Top Chicago Crime Tours

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(388)

from $35

1 hour 30 minutesFree 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.

(185)

from $35

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

4.7

(133)

from $48

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

2 hoursFree Cancellation

Chicago Murder Mystery Tour

(47)

from $35

Likely to Sell Out

2 hoursFree Cancellation

Chicago Night Crimes Tour by Bus

(738)

from $35

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

2 hours to 2 hours 30 minutesFree Cancellation

4.8

(488)

from $55

Chicago Mobs and Haunts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(413)

from $34

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

1 hour 30 minutesFree Cancellation

3 hours 30 minutesFree Cancellation

(57)

from $35

Walking Prohibition Tour

4.5

from $45

Chicago River Ghost & Dark History Night Cruise

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

1 hour 30 minutesFree Cancellation

4.1

(117)

from $46

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

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.

(1)

from $59

Per group

Gangs and Mobsters Crime Tour at Chicago

Gangs and Mobsters Crime Tour at Chicago

1 hourFree Cancellation

Original Chicago Prohibition Bus Tour

(2)

from $26

4 hoursFree Cancellation

Chicago Gangster History Walking Tour of River North

(1)

from $55

2 hoursFree Cancellation

Price varies by group size

(1)

from $40

Top Attractions in Chicago

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What are people saying about Chicago

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

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 Mobs and Haunts Walking Tour

Sven_Z, Mar 2026

Great experience - not only for visitors.

Bryson is a great guide who enthusiastically engaged in riveting stories about Chicago. Living in Chicagoland for 20+ years, this experience is not only for tourists and visitors - you learn about the hidden sides of Chicago. I am somewhat glad that I didn't live in the 1920's Chicago.

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'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.