Chicago Prohibition Tour: Gangsters and Landmarks

Explore Chicago’s Prohibition Era with actor-led gangster tours. Visit infamous sites and hear thrilling tales of Capone and Dillinger. Book now!

Duration: 1 hour, 45 minutes
Cancellation: 24 hours
Highlights
  • Biograph Theatre - Visit the location where John Dillinger met his end.
  • Holy Name Cathedral - Explore the renowned cathedral where Dean O’Banion once sang in the choir as a boy. Later in life, his North Side Gang operated a flower shop called Schofield’s across the street, which provided flowers for mob funerals. In 1924, O’Banion was murdered in his flower shop.
What's Included
  • Raffles and Prizes
Additional Information

Our tour guides provide a precise portrayal of events in Chicago during the Prohibition Era of the 1920s and 1930s. You’ll get to know about the daring feats of Capone, Moran, Dillinger, and their cohorts! Highlights include the St. Valentine’s Day Massacre, the Biograph Theater, and Holy Name Cathedral. Not only is the tour informative, but it’s also…

Location
600 N Clark St
North Clark Street
Meet the Gangster Guides at 600 N Clark Street (on CLARK between Ohio and Ontario) outside the McDonald's.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(44 Ratings)
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Kristin_r
Jan 19, 2025
Untouchable - The tour guide’s commentary was very informative, engaging, and comedic. She was great about taking us back in time! Would have been more meaningful to get out at some of the stops for just a few moments, but still super enjoyable and worthwhile. The raffle was a fun idea. Glad we did it and recommended it to several others.
Review provided by Viator
Explorer50953042096
Jan 11, 2025
Fun tour! - Fun tour! Worth the money for an informative trip around town. Learned some new things about Chicago gangsters. Kate sent me!
Review provided by Tripadvisor
Jamesjr
Dec 30, 2024
Excellent tour! - Very informative and fun tour! We had a great time and learned about the Chicago gangster history. The tour guide was excellent!
Review provided by Viator
Jsf6031mc
Dec 22, 2024
You should take this entertaining tour! - Lots of fun! Westside Wendy did a great job of sharing Mobster history while entertaining us. Awesome way to see Chicago in December.
Review provided by Tripadvisor
Patricia_w
Dec 6, 2024
Fun and informative! - This tour was great! Our guide, Marie was smart and very funny. We learned a lot about Chicago and it's fascinating gangster history while having a lot of laughs along the way!
Review provided by Viator
939kjirstenf
Nov 30, 2024
A ride through a bloody drunk history - Marie was a great tour guide! Wish we could have gotten out at certain destinations of the tour. But it was cool to see a range of Chicago.
Review provided by Tripadvisor
Dodie_r
Nov 9, 2024
Great tour - Hands down the best Mob tour!! Got to see ALOT of historical places plus the history that our guide shared was amazing!! Winnie was a great guide with lots of enthusiasm
Review provided by Viator
Amidavisatx
Nov 3, 2024
Great tour, Jonny Rocco is the best! - Jonny Rocco was fun, informative, knowledgeable, and friendly. Great tour to learn about the underground MOB scene and see the city. Highly recommend!
Review provided by Tripadvisor
Albert_k
Oct 21, 2024
Get down & duck as the bullets fly by - Tour was well worth the money. Our tour guide Rocco was so knowlegeable & funny. I highly recommend this tour to hear about Chicago's past.
Review provided by Viator
N19bhchrisg
Dec 14, 2024
Disappointing tour. - Tour guide Tony was late showing up, she was disorganized and disheveled. We were very disappointed in her story telling, she knew the headlines but not the details. She jumped from one story to another, trying to follow along was difficult. I would not recommend this tour and I will not book another one from this company.
Review provided by Tripadvisor
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