• Location: Chicago, Illinois
  • Duration: 3 hours 30 minutes (approx.)
From USD $ 45.00 View price calendar

Low Price Guarantee

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 an entertaining 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 Our Insiders Chose This Tour

What You Can Expect

Chicago Prohibition Tour

See antiques used during the prohibition era.era.

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.

Customer Reviews

Kathy W

5 star rating: Highly Recommended April 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

5 star rating: Highly Recommended March 2018

This tour was amazing!


5 star rating: Highly Recommended March 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!

Jennifer S

5 star rating: Highly Recommended February 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!

Brett W

5 star rating: Highly Recommended February 2018

This tour was amazing!

Robert R

5 star rating: Highly Recommended January 2018

Great tour, great guide. This was worth every penny.

Jason A

5 star rating: Highly Recommended January 2018

Sydney was a great tour guide and we had a lot of fun!!

Gaetana D

5 star rating: Highly Recommended January 2018

This tour was fantastic. We loved the history, the host - jonathon you rock, and the venues too. Perhaps one thing that could be cool is some kind of written synopsis of the history you told that could be grabbed at the end. Not to take away from but to enhance the tour. Thanks again :)

Wendy C United States of ... 

5 star rating: Highly Recommended December 2017

We really enjoyed this tour! Loved hearing the history of each bar we visited. I do wish they would've included a free signature drink at each one but we still had fun. Would definitely recommend doing this!!

Greg T

5 star rating: Highly Recommended December 2017

We loved this tour, giving us the opportunity to visit 4 different venues all unique with their own background and stories. So good to see them all still running today, each place was very busy.
Our guide was very knowledgeable and informative, sharing history and answering questions along the way.
Was great to see the variety of venues and enjoy with time for a couple of drinks at each place, some ofvtheparticipantscalsonhadvtime to order yummy food. We met some great people on the tour, from all over the world .
The meeting place The Green Door was easy to find ,we walked from our hotel, the hidden tunnels, back rooms andcsecret passageways were very cool and the stories were fascinating.
We discovered the Moscow Mule and have been enjoying this drink ever since back home , a great reminder of an awesome tour.
At the end of the tour in the city last stop was a busy bustling restaurant that serves AMAZING pizza pie , so we stayed there for tea , this stop was central and easy to walk back to our hotel, or near the train and bus stop if needed.
We loved the two stops in the middle as they were out of the city and in suburbia, our guide also explained these areas, and we loved seeing these areas of Chicago , so an additional bonus.
Overall this was very well organised, interesting and lots of fun , have encouraged others to do this tour , they have and loved it as well :-
Happy travels people !!
Cheers from Australia

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