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Chicago Prohibition Adults-Only Tour of Historic Speakeasies

Cook County, United States
Book online or call: (888) 651-9785(888) 651-9785

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3 hours 30 minutes (Approx.)
Mobile ticket
Offered in: English


Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
  • Visit bars in the Old Town district, Wicker Park, and the Chicago Loop
  • Learn about cocktails that date to the 1920s
  • Enjoy a fun and informative historical tour led by a professional guide
  • Hear about the crime syndicates of Chicago’s most notorious scofflaws, including Al Capone
  • Understand the roots of the temperance movement that led to Prohibition and its consequences

Why Travelers Choose This Tour

You'll be whisked off to four bars that can be tough to find on your own, with a bus to easily shuttle you between each and act as your designated driver. Since the tour doesn't end where it begins, arrange for transport to your next stop or be prepared to hail a cab.
Start your 3.5-hour Chicago Prohibition tour at Harry Caray's Italian Steakhouse — a vintage downtown bar built in 1872 and decorated with antiques and Americana collectibles that give it a sense of old-time Chicago. Be sure to bring along your government-issued ID and some cash to purchase craft cocktails and signature drinks made by expert bartenders on this adults-only tour.
Your entertaining guide illuminates the underground world of Chicago’s historic speakeasies used during Prohibition and still in operation today. Learn why the sale of alcohol was banned in the US from 1920 to 1933, and discover Prohibition’s key players. Hear anecdotes about lawbreakers like Al Capone and other Chicago mobsters who became powerful during the dry years.
A coach shuttles you between four establishments, each with a different character. Pull up a stool at a cocktail lounge in Wicker Park where great blues music pumps from an old jukebox. You'll also enjoy a neighborhood bar that claims to be the oldest and longest-running tavern in the Old Town district.
Wrap up your Chicago speakeasy tour at Exchequer Pub, a Chicago Loop restaurant where historic photographs and posters line the walls of the decades-old bar.

Traveler Photos


Viator Traveler's Reviews

109 Reviews
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Karen H
, Jan 2019

This was the best tour we have ever been on! Sydney knocked it out of the park. Not only is she knowledgeable about the history of prohibition in Chicago, she is incredibly witty and customized the experience to ensure everyone was having a great time. We are already planning on taking the tour again with more friends and family members. This is truly a "can't miss" Chicago experience!

, Sep 2018

Elizabeth was our guide and she did a great job. She was very personable and made the tour fun. We enjoyed each stop along the way. I would definitely recommend this tour if you are in Chicago.

, Aug 2018

Sidney is probably the most entertaining tour guide I've ever had. Lots of laughs, good drinks, and learned some stuff to boot. Highly recommend.

Rebecca K
, Aug 2018

We had Sydney as a guide, and she was fantastic. She knows her history, she was fun, and the tour was great.

Jill F
, Jul 2018

This is fun tour --education and cocktails! Definitely for adults with a sense of humor only as some of the presentation is

Kathy W
, Apr 2018

We had an amazing tour with Sydney! Extremely knowledgeable and a lot of fun. Learned many interesting tidbits about Prohibition and thoroughly enjoyed our tour. Martinis at Club Lucky are the best! Thanks for a great afternoon, we highly recommend it.

Elizabeth B
, Mar 2018

This tour was amazing!

, Mar 2018

A great experience - took this tour in the middle of winter and it was a blast. The bus provided is a great asset and is pulled up to the door of each establishment. The cocktails were excellent and it's easy to make new friends and find a few gems to re-visit after the tour. Cheers!

Judy A W
, Mar 2018

Of all my Viator trips over the years abroad, this is the first tour that disappointed me. First, the tour guide. During the bus rides she had a lot of very interesting information. However she spoke very fast, with her volume lowering at the end of sentences. With so much good information the tour would seem more substantial if speaking more slowly and using a mic. Second, in just about her first sentence about the history included the word "f***ing" and shortly after that, "a**hole." Now this was funny at first. However she used these and similar expletives more often after each drinking stop until the last bus segment was "f***ing" everything. She also seemed to think it was part of the comradery and added humor to call a couple of the tourists "a**hole." REALLY? Maybe she doesn't hold her liquor well. I think she sees herself as one of those stand-up comedians whose audience comes to the theater to be insulted. It was a bore, at the least.
The tour itself - The information on the bus sans the language issues was very good. The first bar stop was excellent. The next stops went progressively downhill until the historic information inside the last bar was five minutes standing in the entrance to the packed dining room, dodging waiters and diners and trying to hear. And very little actual historic elements to see. My advice is to skip that bar and save the best first one for last. And change the guide.

Jennifer S
, Feb 2018

The tour was great!! The guide was amazing, full of knowledge and very funny. Really gave us a complete picture of prohibition. We also enjoyed some.great drinks!

Product code: 5552PROHIBIT

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