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
(66 Ratings)
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Julie_j
Jun 22, 2025
Fun times! - What a fun time. Our guide Winnie was awesome. Loved going through the old neighborhoods and learning the history of Chicago.
Review provided by Viator
Janet_t
Jun 22, 2025
Fun Historical Tour! Loved it! - What a fun historical tour. I really enjoyed it. Bus was easy to get on and off. Seats were very comfortable. Our Tour guide did a great job! She was fun!
Review provided by Viator
N4115dqjanett
Jun 21, 2025
Great Historical Fun Tour! - Great Historical Fun Tour! Really enjoyed it. Our Guide Marie made it fun! Nice way to see the city and famous landmarks.
Review provided by Tripadvisor
Monetta_n
Jun 14, 2025
That was so much fun! And... - That was so much fun! And very informative without being the least bit boring. And kudos to the bus driver for driving a bus thru Chicago!
Review provided by Viator
N2368xvdavidt
Jun 8, 2025
Gangster Tour - Fun and informative! - Marie was our tour guide. She was fabulous! Obviously, most of the original places are gone, but she painted a good picture of the circumstances that lead to the rivalries. She nicely mixed in a lot of entertainment with all the information she gave us. The bus was comfortable and the driver did a good job negotiating the traffic.
Review provided by Tripadvisor
Julie_b
Jun 7, 2025
Great guide! Colorful... - Great guide! Colorful history! Free give away at the end. Wish we could have gotten out to take pictures. Still fabulous though!
Review provided by Viator
Leeb296
Jun 7, 2025
Better than expected - Family booked this tour and no one else showed up. Hannah was our guide and she was incredible. It was 2 hours of information and stories. Because it was just us 3 we got more in depth and it was appreciated. Hannah thank you!
Review provided by Tripadvisor
Holly_b
May 30, 2025
So much fun and our guide... - So much fun and our guide was really funny! She gave us a lot of history along with the gangster stories
Review provided by Viator
Maria_u
May 24, 2025
Great experience! - The tour guide was great. She provided a lot of great information and was super entertaining. You also get to see other areas of Chicago.
Review provided by Viator
Jude_o
May 19, 2025
Fun and Facts! - It was great! Entertaining guide in costume with historical facts and sense of humor. Raffle prizes, too!
Review provided by Viator
From $48
up to 4 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).