The 15 Best Chicago Gangster 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, hearing stories of Al Capone, bootleggers, and reported hauntings at places such as the Palmer House and Congress Plaza Hotel. The tour lasts about two hours, with frequent stops and a refreshment and restroom break. A bus upgrade is available, with one stop at Harry Caray’s Italian Steakhouse.

“This was a very interesting and also funny tour! Our guide Tanner was amazing!!! We had a very good time”

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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

The Chicago Crime and Mob Bus Tour takes you from Pearson Street through River North, the Loop, Lincoln Park, and other neighborhoods tied to Chicago crime. An English-speaking guide shares stories of Al Capone, Bugs Moran, John Dillinger, and more, with photo stops at sites such as the Biograph Theatre and a visit to Harry Caray’s mini mob museum.

“Jamie was a great guide, very comedic, informed, prompt, and a great photographer too! It was nice being able to stop and learn about some of the history of Chicago. I highly recommend!”

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3.Gangsters and Ghosts Guided Walking Tour

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

Join an English-speaking historian guide for a 1.5-mile walk through Chicago’s South Loop, where Prohibition-era gangsters and ghost legends meet at landmarks including the Riverwalk, Palmer House and Congress Hotel. The $36 tour includes entry inside the Palmer House and Congress Hotel, plus a midway break at a former gangster hangout.

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

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4.Mob and Crime Bus Tour

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

This 90-minute Chicago crime tour pairs an English-speaking guide with a climate-controlled coach, photo stops and short walks. Hear stories about Al Capone, John Dillinger and other criminals, then see a mini mob museum featuring Frank Nitti’s safe and address book. Guides such as Jay and Katie have led engaging, story-rich tours.

“Myself, husband, and 11 year old had a great experience. Tour guide was informative and we saw sights around Chicago we wouldn't have. Just the right amount of on and off.”

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5.Chicago Gangster and Food Walking Tour

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

Walk River North and the Gold Coast with a guide, hearing Chicago gangster stories as you sample steak, deep-dish pizza, and a Chicago hot dog. You’ll see the tunnel at Harry Caray’s and stop by Holy Name Cathedral, where bullet holes from a 1920s shooting are still visible. The tour lasts about two hours and caps groups at 15.

“Avery was awesome, he went above and beyond Great tour, wonderful tour guide We all had a great time Loved it Sue Hockman”

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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

Walk through Chicago’s Loop with a local guide, pairing landmark architecture with true-crime stories about the city’s darker past. The route begins at the Palmer House Hilton, includes time inside several historic buildings, and ends at Chase Tower. Guides featured on recent tours include Joseph, David, Kris, Roan, and Johnathan; the guide for your date may differ.

“David was such a fantastic, knowledgeable host! We learned a lot about some really cool architecture in the city, and some really interesting true crime stories! Would definitely recommend this tour to others.”

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7.Gangsters and Food Tasting Walking Tour

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

Walk about a mile through River North with a local English-speaking guide, sampling Chicago steak, pizza, and a hot dog while hearing stories of Capone-era gangsters. Stops include an old tunnel in Harry Caray’s restaurant, a former gangster hideout, and sites tied to notorious Chicago history. Guides such as Alan, Talia, and Baylor have led the tour.

“Our guide Baylor was great! She was well informed and friendly. The food was great. Our favorite part was going down to see hidden tunnel in Harry Caray restaurant. Thank you”

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8.Chicago’s Original Gangster Tour by Bus

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

This 1-hour-45-minute Chicago minibus tour visits about 10 sites tied to the city’s gangsters and Prohibition-era past. Expect a costumed guide, lively stories, and views across North, South, and West Side neighborhoods. Guides have included Marie, Winnie, and Westside Winnie. You stay aboard for most of the route, and the tour returns to 600 N Clark St.

