15 Best Gangster & Crime Tours In Chicago

Chicago, Gangster & Crime Tours, Ghost & Haunted Tours, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Ghosts Walking Tour

/ June 4, 2026

1.Chicago: Gangsters and Ghosts Walking Tour

A historian-led Chicago Loop walk mixing Prohibition-era mob stories and reported ghost sites, with optional minibus upgrade for $52.

Chicago Crime and Mob Bus Tour

/ June 4, 2026

2.Chicago Crime and Mob Bus Tour

A $49 coach tour through Chicago’s mob history with photo stops, mini museum, and story-first guides. 90–120 minutes of crime scenes.

★ 4.5

“Lots of interesting facts. the tour guide was great! I would do this tour again! Got to stop at Harry Carey restaurant and see an underground Chicago tunnel and a vault got to see the place where John Dillinger met his demise. Very interesting tour.”

3,186 reviews1 hour 30 minutes to 2 hours (approx.)From $49.00by Chicago Crime Tours and Experiences LLC

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Chicago, Gangster & Crime Tours, Ghost & Haunted Tours, Guided, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Ghosts Guided Walking Tour

/ June 4, 2026

3.Chicago: Gangsters and Ghosts Guided Walking Tour

Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.

★ 4.7

“Great experience with Alan, he was so good at explaining everything and had loads of info and knowledge to share”

1,697 reviews2 hoursFrom $36by Empire Tours & Productions (Chicago Gangsters and Ghosts Tours)

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Chicago, Gangster & Crime Tours, Tour Reviews, Tours

Chicago: Mob and Crime Bus Tour

/ June 4, 2026

4.Chicago: Mob and Crime Bus Tour

A 90-minute Chicago mob-and-crime bus tour with photo stops, a mini mob museum, and a guided walk tied to Dillinger.

★ 4.4

“Our rep was massively impressive and fun, she has so much knowledge and experience”

746 reviewsFrom $49by Chicago Crime Tours and Experiences LLC

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Chicago, Evening Experiences, Gangster & Crime Tours, Tour Reviews, Tours

Chicago Night Crimes Tour by Bus

/ June 4, 2026

5.Chicago Night Crimes Tour by Bus

Ride Chicago by night on a bus gangster tour with live narration, photo stops, and stops at Biograph Theatre, Nitti’s Vault, and the Water Tower.

★ 5.0

“Great time , guide was amazing . See things that you would never find on your own. The pizza at the end was a nice touch”

478 reviews2 hours to 2 hours 30 minutes (approx.)From $55.00by Chicago Crime Tours and Experiences LLC

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Chicago, Food, Food & Drink, Gangster & Crime Tours, Tour Reviews, Tours, Walking Tours

Chicago Gangster and Food Walking Tour

/ June 4, 2026

6.Chicago Gangster and Food Walking Tour

Prohibition-era gangster stories meet Chicago food in 2 hours. Small-group walk with Harry Caray steak, deep-dish pizza, and dawgs.

★ 5.0

“Taka is a great story teller! We throughly enjoyed our time exploring the city with a fun gangster twist and food. Loved the Chicago Hot Dog the best!”

471 reviewsFrom $79by Chicago Tours

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Chicago, Gangster & Crime Tours, Ghost & Haunted Tours, Tour Reviews, Tours, Walking Tours

Chicago Mobs and Haunts Walking Tour

/ June 4, 2026

7.Chicago Mobs and Haunts Walking Tour

Chicago Mobs and Haunts walking tour mixes Capone hangouts, haunted hotels, and ghost stories in the Loop for $34 in under 2 hours.

★ 4.5

“Ben was exceptional, energetic and full of knowledge. I loved listening to him talk. Had a wonderful time.”

383 reviews1 hour 30 minutes to 2 hours (approx.)From $34.00by ExperienceFirst

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Chicago, Gangster & Crime Tours, Tour Reviews, Tours

Chicago Architecture and True Crime Tour

/ June 4, 2026

8.Chicago Architecture and True Crime Tour

A $35 Loop walking tour that pairs Chicago architecture stops with true-crime stories, lots of indoor time, and great photo moments.

