The 15 Best Chicago Gangster & Prohibition Tours

1.Gangsters and Ghosts Walking Tour

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

Explore Chicago’s Loop through true gangster tales, Al Capone sites, haunted hotels, and ghost stories on a lively two-hour walking tour.

“It was a very cold, windy Chicago night but the tour guide braved it out so we did too--and so glad we did! It was interesting listening to all of the stories about Chicago while wallking around the streets at night. We really enjoyed the tour but will never swim in the water in and around Chicago! Lol”

Check availability →Read our full review

2.Chicago Crime and Mob Bus Tour

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

Explore Chicago’s mob past by coach, with Al Capone sites, the Biograph Theatre, St. Valentine’s Day Massacre site, and Nitti’s vault.

“Great tour guide! Windows of bus were fogged, couldn’t see anything but stories were great! Good length but they need to fix the windows in winter with fogging!”

Check availability →Read our full review

3.Gangsters and Ghosts Guided Walking Tour

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

Explore Chicago’s gangster past and ghost lore on a historian-led South Loop walk through Death Alley, the Riverwalk, and haunted hotels.

“Sophia was very informative and very friendly! Was a last minute book and we enjoyed it, especially the Palmer brownie!”

Check availability →Read our full review

4.Mob and Crime Bus Tour

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

Explore Chicago mob history by bus, from the St. Valentine’s Day Massacre site to Dillinger’s final steps, with live stories and crime artifacts.

“Jay was a great tour guide! Really informative! Really enjoyed the tour!! The bus was quite loud and squeaky and it was hard to hear even with her speaker on full volume!”

Check availability →Read our full review

5.Chicago Gangster and Food Walking Tour

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

Taste steak, deep dish, and a Chicago Dawg while exploring River North gangsters, secret tunnels, Gold Coast streets, and church bullet holes.

“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!”

Check availability →Read our full review

6.Gangsters and Food Tasting Walking Tour

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

Taste Chicago pizza, steak, and a hot dog while exploring Capone-era hideouts, mob landmarks, and River North with a local guide.

“Baylor was very knowledgeable and easy to spend time with during the tour. We enjoyed her company! The food was fantastic and everything was very organized. Highly recommend!”

Check availability →Read our full review

7.Prohibition Speakeasies Bus Tour or Walking Tour

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

Explore Chicago’s Prohibition past at three or four speakeasies on a lively walking or neighborhood bus tour with drinks extra.

“Amazing historical and highly entertaining tour of Chicagos dark past! Our tour guide Jonathan was absolutely spectacular and his commentary flowed effortlessly as well did the booze at each of the fine establishments we visited throughout the city. By far the best tour and guide in Chicago. We plan on taking this again and will bring family and friends anytime they visit the city.”

Check availability →Read our full review

8.Chicago’s Original Gangster Tour by Bus

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

Ride through Chicago’s mob past on a lively 1-hour-45-minute minibus tour with costumed guides, historic sites, and sharp city stories.

“The tour guide was knowledgeable, interesting to listen too and made the tour so much fun. You don’t get off the bus and at first I wasn’t sure I’d like that but it was good, you didn’t really need to in order to enjoy.”

Check availability →Read our full review

9.Prohibition-Era Culture & Architectural Treasures

★★★★★★★★★★4.8 · 93 reviews · from $49

Walk Chicago’s Prohibition-era streets, admire landmark architecture, taste local popcorn, and finish at Millennium Park for $49.

“I had the absolute pleasure of touring Chicago with Dash, and it was nothing short of phenomenal. Dash didn’t just recite facts—he brought the city’s architectural heritage and hidden treasures to life with a depth of knowledge and a genuine passion that made every moment memorable. His storytelling was rich, engaging, and personal, making me feel like I was experiencing Chicago through the eyes of someone who truly loves it. This wasn’t just a tour; it was an immersive journey through history, art, and culture. If you want to see the real beauty and soul of Chicago, Dash is the guide you need!Read more”

Check availability →Read our full review

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

★★★★★★★★★★5.0 · 87 reviews · from $49

Walk Chicago’s Loop from the Chicago Theatre to the Bean, with Prohibition tales, landmark architecture, Pedway history, skyline views, and local treats.

“The walk tour is something not to be missed for three reasons, especially when you’re on a short trip. Our guide, “tall Dave”, knows a lot about the history of the places we visited, shows interesting photos, and makes sure everyone is well accommodated. The sites have very fascinating architecture, some of them are hidden gems that do not usually appear in top places to visit when you Google. Finally, the group is pretty small, hence, it’s easier to interact with the guide, ask questions, and have fun with fellow tourists. So if you’re planning to visit Chicago, this tour should be in your checklist.”

Check availability →Read our full review

11.Historic Gangsters & Twilight Tales Night Cruise

★★★★★★★★★★4.1 · 63 reviews · from $45

Cruise Chicago’s river at twilight while hearing eerie tales of mobsters, disasters, H. H. Holmes, and the city’s glowing skyline.

Check availability →Read our full review

12.Chicago Gangsters and Movies Tour

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

Explore Chicago mob stories and movie locations on a 90-minute walking tour with guide Andre, from the Riverwalk to the Cultural Center.

“Very interesting. Explored parts of Chicago we would never have found. Our tour guide Andre was extremely knowledgable and enthusiastic, making our tour a brilliant experience. Highly recommend this tour to everyone. 5* from us 👌”

Check availability →Read our full review

13.Chicago Gangsters and Ghosts Luxury Minibus Tour

★★★★★★★★★★5.0 · 33 reviews · from $49

Explore Chicago gangster lore, ghost stories, Frank Nitti’s vault, Death Alley, and Loop landmarks from a comfortable tour bus for $49.

“The tour guide was very informative. Very sweet. It was a fun and amazing experience. Glad we had this opportunity. Everything was timed perfectly.”

Check availability →Read our full review

14.Vito’s Vault Chicago finest dinner theatre speakeasy

★★★★★★★★★★5.0 · 14 reviews · 3 hours (approx.) · from $88

Step into 1929 at Vito’s Vault for a Chicago speakeasy dinner, steak or salmon, homemade hooch, and a 90-minute comedy revue.

“It’s a Roaring Twenties experience with dancing and singing. There are also lots of jokes and gags with customer participation.”

Check availability →Read our full review

15.3-Hour Private Speakeasy Cocktail VIP Tour

★★★★★★★★★★5.0 · 7 reviews · 3 hours

Explore Chicago’s Prohibition-era speakeasies by secret entrances, with cocktails, gangster tales, private transport, and a personal guide.

“Alan, our host, was knowledgeable, kind and funny. He took us to great spots and made everything so fun. It was a huge hit with my group.”

Check availability →Read our full review