Top Chicago Crime Tours

Chicago's Original Gangster Tour by Bus

4.7

(126)

1 hour 45 minutesFree Cancellation

from $48

Chicago Architecture and True Crime Tour

(342)

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

from $35

4.8

(482)

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

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

(49)

1 hour 30 minutesFree Cancellation

from $35

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(93)

1 hour 30 minutesFree Cancellation

from $35

Chicago Murder Mystery Tour

(731)

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

(106)

1 hour 30 minutesFree Cancellation

from $46

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

(1)

1 hourFree Cancellation

from $26

643

Chicago Gangster History Walking Tour of River North

2 hoursFree Cancellation

from $40

Price varies by group size

176

Original Chicago Prohibition Bus Tour

4 hoursFree Cancellation

from $55

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 $23

Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Gwendolyn_S, Jan 2026

Chicago’s history comes alive!

What a gem of a tour. The host was animated, funny and told great stories about the gangsters and ghosts of Chicago. The tour was well designed and made the city’s history come alive. My teenage boy, who has never been here, loved all of it! He indicated that “it was a great way to see the city! 5 stars”

Chicago Architecture and True Crime Tour

Lauren_S, Dec 2025

This tour was fascinating...

This tour was fascinating and Joseph was such an engaging tour guide! A majority of the tour was spent inside looking at interior architecture, with brief walks outside to get to the next destination (much appreciated on this 10 degree winter day!) Would definitely book again

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, Sep 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.