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
(97 Ratings)
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Whatablastthatday
Aug 25, 2025
Great Gangster Tour! - What a fun tour! Winnie Westside was great-so personable and fun -her stories were great! Would definitely recommend!!
Review provided by Tripadvisor
Lisacl8819qb
Aug 23, 2025
Excellent Tour - Excellent tour! Small and cozy and Marie was an incredible guide. Highly recommend! Great history lesson and very entertaining.
Review provided by Tripadvisor
Leigham541
Aug 23, 2025
Good time - Great way to learn and hear about Chicago. Kate was a great guide. $$ well spent. Tour goes around all sides of the city on a temp controlled bus and a lot of cool sites are visited.
Review provided by Tripadvisor
Sara
Aug 22, 2025
Fantastic experience about old Chicago - Winnie Westside was our guide- we loved this tour! Would highly recommend and would do it again. Tour started promptly and the bus was nicely air conditioned. The stories and history were on point. We got to see many different neighborhoods. Winnie was so funny and kept us entertained the whole time. We learned a lot and enjoyed this very much.
Review provided by Tripadvisor
Helen_w
Aug 15, 2025
Great tour - Really enjoyable tour. Information & stories were told in character and was so well done. Well worth doing the tour
Review provided by Viator
Steve_b
Aug 8, 2025
Great historical trip... - Great historical trip around city with added kick of gangster. Crew is great and very educational but fun
Review provided by Viator
Mariadolores_l
Aug 8, 2025
Comfortable fun tour - The tour guide was knowledgeable and funny. I thought we would get out of the vehicle to explore some sites but as it turns out through no fault of the company, many of the sites are not there anymore or they are privately owned businesses that you couldn't go into anyway. Still the tour was very interesting, and again the tour guide was fun
Review provided by Viator
Ann_l
Jul 27, 2025
Iowans for gangsters - Bus tour with gangster history delivered with fact and humor. Most of the sites are no longer present. Tour of many city neighborhoods to cover the North, South, West gangs.
Review provided by Viator
Paul_p
Jul 27, 2025
Great tour - Well informed tour around Chicago on gangsters! Talk guide great entertainer along with the gangsters raffle
Review provided by Viator
Marcella_k
Aug 9, 2025
It was a limousine bus;... - It was a limousine bus; therefore we could not really “ see”. An open trolley would be perfect. Thank you
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).