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“Mallory was wonderful descriptive and enthusiastic. She made sure to connect with everyone and left no one behind :)”
3-4 hours of Chicago Prohibition lore and speakeasy stops on a guided walk or neighborhood bus tour. Drinks available to buy.
“Jonathon was a great tor guide. Had a lot of fun. And very informative. Would recommend to everyone! 10/10”
A 2.5-hour small-group walk through Chicago’s Prohibition-era streets and Riverwalk architecture, plus Chicago-style popcorn and lunch tips.
“Kelly, our guide, was phenomenal! We live in the Chicagoland suburbs so thought to take an official tour to learn more details than the obvious ones we already knew. Kelly fulfilled that with much knowledge, grace and charm. Had a wonderful tour and learned a lot!!!”
Chicago’s Prohibition-era vibe meets top Loop architecture on a small-group walk ending at Millennium Park’s Cloud Gate.
“The walk tour is something not to be missed for three reasons, especially when you’re on a short trip. Our guide, “tall Dave”, knows a lot about the history of the places we visited, shows interesting photos, and makes sure everyone is well accommodated. The sites have very fascinating architecture, some of them are hidden…”
Step into a 1929 speakeasy in Chicago for dinner plus a 90-minute twenties show with comedy and possible audience laughs.
“It was very unique! The staff was amazing and stayed in character the entire time. Heads up! It starts when doors open. This was our first speakeasy experience and we thought there would be a 15/30 minute seating window (as with other comedy shows). That wasn’t the case (apologies to the staff❤️). The food was…”
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.
