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
4.8
(113 Ratings)
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833maxo
Nov 21, 2025
Outstanding! - Outstanding! Winnie (aka Carmen) transported us back into 1920s bootlegging Chicago and stayed in character throughout the tour. Taking us through the different gangs, characters and parts of the city. Very entertaining, informative and humorous. We highly recommend this tour!
Review provided by Tripadvisor
Nancyee149pi
Nov 15, 2025
Fun and informative - Exceeded expectations! Winnie was wonderful as a guide and made it fun right from the beginning. Keeping the commentary within the vernacular of the times was impressive!
Review provided by Tripadvisor
Lilyf24601
Oct 28, 2025
Be transported back in time - A fantastic tour with great information with Chicago slang. We are one mafia buff and one newbie, and the content was appropriate for both. I was very happy to win the prize in the raffle! Winnie was our guide and she was great. For our short time in Chicago, this was perfect.
Review provided by Tripadvisor
Tim_m
Oct 27, 2025
Tour guide was great.... - Tour guide was great. Very interesting tour. Good review of the city mob areas. A stop midway through the tour would be nice.
Review provided by Viator
Ann_s
Oct 27, 2025
What an adventure! - Marie was great. We enjoyed the tour very much. She was informative and funny. Very impressive. We were visiting from Arizona and when friends gave me the list of tours this one caught my attention as my parents were born in that era and my dad was an Indiana State trooper in the 40’s. I will recommend this adventure to anyone I know is visiting Chicago.
Review provided by Viator
Eispick
Oct 26, 2025
Fun and a guide with Passion - We had Fun and a great experience south and north of the city. Our local guide was passionated and knowledgeable. great tour
Review provided by Tripadvisor
3thek
Oct 16, 2025
Great!! She was a lot of fun and good stories - Toni was great and the driver was very safe and kind . Beautiful day very kind, great sense of humor and very kind ….,,,,,,
Review provided by Tripadvisor
Karen_h
Oct 11, 2025
Entertaining Tour - The host was very knowledgeable and entertaining. The tour was comfortable and enabled us to learn about that era.
Review provided by Viator
Katie_m
Oct 5, 2025
Very interesting and fun tour - Such a fun and interesting tour. Perfect for a hot/cold day as we were in a temperate controlled bus the whole time. “Marie Jenko” was a perfect T tour guide!
Review provided by Viator
Clark_r
Sep 22, 2025
A Must event - This tour was absolutely fun and informative beyond expectations. Marie was so entertaining and hilarious. You will find out more about Chicago than just gangsters.
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).