Top Chicago Crime Tours in 2026

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

1 hour 30 minutesFree Cancellation

Most Chicago sightseeing tours focus on the city’s key landmarks. But on this unique excursion, you cam dig deeper than surface level, and discover some of the city’s spookiest stories. Pick between private or shared options, and set off to explore the South Loop with your guide. Along the way, see where notorious gangsters like Al Capone operated, hear about their bloody backstories, and even visit several of the state’s most haunted addresses.

Chicago Gangsters and Ghosts Walking Tour

Price varies by group size

Chicago Architecture and True Crime: Halloween Edition

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

Chicago Crime, Mobsters & Ghosts Walking Tour

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

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

Chicago Murder Mystery Tour

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

3 hours 30 minutesFree Cancellation

Walking Prohibition Tour

Downtown Chicago has a dark history hiding in plain sight. This self-guided audio tour takes you through the Loop on your own schedule, with narration on your phone at every stop. Start at the Chicago Riverwalk, where the SS Eastland rolled over at its dock in 1915. Walk into Death Alley behind the site of the Iroquois Theater fire. Hear the ghost stories of the Palmer House and the Congress Plaza Hotel, the secrets of the Rookery, and the stories beneath Willis Tower, then finish on the steps of the Art Institute. No group, no guide, and no fixed start time. Go at your own pace, stop for a drink along the way, and replay any story you like. All you need is a phone and headphones.

Chicago Loop Self Guided Ghosts Gangsters and Secrets Tour

5% savings

from

$20$19

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

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

1 hourFree Cancellation

Chicago's prettiest neighborhood hides some of its darkest history. This self-guided audio tour takes you through Lincoln Park on your own schedule, with narration on your phone at every stop. Start at the Red Lion Pub on North Lincoln Avenue, long rumored to be one of the most haunted bars in the city. Stand outside the Biograph Theater, where the FBI gunned down John Dillinger in 1934. Visit the North Clark Street site of the 1929 St. Valentine's Day Massacre. Walk into Lincoln Park, laid over what was once the city's cemetery, then finish on the Lake Michigan shore at North Avenue Beach. No group, no in-person guide, and no fixed start time. Go at your own pace, stop for a drink along the way, and replay any story you like. All you need is a phone and headphones.

Self Guided Ghosts Gangsters and Graves Tour in Chicago

5% savings

from

$20$19

Original Chicago Prohibition Bus Tour

Chicago Gangster History Walking Tour of River North

Price varies by group size

We are the original, top-rated Gangsters and Ghosts tour! As a private tour, hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your private 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 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

Price varies by group size

Must-Dos in Chicago

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What are people saying about Chicago

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Meghan_P, Oct 2026

Andre was friendly,...

Andre was friendly, informative and fun! We enjoyed the tour and learned a lot about not only “ haunted” Chicago but also some of the general history. It goes by quickly and was not tiring at all. We had great weather so it was very comfortable. He had dinner recommendations and very willing to answer any question. I’d recommend!

Chicago Gangsters and Ghosts Walking Tour

Mike_M, Oct 2026

Great tour! Great guide!

We just finished a tour with Braeden. He did an amazing job. Our group size was large, because someone called in sick. That didn't bother Braeden and it didn't impact the tour. He did an excellent job of weaving ghost stories with the gangster stories. This was a great way to meet the interests of everyone on the tour. The 3 of us loved the experience and highly recommend it.

Chicago's Original Gangster Tour by Bus

Janet_W, Jul 2026

Get a great tour about the gangster era!

It was fun and the person giving the tour was in character with his clothing and accent. He really had the gangster era down pat and was funny too. We toured neighborhoods of where gangsters had hung out and were shown areas where Dillinger got shot and the St. Valentine's Day massacre, for example. My main reason for taking a trip to Chicago was to go on the Gangster Tour and I was not disappointed.

Chicago Crime, Mobsters & Ghosts Walking Tour

Lynn_H, Apr 2026

Lark's Knowledgeable and Entertaining Tour

Lark was a fantastic tour guide- knowledgeable, enthusiastic, and genuinely engaging. Our group was small, which made the experience feel personal and easy to connect with. We were able to ask plenty of questions, and Lark handled each one with ease and insight. His depth of knowledge about Chicago's history was especially impressive. He shared fascinating stories and facts that we never would have discovered on our own. The places we visited were rich with historical significance, and his storytelling made each stop come alive. We absolutely recommend Lark to anyone looking for a fun and informative tour of the city.