Top Chicago Crime Tours

Chicago's Original Gangster Tour by Bus

4.7

(129)

1 hour 45 minutesFree Cancellation

from $48

Chicago Architecture and True Crime Tour

(366)

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

from $35

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

(54)

1 hour 30 minutesFree Cancellation

from $35

4.7

(410)

Chicago Mobs and Haunts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

from $34

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

4.8

(485)

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

from $55

176

Original Chicago Prohibition Bus Tour

4 hoursFree Cancellation

from $55

Chicago Murder Mystery Tour

(734)

2 hoursFree Cancellation

from $35

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!

Chicago River Ghost & Dark History Night Cruise

4.0

(110)

1 hour 30 minutesFree Cancellation

from $46

176

Walking Prohibition Tour

3 hours 30 minutesFree Cancellation

from $45

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.

Gangs and Mobsters Crime Tour at Chicago

(2)

1 hourFree Cancellation

from $26

644

Chicago Gangster History Walking Tour of River North

2 hoursFree Cancellation

from $40

Price varies by group size

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)

1 hourFree Cancellation

from $59

Per group

Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Matt_W, Apr 2026

Unique, interesting tour

Excellent storytelling. The guide and tour owner Andre is passionate, knows history, and cares about his guests enjoying the tour. It was a fun combo of haunts and crime. The only negative was how the time flew by because Andre was so entertaining. Highly recommended.

Chicago Architecture and True Crime Tour

Markie_B, Mar 2026

David was the best!

We needed something to do for a couple hours until we had to head to the airport. We looked into one of the boat architecture tours, but sadly, they were all booked. This ended up being an amazing thing, because we REALLY enjoyed our tour and time with David. David is clearly passionate about the information he presents and it was lovely spending time with him. The buildings we viewed were beautiful and it was great to place factual information into how things came to be. I would recommend to anyone and the true crime information was a really fun addition to the 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

Victoria_V, Sept 2025

Chicago mobster style

Maria was our tour guide. We boarded the bus to a flapper, dressed young Chicago woman who had an amazing sense of humor, witty, and was an excellent historian. We absolutely loved our tour and have not stopped talking about it. When other friends of mine come to Chicago, I definitely plan on taking them on this tour.