Chicago Prohibition Tour

From: $45   


River North Neighborhood - Chicago, IL


Saturdays & Sundays - 4:00 PM

Fridays, Saturdays & Sundays - 4:00 PM

Plunge into one of the most defining moments in American history as you sip your way through the Chicago Prohibition Tour!
  • Visit the city's most iconic former speakeasies, and enjoy favorite drinks from the 1920s and 1930s.
  • As a 3.5-hour tour, you'll enjoy taking in some light Chicago sightseeing and attractions as you traverse from venue to venue.
  • Discover the colorful history behind the Prohibition era and the notorious characters that played pivotal roles in its story.
  • Whether a local or visitor to the Windy City, this late-afternoon Chicago city tour is the perfect way to ease into an evening out with family and friends.
  • The tour company has been featured in Chicago's The Local Tourist, in addition to being awarded the "Certificate of Excellence" from Trip Advisor.

More detailed description >

Tantalize your taste buds with suds of the past! Enjoying vintage drinks at various speakeasies, while learning fun facts about one of America's most famous eras all on the Chicago Prohibition Tour.

Immerse yourself in a "sip of history" on this enticing 3.5-hour tour of Chicago's most renowned former speakeasy locations. Your experienced and knowledgeable guide will engage you in the enthralling facts and stories behind this pertinent era of U.S. history.

At each stop along the way, learn how the particular venue and its surrounding neighborhood played a part in the Prohibition events that shaped the Windy City. Let your imagination run wild as you're told tales of the notorious people who played pivotal roles in how the Prohibition unfolded whether by enforcing or breaking the 18th Amendment. Learn about its repeal and the 'revolution' that followed.

But don't let your experience of the Chicago Prohibition Tour stop there! Go beyond this alluring food for thought and treat yourself to cocktails that were a part of this era's law and liberation concerning libations! At each speakeasy stop, your tour guide will be sure to recommend signature cocktails that either come with a bit of vintage flair to commemorate the Prohibition, or that are most popular among today's modern patrons.

Stops featured along the way on this Chicago city tour are subject to change, but may include:

  • Downtown tavern built in 1872
  • Wicker Park lounge
  • Friendly neighborhood bar in Old Town
  • Downtown area restaurant, along the Loop.

So raise a glass and toast your neighbor be it a friend, family or fellow tour-goer! Because on top of being a most memorable outing, the Chicago Prohibition Tour serves as a delightful reminder that the dry days are long gone, and drinks should be shared! Cheers!

Key Info >

Essential Information:

  • Participants will be transported by bus to 4 different locations
  • Must be over the age of 21 with a valid ID to enjoy this experience
  • Food and drinks are not included in the price of the Chicago Prohibition Tour
  • Gratuity for your guide is not included, but is greatly appreciated if you enjoy your tour
  • The starting point is about 1.5 miles from the ending point, and returning transportation will not be provided. Directions will be provided if needed and local public transportation is available.

3.5 hours

Maximum Participants:
Up to 20 people on the tour.

This experience is for booked participants only.

Weather Dependent:
This experience is not weather dependent.

What to Wear:
Wear comfortable clothes appropriate for the weather.

Booking Information:
For this experience, it is recommended to request bookings at least 14 days in advance of intended date of use.

Cancellation Policy:
Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have scheduled a date and received a booking confirmation, all bookings for the Chicago Prohibition Tour are final.

Experience ID:

View FAQ's >

  1. Are drinks included in the price?
    Your guides will recommend drinks to be purchased at each stop. The price of your beverages, any snacks and gratuity for waitstaff are not included.
  2. Does the tour end at the starting location?
    Your tour will end about 1.5 miles from the starting point. Transportation back to the starting point will not be provided, but local public transportation will be available nearby.
  3. Are there any age restrictions?
    This tour is for guests that are 21 years old and older.
  4. What should I bring?
    Please bring cash for any drinks you would like to purchase on the tour and a government issued, valid form of ID. You might want to bring your camera as well to capture the fun experience!
  5. What is included?
    On this tour, you'll get to take a step back in time and see the way Chicago operated nearly 100 years ago during the prohibition era. Your tour guide will educate you on the history of prohibition while you explore the speakeasies of Chicago by bus.

Customer Reviews:

  • Chicago Prohibition Tour

  • July 18, 2016

  • 5

  • Chicago

"I am a Chicago resident and I was impressed with both the knowledge and forum selection for the tour. The Prohibition Tour is definitely a keeper."

  • Chicago Prohibition Tour

  • October 07, 2015

  • 3-half

  • Chicago

"I felt the price for the experience was expensive. The price included the guide and a bus ride to 3 bars within a 3 mile radius. A ride back to where we started and where our car was parked was not provided. The guide was very knowledgeable about the history of the Prohibition, but I felt she did not do anything to get the group to get to know each other. Everyone just minded their own business and sat with the party they came with. I think it would have been more fun if she (Sydney) would have got the group talking to each other. She was young (just turned 21) so maybe she just needed more experience working with a group of people. I was amazed at her speaking ability. She really was a good speaker, but gave us a lot of information which was hard to process after a few drinks. The information was interesting but I got lost at times because of the vast amount. With a few changes, I think it would be a really fun experience."

  • Chicago Prohibition Tour

  • July 06, 2015

  • 4

  • Chicago

"While it was acknowledged that there may be profanity used throughout the tour, I truly did not feel it was necessary nor did enhance the experience in anyway. Also, the 21-year-old guide just didn't pull off the use of the profanity with much finesse, so why bother."