CHICAGO · ILLINOIS
The best of Chicago.
The 7 best prohibition & speakeasy tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Booze and Boos takes you through Lincoln Park pubs and ghost lore in about 2.5 hours with a costumed guide and drink stops.
Most Popular“We had fun and learned a lot about the city. Very informative with a little bit of alcohol involved. Lara & Brandon did a great job!”
3-4 hours of Chicago Prohibition lore and speakeasy stops on a guided walk or neighborhood bus tour. Drinks available to buy.
“Really really interesting tour… very informative Lots facts… more a history tour than a walking tour and we enjoyed it very much!”
A 2.5-hour small-group walk through Chicago’s Prohibition-era streets and Riverwalk architecture, plus Chicago-style popcorn and lunch tips.
“Dash was a fantastic tour guide. He found lovely sights for the the group that were gems to be shown and to re-visit. I would highly suggest thistiur in Chicago. 🩷💙💜💛💚🧡🤍🩶”
Chicago’s Prohibition-era vibe meets top Loop architecture on a small-group walk ending at Millennium Park’s Cloud Gate.
“David was very engaging and clearly excited to show off the city. I was however disappointed with the itinerary. I was hoping to see more architecture (Wrigley building, Tribune tower, NBC building, Flamingo sculpture, etc. Instead, we spent way too much time in Marshal Fields and buying pop corn.”
Step into a 1929 speakeasy in Chicago for dinner plus a 90-minute twenties show with comedy and possible audience laughs.
“Be ready for a lot of interactions and laughs. There was never a dull moment from the time we walked in, til we walked out.”
A 3-hour private VIP Chicago speakeasy tour with secret entrances, preserved Prohibition-era bars, and luxury transport for up to 5.
“Great tour guide and very fun experience.”
Private 1920s Chicago speakeasy pub crawl with a local historian, secret entrances, hotel pickup, and optional Prohibition-era cocktails.
“Stefan was an excellent Guide with lots of historic knowledge. The venues were interesting and not something we would have been able to find on our own.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
