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
(57 Ratings)
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Aubryns2025
Apr 5, 2025
Al Capone Shot Glass - very entertaining Marie did a great job I loved the raffle. each character had their own persona and i loved being able to see the places where these events took place. Marie sent me
Review provided by Tripadvisor
Stephaniewu2516yp
Mar 30, 2025
Family fun for all! - Super entertaining and very informative. Our tour guide was a lady with a red hat, but I forgot her name. She stayed in character and was so fun!
Review provided by Tripadvisor
U7501uoelizabethh
Mar 29, 2025
Great for the prohibition history lover! - Enjoyed Wendy Westside! Was my daughter's second favorite experience in Chicago outside of seeing Sue in the field museum. Highly recommend! Great way to learn about Chicago history while sitting down!!
Review provided by Tripadvisor
Amy_d
Mar 16, 2025
Not only was it fun but... - Not only was it fun but also informative. We learned so much about Chicago! Our guide was awesome!!!
Review provided by Viator
Scottom6575sm
Mar 8, 2025
Mob tour is a 'blast' - Marie was excellent! Informative and funny! Learned a lot and I am from here and had read up on a few of Chicago's infamous :celebrity's gangsters. Great tour. Highly recommend!!
Review provided by Tripadvisor
40princessn
Mar 3, 2025
What make chicago so interesting - Great experience and funny stories talking about chicago. This was a very great talk about famous gangster of Chicago.
Review provided by Tripadvisor
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
Ty_h
Mar 29, 2025
The hostess was fantastic... - The hostess was fantastic telling the stories of the Chicago crime families. It was also a nice driving tour of the city.
Review provided by Viator
Cynthia_w
Apr 6, 2025
Good tour but too much time that we listened to music of the era - The information given was very interesting but there was too much lag time (time when the tour director was not talking and we listened to music). Would have liked more history
Review provided by Viator
From $45
up to 4 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).