★ 5.0

“Knowledgeable and friendly tour guide. Learned a lot about the city and despite being cold we thoroughly enjoyed it. Would highly recommend!”

326 reviews1 hour 30 minutes to 1 hour 45 minutes (approx.)From $35.00by Local Chicago Tours

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Chicago, Food, Food & Culinary Tours, Food & Drink, Gangster & Crime Tours, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Food Tasting Walking Tour

/ June 4, 2026

9.Chicago: Gangsters and Food Tasting Walking Tour

Chicago gangster food walk with Capone-style tunnel access, River North stories, and tastings of deep dish pizza, steak, and a Chicago hot dog.

★ 4.6

“We absolutely loved our tour with Alan! The experience was amazing from start to finish, completely exceeding our expectations. Alan was friendly, fun, and you can really tell he loves what he does. He showed us incredible spots around the city, always patient and attentive to the group. I highly recommend his tour—it’s definitely a…”

228 reviews2 hoursFrom $81by Empire Tours & Productions (Chicago Gangsters and Ghosts Tours)

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Chicago, Gangster & Crime Tours, Tour Reviews, Tours

Chicago’s Original Gangster Tour by Bus

/ June 4, 2026

10.Chicago’s Original Gangster Tour by Bus

Chicago’s Original Gangster Tour by bus is a small-group, 1h45 ride through mob hotspots with costumed storytelling and city comforts.

★ 5.0

“Really enjoyable tour. Information & stories were told in character and was so well done. Well worth doing the tour”

116 reviews1 hour 45 minutes (approx.)From $48.00by Untouchable Tour - Chicago's Original Gangster Tour

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Chicago, Evening Experiences, Gangster & Crime Tours, Tour Reviews, Tours

Chicago Crimes Night Tour

/ June 4, 2026

11.Chicago Crimes Night Tour

Chicago Crimes Night Tour is a 2-hour guided coach ride to the St. Valentine’s Day Massacre, Dillinger’s last steps, and mob-era stops.

★ 4.5

“Great information and knowledge and loved being able to view the sites were amazing.”

89 reviews2 hoursFrom $55by Chicago Crime Tours and Experiences LLC

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Chicago, Cruises & Boat Tours, Evening Experiences, Gangster & Crime Tours, Ghost & Haunted Tours, Historical Tours, Tour Reviews

Chicago: Historic Gangsters & Ghosts Night Cruise

/ June 7, 2026

12.Chicago: Historic Gangsters & Ghosts Night Cruise

A 90-minute Chicago River night cruise with skyline views and spooky stories about disasters, the Chicago Fire, and H. H. Holmes.

★ 3.9

“So much fun and so much history fed onto us in forms of tales and stories. Loved it all!”

45 reviewsFrom $45by First Lady

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Chicago, Gangster & Crime Tours, Tour Reviews, Tours

Chicago Gangsters and Movies Tour

/ June 10, 2026

13.Chicago Gangsters and Movies Tour

A 90-minute Chicago walking tour mixing gangland stories and famous movie filming spots, with included souvenir photos for $35.

★ 5.0

“We had a great afternoon! He kept kids, parents and grandparents engaged alike! He included context and character to provide great meaning and engagement. A top highlight were his many callouts on Al Cappone!”

38 reviews1 hour 30 minutes (approx.)From $35.00by Magnifico Tours

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Chicago Gangsters and Ghosts Luxury Minibus Tour

/ June 10, 2026

14.Chicago Gangsters and Ghosts Luxury Minibus Tour

A 2-hour minibus tour of the Chicago Loop’s Prohibition-era gangs and ghost stories, with big photo moments and key landmark stops.

★ 5.0

“We had a good time and learned some interesting history about Chicago. Our tour guide was named Alan. He was personable and fun. I would recommend this tour.”

33 reviewsFrom $49by Chicago Tours

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