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

Anonymous, Nov 2025

Very enjoyable tour!

Very enjoyable tour to do. Our guide, Scott was very knowledgeable and shared many old stories about the area. We went along the river walk for a bit and were in and out of hotels and restaurants spotting pieces of Chicago history. I highly recommend this tour!

Chicago Mobs and Haunts Walking Tour

Terrance_T, Oct 2025

10/10 Tour + Guide

had Alyssa. She was a great guide. Very knowledgeable and excited to share the information. She was very personable as well. Tour stuck to the theme very well and there were plenty of interesting facts that I was never aware of. The history of Chicago is very rich. Would 100% recommend to other tourists or people who love history. Plenty of different people in my tour group, from couples to people with kids. Alyssa was welcoming to all. Ran into sooo many problems on my trip in Chicago, this tour was by far the highlight of my trip. I will definitely be doing something similar whenever I come back.

Chicago's Original Gangster Tour by Bus

Ann_S, Oct 2025

What an adventure!

Marie was great. We enjoyed the tour very much. She was informative and funny. Very impressive. We were visiting from Arizona and when friends gave me the list of tours this one caught my attention as my parents were born in that era and my dad was an Indiana State trooper in the 40’s. I will recommend this adventure to anyone I know is visiting Chicago.