Top Chicago Crime Tours

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

Chicago Architecture and True Crime: Halloween Edition

1 hour 30 minutes to 1 hour 45 minutesFree 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.

Chicago Gangsters and Ghosts Walking Tour

Chicago Crime, Mobsters & Ghosts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

1 hour 30 minutesFree Cancellation

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

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.

Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

Chicago Murder Mystery Tour

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

Original Chicago Prohibition Bus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer House, where Al Capone once mingled, and pass the Congress Hotel, rumored to be haunted by ghostly figures. Drive through Grant Park to learn about H.H. Holmes and the chilling Iroquois Theatre Fire. At each stop, delve into gripping tales of rivalries, secret doors, and tragic events that shaped Chicago's past. This tour is perfect for history buffs and those intrigued by the darker side of the city. - Explore key sites linked to Al Capone and Chicago's gangland history - Discover chilling tales of hauntings, Death Alley, and the tragic Iroquois Theatre Fire - Enjoy stops at iconic locations like the Holy Name Cathedral and Grant Park - Engage in a unique paranormal photo opportunity by the Chicago River

Chicago Gangsters and Ghosts Minibus Tour

Chicago Haunted Interior Architecture Ghost Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate. On this tour, you’ll hear how the culture in turn-of-the-century Chicago helped bring about the 18th Amendment through stories of notorious vice districts along the Chicago River and the South Loop. We'll talk about the rise of Al Capone during the infamous “Beer Wars,” culminating in the St. Valentine’s Day Massacre. Along the way, we’ll talk about how the city played a role in the popular and artistic growth of jazz, and how Chicago during the Roaring Twenties has been depicted on screen, in blockbusters such as "The Untouchables" and "Chicago." Please be advised that this tour contains stories of murder and sex work. Although children are welcome on this tour, parents should use their discretion in determining whether it is suitable for those under 15.

Prohibition Chicago: Myth vs. Reality Walking Tour

Chicago Gangster History Walking Tour of River North

Price varies by group size

3 hours 30 minutesFree Cancellation

Walking Prohibition 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.

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

1 hourFree Cancellation

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What are people saying about Chicago

Chicago Architecture and True Crime: Halloween Edition

Jennifer_F, Sep 2026

David was a fantastic...

David was a fantastic storyteller and guide! He really knows his history and provided detailed information and stories that brought some of these beautiful buildings to life. He added some great humor and wit which made the your even more entertaining. His answers to questions werent just thorough but also provided additional stories. His passion made the tour a great one. I highly recommend taking time to do this tour, its a great companion tour after doing a boat tour where you get inside the buildings the boat tour goes past plus the darker stories that go with the architecture.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Ambre_P, Jul 2026

Great guide and a cool way to see the city

Andre was one of the best walking tour guides that we’ve ever had and we’ve taken many tours across the states and Europe. His love for history, Chicago, and crime bosses was evident. Boring is not a word that would ever describe him! My 11 year old son loved talking to him and seriously wants to be BFFs with him! I highly recommend this tour!

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 Crime, Mobsters & Ghosts 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.