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 great info and stops bring it all to life. Recommend highly. Our guide was full of extra tidbits and interactive.”

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

“Tanner was really nice Guide. It was a good interesting tour, with much of deap facts.”

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

“Very informative, but lots of stories not returned to once mentioned!”

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

“The tour guide was very good & told us a lot of interesting information. The pizza was a nice surprise at the end of the tour.”

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

“Give Ty a big Bonus!! He was awesome! Very informative, knew the subject, added his own twist. Chantal and Jill.”

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

“Filled with history facts about Chicago as well as mysterious lore! Great story telling and wonderful to learn some Chicago history! Lark was an awesome guide!”

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

“Johnathan was great! Very informative & had a great voice for storytelling & setting the scene. He was very personable & even had some good stories that weren’t related to Chicago’s architecture, haha. Would definitely 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

“our guide Baylor was very knowledgeable about the sites we visited and was an overall great guide. All the food was also really good, the mix of eating and walking around was really comfortable since it was not a very long distance between stops.”

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

“Excellent!!! Tour guide was fabulous. She kept you interested and she had a great sense of humor! They really did thier homework. Highly recommended.”

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

“Had a really enjoyable tour with a small group which was great, Andre was very knowledgable & filled us in with loads of interesting facts & info. We struggled to find the meeting point, it was outside The Chase building, just up from the Chicago Cinema if you need a landmark.”

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

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