Top Chicago Crime Tours

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

(482)

from $35

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.

(60)

from $35

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

4.7

(156)

from $48

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

1 hour 30 minutesFree 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!

(287)

from $35

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

1 hour 30 minutesFree Cancellation

4.1

(155)

from $46

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

(503)

from $55

Chicago Mobs and Haunts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(443)

from $34

Original Chicago Prohibition Bus Tour

4 hoursFree Cancellation

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

(3)

from $55

Chicago Gangsters and Ghosts Walking Tour

Chicago Gangsters and Ghosts Walking Tour

Chicago Murder Mystery Tour

4.7

(40)

from $38

Likely to Sell Out

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.

(750)

from $35

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

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

1 hourFree 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 $59

Per group

Chicago True Crime and Gangsters Tour

1 hour 30 minutesFree Cancellation

3 hours 30 minutesFree Cancellation

(9)

from $35

Walking Prohibition Tour

4.5

from $45

Chicago Gangster History Walking Tour of River North

Price varies by group size

(1)

from $40

Chicago Haunted Buildings Walk inside 6 Haunted Skyscrapers

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

from $55

Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Sean_N, Jun 2026

Andre, was great! Stories...

Andre, was great! Stories were fun and entertaining. Very knowledgeable about Chicago too! Definitely recommend. Only suggestion is increase the volume for Andre somehow. The city is loud at times with the train passing by especially, and it can be hard to hear him. With that said it was maybe 10% of the time it was an issue. Still 5 stars!

Chicago's Original Gangster Tour by Bus

Jill_J, Jun 2026

It Was A Hoot!

Marie did such a great job narrating the tour. She was an absolute fount of knowledge regarding all the gangsters and mob bosses in Chicago. She played the music of the times, dressed in the traditional costume and just loved her accent! “Chi-cah-go!” 😄 I would highly recommend going on this tour - it takes you places the regular busses don’t go. 5 stars!

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!