Top Chicago Crime Tours

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

4.7

(144)

from $48

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

Chicago Architecture and True Crime History Tour

(52)

from $35

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

Chicago Night Crimes Tour by Bus

(437)

from $35

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

2 hours to 2 hours 30 minutesFree Cancellation

4.8

(492)

from $55

Chicago Mobs and Haunts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(430)

from $34

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.

Chicago True Crime and Gangsters Tour

1 hour 30 minutesFree Cancellation

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(1)

from $35

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!

(248)

from $35

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

1 hour 30 minutesFree Cancellation

4.1

(130)

from $46

Likely to Sell Out

Chicago Murder Mystery Tour

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.

(740)

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

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

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 his 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". You will also enjoy a short rest stop at a famous former gangster hangout. 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 with a visit to the Congress Hotel, one of the most haunted places in Illinois.

(2)

from $26

Chicago Gangsters and Ghosts Walking Tour

Chicago Gangsters and Ghosts Walking Tour

Original Chicago Prohibition Bus Tour

from $38

4 hoursFree Cancellation

3 hours 30 minutesFree Cancellation

(3)

from $55

Walking Prohibition Tour

4.5

from $45

Chicago Gangster History Walking Tour of River North

Price varies by group size

(1)

from $40

Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Lesley_S, May 2026

This was a fun combo of...

This was a fun combo of architecture tour, ghost tour, and crime tour. I was in town for a road race, and was looking for a way to see part of the city. We learned about some of the city’s historical buildings and what events happened at each one. These events ranged from the 1800s to modern times. A note based on the tour description, we didn’t see any speakeasies, but learned about a couple famous ones.

Chicago Architecture and True Crime History Tour

sailelan, May 2026

We booked it last minute...

We booked it last minute and we actually like the 7 pm tour because we flew in late and we were happy to get a tour in. We truly enjoyed all the fun facts about Chicago. Absolutely love walking around as sun was sitting, it makes Chicago more magical. Joseph our guide was helpful answering all the questions and he was our very own photographer. Definitely will recommend to friends and family.

Chicago's Original Gangster Tour by Bus

DulceMaria_D, May 2026

So gangsta! ⭐️⭐️⭐️⭐️⭐️

Honestly, this exceeded my expectations. I’m a Chicagoan and it felt like I experienced a visit to my own city. It was two hours of “wow” with orchestrated 1920’s music evolving into blues..it was amazing. I recommend and appreciate people like our guide who obviously value our city’s richest history. This was more than a gangsta historical tour, you learn a lot more about origins and impacts. I left being a little extra proud of our city. Thank you! 🎩💐

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.