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Untouchable Tours
Photograph: Courtesy Untouchable Tours

The best crime tours of Chicago

Explore the seedy underbelly of Chicago on these fascinating crime tours

Annalise Mantz
Erin Yarnall
Written by
Annalise Mantz
&
Erin Yarnall
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Chicago is well known for its towering architecture, amazing restaurants and beautiful beaches, but the city also has a notorious history of Prohibition-era organized crime and violence. Some of Chicago’s most beautiful streets have dark pasts, and you can explore the oftentimes grisly history on a Chicago crime tour. Guides unearth the city’s darkest stories, and some of them even make stops at local restaurants and bars to help set the scene. While the tours may be a bit eerie, some can be experienced on your own schedule, whether in-person or virtually. Experience Chicago history hidden in plain sight on the best Chicago crime tours.

RECOMMENDED: Check out the full guide to the best Chicago tours

Crime tours of Chicago

Chicago Crime and Mob Tour
Photograph: Andrew Nawrocki

Chicago Crime and Mob Tour

Follow in the footsteps of infamous gangsters like charming bank robber John Dillinger and Polish mobster Hymie Weiss on this bus tour. You’ll hear stories about the who’s who of Chicago organized crime, drive by a few murder locations and spot the historic courthouse where many criminals were thrown in the clink.

Untouchable Tours' Original Gangster Tour
Photograph: Courtesy Untouchable Tours

Untouchable Tours' Original Gangster Tour

For more than 30 years, Untouchable Tours has been driving tourists back and forth across the city—not to see sights like the museum campus or the Willis Tower, but instead to see the staircase in front of a church that’s covering up bullet holes and the empty lot where the St. Valentine’s Day Massacre took place. The two-hour tour features guides that take on the persona (and snappy garb) of ’20s gangsters. Guides tell the tales of prohibition-era Chicago and what it was like when gangsters like Al Capone, Bugs Moran and Hymie Weiss walked the streets.

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Gangsters and Ghosts Tour in Chicago
Photograph: Andrew Nawrocki

Gangsters and Ghosts Tour in Chicago

The towering skyscrapers and shining facade of Cloud Gate might make the Loop seem glitzy and glamorous, but it was once a hotspot for vice. In the ’20s and ’30s, this nabe was the epicenter of bootlegging and gangbanging in Chicago. Take a walking tour through the area to spy speakeasies, secret underground tunnels and maybe even a ghost or two.

Vice, Crime and Gangsters in Chicago: A Self-Guided Audio Tour
Photograph: Dr. Richard Junger

Vice, Crime and Gangsters in Chicago: A Self-Guided Audio Tour

There are endless upsides to taking tours of a city, but there are downsides as well—most notably, not being able to explore at your own pace. That’s not the case with the self-guided Vice, Crime and Gangsters in Chicago tour. The 31-stop audio tour starts at the Dusable Bridge and winds its way through notorious locations in the Loop and River North, including Chicago’s first vice district and the site of the Lager Beer Riot. It’s narrated by professor, urban historian and former journalist Richard Junger, who has written books on Chicago history.

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Chicago Night Crimes Tour
Photograph: Courtesy Viator

Chicago Night Crimes Tour

See the sites of grisly killings under the dark of night on this evening bus tour. You’ll visit the Biograph Theater where Dillinger met his end, the site of the St. Valentine’s Day Massacre and other infamous locations. The bus even stops at a few historic watering holes like Harry Caray's so you can raise a glass to the city's dearly departed criminals.

Lincoln Park Hauntings Ghost Investigation Tour
Photograph: Mike Huberty

Lincoln Park Hauntings Ghost Investigation Tour

On the surface ghost tours and crime tours are two separate entities. But how does one become a ghost? Death. And how does someone’s death become notable enough to end up on a tour? It’s got to have some sort of criminal element, right? This ghost investigation tour is led by a paranormal investigator who takes guests through some of the eeriest locales in Lincoln Park, including the site of the St. Valentine’s Day Massacre. It also offers an opportunity to use paranormal activity-detecting equipment to help you determine if you just saw a ghost or a very exhausted DePaul student.

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Private Al Capone Gangster Tour
Photograph: Courtesy Viator

Private Al Capone Gangster Tour

Al Capone’s trademark look—thick eyebrows, jaunty hat, heavy overcoat and a cigar hanging from his lips—became the basis of the stereotype of the mafia man. Capone got his start in New York as a member of the Five Points Gang before founding the Chicago Outfit and wreaking havoc on the Midwestern city. Follow in his nefarious footsteps on this tour around the city in a private town car—in true mafioso style.

Private Chicago Mafia and Blues Evening Tour
Photograph: Shutterstock

Private Chicago Mafia and Blues Evening Tour

After a long night of making dirty deals and plotting the downfall of their enemies, Chicago mobsters used to unwind with some booze and live music at a mafia-friendly bar. You’ll do the same on this private guided tour that hits several historic landmarks before stopping for a drink at a bar formerly owned by Capone himself.

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Mysterious Chicago Virtual Tours
Photograph: Adam Selzer

Mysterious Chicago Virtual Tours

During the pandemic, Mysterious Chicago had to adapt. No longer able to offer in-person tours of some of Chicago’s most notorious locales, the tour company pivoted to offering virtual live tours on Facebook. Tour guide Adam Selzer has been hosting donation-based virtual tours every single day that focus on a wide range of topics, including Grave Robbing 101 and Unsolved Mysteries from Chicago History. Selzer, the author of “Mysterious Chicago” also offers private tours and his in-person tours will resume in the spring.

Family Secrets Tour
Photograph: Courtesy Frank Calabrese

Family Secrets Tour

Frank Calabrese Jr. was born into the mob: His father Frank Calabrese Sr., a high-profile Chicago Outfit mobster and murderer, brought him into the family business at age 19. Unlike his father, however, Frank Jr. got out of organized crime by cooperating with the FBI—a process that landed his father in max for life. These days, Frank Jr. leads fascinating tours of his old stomping grounds to give visitors an inside look at Chicago’s criminal underworld.

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Devil and the White City Tour
Photograph: Courtesy Weird Chicago Tours

Devil and the White City Tour

In addition to a thriving mob community, Chicago was also home to one of the country’s first known serial killers: H. H. Holmes. The insurance scammer and con man lured hundreds of people to the three-story hotel that would later be known as the Murder Castle: a labyrinth of trap doors, peepholes, dead-end stairways, gas chambers and crematorium that he used to murder his victims and dispose of their remains. To this day, authorities still don’t know how many people he might have killed. Learn the disturbing facts of the case on a Weird Chicago walking tour.

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