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 guides offer a precise depiction of the events in Chicago during the 1920s and 1930s, known as the Prohibition Era. Learn about the adventures of Capone, Moran, Dillinger, and their associates! Some of the featured sites include the St. Valentine’s Day Massacre, the Biograph Theater, and Holy Name Cathedral. The tour is both educational and highly…

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
(130 Ratings)
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Cynthia_l
May 2, 2026
Marie was great!!! - It was so cool!! Marie really got into character and made it freaking amazing!! She really seemed like she was passionate about it! Made me look at Chicago in a whole other way! I recommend to people taking the tour
Review provided by Viator
Salena_c
Apr 11, 2026
Amazing tour! Don’t miss... - Amazing tour! Don’t miss this!! So much fun and great information. Small group so very personal. Great host!
Review provided by Viator
Yoshihiro_i
Apr 5, 2026
Great fun! Enjoyed the... - Great fun! Enjoyed the enthusiastic and informative guide - the music playlist which mirrored the themes discussed in the tour also epic!
Review provided by Viator
Emily
Apr 4, 2026
Al Capone would be proud - Great way to see the city…especially on a cold, rainy day! “Marie” (Kate) kept the energy up and really embodied a prohibition era dame! Lots of fun would definitely recommend.
Review provided by Tripadvisor
Sunnydays44052
Apr 3, 2026
A Trip Back In Time - Winnie was amazing! She was an awesome storyteller and kept us amused throughout the 2 hour tour. I am a huge Al Capone enthusiast so learning more of his history in such a comical manner was perfect for me. I have taken a tour previously where we got on and off the bus so I enjoyed being able to just sit back and enjoy the ride. Winning the prize was also a plus as I planned to buy the book anyways.
Review provided by Tripadvisor
Discover24535452376
Mar 21, 2026
A lot of fun - Our guide was really fun and had a lot of knowledge of the monsters.it was a lot of fun
Review provided by Tripadvisor
Christopher_h
Mar 21, 2026
Fantastic tour, Marie was... - Fantastic tour, Marie was very knowledgeable and funny! Tour hit all the major sites from the history of the Beer Wars
Review provided by Viator
Martin_s
Mar 19, 2026
Gangsters paradise experience - Fun tour with fabulous and knowledgeable host, Marie. Also got to see parts of Chicago not seen on other tours.
Review provided by Viator
David_m
May 4, 2026
It's no 'Italian Necktie " - Tons of information and upbeat guide. I personally would have liked an opportunity to take a few pictures off the bus.
Review provided by Viator
Wendysgonewalkabout
May 2, 2026
A fun way to learn about Chicago's gangster history - We were looking for something fun and low-key for a somewhat chilly March day in Chicago -- this was perfect. The bus doesn't stop, it visits sites around Chicago and pulls over here and there for pictures and to tell a story, but you don't get off the bus. That's good for those who are less mobile! Make sure you go to the bathroom beforehand though. The guide (her stage name was Marie) was really good -- she told a good story, kept us entertained, occasionally made you roll your eyes at her accent, all the things that make a good gangster tour! A highlight for me was the drive by the Biograph Theater where Dillinger was shot. We watched Public Enemy in our hotel that night to bring it all home.
Review provided by Tripadvisor
From $48
up to 4 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).