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Chicago Prohibition Tour

  • 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 an entertaining guide
Chicago Prohibition Tour
From US$45.00
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  • Overview
  • What to Expect
  • Important Information
  • Reviews
  • Q&A
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Chicago Prohibition Tour
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.
What to Expect
Start your 3.5-hour Chicago Prohibition tour at the Green Door Tavern — 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.
Write a ReviewReviews (115)

1 - 5 of 10 reviews

Reviewed 1 week ago via mobile
Sydney rocks!

My adult sisters and my mom and I decided to try this tour because we enjoy history and local flavor. This tour is fantastic. Sydney, our tour guide, made this tour. She is funny, knowledgeable, personable, and well spoken. Be prepared for some language, but...More

Thank Kristina C
Reviewed 1 week ago
Fun Tour

This tour takes you all around the city of Chicago. We like food tours because they take you to parts of the city that you would not usually go and this tour was no exception. Fun to see some of the spaces that used to...More

Thank Jack P
Reviewed 4 weeks ago via mobile

We had a great time on this tour. Sydney was hilarious and very, very informative! Lots of great food and drinks were had by all. It's a great way to spend an evening.

1  Thank Shelley S
Reviewed 4 weeks ago
Fascinating Tour

Great Tour - I learnt a lot from a knowledgeable guide! I have to say the first 2 bars were Awesome you could see, hear and feel the history whereas the third felt like a corner store and the final one - no doubt had...More

Thank Kylie H
Reviewed 30 May 2018
Excellent Tour

Visited 4 of the bars where it actually happened in the care of a very knowledgeable guide and learned a mountain of information about the prohibition movement as well as the actual prohibition era. Interestingly it exploded quite.a few of the common myths exported in...More

1  Thank jmg1939
Questions & Answers
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24 July 2018|
Response from Shelley S | Reviewed this property |
There are four stops so at least $60 for drinks, more for food. I think we spent about $100.
Tammy M
16 June 2018|
AnswerShow all 3 answers
Response from Sherry B | Reviewed this property |
4:00 to 7:30