The 11 Best Chicago Gangster & Mob Tours

1.Gangsters and Ghosts Walking Tour

★★★★★★★★★★5.0 · 7,155 reviews · from $52Our pick

Walk about 1.5 miles through Chicago’s Loop with a historian guide such as Taka, Sophia, Tanner, or Avery. Hear true crime tales, ghost stories, and Al Capone lore while visiting the Palmer House, Riverwalk, Chicago Theatre, and Congress Plaza Hotel. A minibus upgrade is also available.

“Tour guide (Sophia) was fantastic. Not only did she have great stories to share, she shared them in a theatrical way that made them more interesting and entertaining! I was with my 18 year old son and we both enjoyed it equally!”

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2.Chicago Crime and Mob Bus Tour

★★★★★★★★★★4.5 · 3,186 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $49

Ride a climate-controlled coach through Chicago’s mob past with an entertaining local guide. You’ll see Capone and Dillinger sites, stop at the Biograph Theatre and Harry Caray’s mini museum, and hear crime stories from River North to Lincoln Park.

“We had so much fun and learned a lot! Our tour guide Mike was informative and hilarious! Would do this again!”

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3.Gangsters and Ghosts Guided Walking Tour

★★★★★★★★★★4.7 · 1,697 reviews · 2 hours · from $36

Spend two hours with an English-speaking historian guide such as Max, Baylor, Tanner, or Sophia, tracing Chicago’s gangster past and ghostly legends. Walk about 1.5 miles through the South Loop, visit Palmer House and Congress Hotel, and pause at a former gangster hangout.

“Great! Even in cold winter the walk was very enjoyable. Our guide Max was also very attentive and cheerful; We will ask for her again in our next visit soon. Hopefully not so cold!”

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4.Mob and Crime Bus Tour

★★★★★★★★★★4.4 · 859 reviews · 1h 30m · from $49

Ride an enclosed, climate-controlled bus through Chicago’s crime past, from H. H. Holmes and Leopold and Loeb to Al Capone and John Dillinger. You’ll stop for photos, visit a mini mob museum, see Frank Nitti’s safe, and hear live English commentary from guides such as Jay, Katie, and Jamie.

“Guide-Dane-was great, really enthusiastic. Loved seeing Nittis secret room.”

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5.Chicago Gangster and Food Walking Tour

★★★★★★★★★★5.0 · 471 reviews · from $79

Walk from River North to the Gold Coast with a guide such as Taka, Avery, Baylor, or Ty. See a gangster-era tunnel, bullet holes at Holy Name Cathedral, and taste steak, deep dish pizza, and a Chicago hot dog. Groups are capped at 15.

“Had a great tour with Baylor. We were the only ones on this tour so had all of her knowledge directed at us only. Interesting tour and Baylor was very chatty and friendly!”

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6.Chicago Architecture and True Crime Tour

★★★★★★★★★★5.0 · 326 reviews · 1 hour 30 minutes to 1 hour 45 minutes (approx.) · from $35Best value

Follow a local guide through Chicago’s Loop, beginning at the Palmer House Hilton and ending at Chase Tower. Expect historic interiors, bold architecture, chilling crime stories, and short outdoor walks. Guides have included Joseph, David, Kris, Roan, Johnathan, and Jonas.

“There is quite a bit of walking, partly indoors partly outdoors. Very enthusiastic and knowledgeable guide.”

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7.Gangsters and Food Tasting Walking Tour

★★★★★★★★★★4.6 · 228 reviews · 2 hours · from $81

Walk about one mile through Chicago’s River North with an English-speaking guide such as Alan, Baylor, Talia, or Peyton. Taste steak, deep dish and tavern-style pizza, and a Chicago hot dog while visiting gangster sites, a former brothel, a cathedral, and an old Capone-era tunnel.

“We had a great time on this tour and the food was so good! Our tour guide, Talia was extraordinary and very knowledgeable about mob history! Definitely worth going!!”

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8.Prohibition Speakeasies Bus Tour or Walking Tour

★★★★★★★★★★4.8 · 168 reviews · 3 - 4 hours · from $47

Choose a downtown walking tour or neighborhood bus tour through Chicago’s Prohibition past. Guide Jonathan Knotek leads you to three or four historic bars, sharing gangster stories, high-society scandals, and drink recommendations. Drinks and food cost extra, and all tours are for adults 21 and over.

“Jonathan provided a wealth of information and delivered it in a manner that kept you intrigued. All of the establishments were very welcoming. Will definitely recommend to friends and colleagues!”

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9.Chicago’s Original Gangster Tour by Bus

★★★★★★★★★★5.0 · 116 reviews · 1 hour 45 minutes (approx.) · from $48

This 1-hour-45-minute Chicago mob tour travels by climate-controlled minibus from 600 N Clark Street to about 10 gangster-era sites. Costumed guides such as Marie and Winnie mix Prohibition history, city facts, humor, and North, South, and West Side stories for a small group of up to 10.

“A very informative tour about pre and prohibition times in Chicago. Winnie our guide she presented nice, dinamic and very entertaining. She was knowledgeable and left us with very pleasant memories about this tour.”

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10.Prohibition-Era Culture & Architectural Treasures

★★★★★★★★★★4.8 · 93 reviews · from $49

Follow an English-speaking guide from the Chicago Theatre along the Riverwalk to Millennium Park. Learn how Prohibition, crime, journalism, and architecture shaped Chicago, visit the Cultural Center, see Marina Towers and the Wrigley Building, and taste Chicago-style popcorn.

“This tour was excellent! I wasn’t expecting the treats along the way so that was a very nice bonus! The tour guide Dash was lovely and flexible and you could feel his passion for his city and it was infectious. It was an amazing way to see some of the beautiful interior architecture Chicago has to offer!”

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11.Explore Chicago’s Hidden Past: Prohibition Culture & Architecture

★★★★★★★★★★5.0 · 87 reviews · from $49

Join a local English-speaking guide such as Rich, Dave, Dash, or Kevin for a 2.5-hour walk from the Chicago Theatre to Millennium Park. Expect Prohibition stories, landmark architecture, the Pedway, Chicago-style popcorn, river views, and a small group of up to 15 people.

“The buildings and their architectural history. Dave was an excellent guide! He was a very comfortable person. I felt free to ask any questions and to ask for more info.”

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