“Great way to see Chicago. Saw gangster hot spots and learned Chicago fun facts, presented in a witty manner. I took my young adult children, who weren't exactly thrilled to go but ended up having a great time.”

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9.Historic Gangsters & Twilight Tales Night Cruise

★★★★★★★★★★4.1 · 63 reviews · from $45

Spend 90 minutes on a guided evening cruise along the Chicago River, pairing views of the Tribune Tower, Wrigley Building, Merchandise Mart, and Willis Tower with tales of the Eastland disaster, the Great Chicago Fire, H. H. Holmes, and more. The guide speaks English, and drinks are available to buy onboard.

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10.Chicago Gangsters and Movies Tour

★★★★★★★★★★5.0 · 38 reviews · 1 hour 30 minutes (approx.) · from $35

Walk through downtown Chicago with a guide who connects mob stories to scenes from The Blues Brothers, The Fugitive, The Dark Knight, and more. The 90-minute tour starts at 238 N State St and ends at the Chicago Cultural Center, with a maximum of 25 people. Souvenir photos are included; gratuity is not.

“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.”

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11.Chicago Gangsters and Ghosts Luxury Minibus Tour

★★★★★★★★★★5.0 · 33 reviews · from $49

Spend about two hours exploring Chicago’s Loop by bus with a guide and licensed driver. Hear stories tied to gangsters and ghosts, see landmarks including Holy Name Cathedral and Death Alley, and visit Frank Nitti’s vault at Harry Caray’s Italian Steakhouse. Guides have included Ty, Alan, Matthew, Kris, Avery and Karina.

“Alan was a great speaker, he gave us lots of stories and information. I would recommend this tour…..”

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12.Architecture & True Crime History

★★★★★★★★★★4.9 · 16 reviews · from $35

Meet beneath the Palmer House canopy on the Wabash side for a 90-minute walk through Chicago’s architecture and its darker history. Local guides connect Beaux Arts, Art Deco, and Modernist design with true crime stories, including tales of Gacy and Holmes. Joseph has led the tour, and the route can be adjusted if storms interrupt.

“The guide was exceptional. Really like how she told the stories”

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13.Private 3-Hour Al Capone Gangster Tour

★★★★★★★★★★4.8 · 9 reviews · 3 hours

Ride with a historian guide and chauffeur to Chicago mob-era sites, including the St. Valentine’s Day Massacre location, a theater tied to John Dillinger, and Al Capone’s booth at the Green Mill. Your private group of up to five gets hotel pickup within city limits and luxury transportation. Guides have included Conor, though your assigned guide may differ.

“I enjoyed that we had a say in what areas we wanted to focus on. We chose to do more of the Al Capone items as he was possibly a frequent visitor of a bar our family once owned in the area.”

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14.Private Al Capone Gangster Tour in Chicago

★★★★★★★★★★4.5 · 7 reviews · from $539

Visit Chicago mob sites, old speakeasies, and historic hotels with a historian guide and private vehicle. Stops include the Green Mill, the Biograph Theatre, Holy Name Cathedral, and the St. Valentine’s Day Massacre site. Hotel pickup and drop-off are included, and departure times are offered throughout the day.

“Very fun. Was already a big history buff but still learned alot from Lizzy are guide and our driver was great to.”

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15.Gangsters, Ghosts, and Haunted Hotels Segway Tour

★★★★★★★★★★4.4 · 5 reviews · 2 hours · from $77

Glide through downtown Chicago after dark on a two-hour Segway tour capped at eight people. An English-speaking guide leads you past the Congress Hotel, Death Alley, the Eastland disaster site, Fort Dearborn, and Al Capone’s haunted yacht, sharing stories of murders, fires, and unexplained events. Helmets and Segway instruction are included.

“Wow, this was pretty great. Ended up just being two of us with our guide, Tammy. She gave us a lot of great details and left us wanting more. The city was really pretty at night and she helped us navigate effortlessly. Would highly recommend. My teen son loves it.”

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