Chicago · PROHIBITION & SPEAKEASY TOURS
6 reviewed
Good prohibition & speakeasy tours fill up fast in Chicago, and the best fill up first. Here are the 6 to know, with current prices and what sets each one apart, so you can book before the calendar closes.
Chicago Prohibition speakeasy tour with 3–4 stops, guided history, and optional drink purchases, either walking downtown or by neighborhood bus.
“Johnathan was fantastic! We had such a fun time on the tour he was very informative. The three bars we ended in had great drinks too!”
A 2.5-hour Prohibition-era walking tour linking Chicago’s crime-era culture to stunning architecture, Riverwalk landmarks, and a popcorn treat.
“Excellent tour. Dash is very knowledgeable and taught us a lot. He’s very cognizant of the groups needs for breaks, restroom and snacks. He shows and educates us on local treats.”
Stroll Chicago’s Loop on a 2.5-hour Prohibition culture and architecture walk. See the Bean, Riverwalk, Wrigley and Tribune.
“Dash was an amazing host. So much information and history. He kept the group together even through the hectic parade. We had a wonderful tour. I only wish we had done Dash’s tour on our first day here”
Step into 1929 Chicago for a speakeasy dinner and 90-minute twenties revue with singing, comedy, and classic comfort food.
“It’s a Roaring Twenties experience with dancing and singing. There are also lots of jokes and gags with customer participation.”
Private 3-hour Chicago speakeasy VIP tour with historian-led secret entrances, luxury pickup, and Prohibition-era cocktails for up to 5.
“Alan, our host, was knowledgeable, kind and funny. He took us to great spots and made everything so fun. It was a huge hit with my group.”
Private 1920s Chicago speakeasy crawl with a local historian, secret entrances, and Prohibition cocktails for purchase. Hotel pickup included.
“At $330/person I was surprised that the operator/guide did not provide the drinks at the bars. He was very knowledgeable about the city and we had a great time. It was just too expensive.”
