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Prohibition Cocktail Tour

Chicago, IL

Item #: LIF-CHI-0048
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Plunge into one of the most defining moments in American history as you sip your way through the Chicago Prohibition Cocktail 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.
  • The tour company has been featured in Chicago's The Local Tourist, in addition to being awarded the "Certificate of Excellence" from Trip Advisor.
River North Neighborhood - Chicago, IL
When Do I Choose A Date?
If giving as a gift, your recipient can choose a date at their convenience; otherwise, you can choose one after checkout.

June - September:
Friday through Monday - 4:00 PM

October - May:
Friday through Sunday - 4:00 PM

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  • All available dates have for this season have passed or sold out. Dates for the upcoming season will be posted as soon as they are available. To see a list of this past year's dates for your reference, please click here
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    Please select an option above.
    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
    Experience Provider Info
    Complete information for your Experience Provider, including contact information, will be included on your booking confirmation email once you or your gift recipient have scheduled the experience. Our Product Management team handpicks top-rated experience providers, removing the guesswork for you and ensuring your peace of mind.
    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.
    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.
    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.
    Are there any age restrictions?
    This tour is for guests that are 21 years old and older.
    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!
    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.

    Experience Vouchers that have not been redeemed can be returned hassle-free within 30 days.  All refunds will be made to the original purchaser.

    Experience Vouchers that have not been redeemed can be exchanged for anything else in our marketplace at any time.  If you choose to exchange for an experience that costs more, you'll simply have to pay the difference.  If you choose to exchange for an experience that costs less, you'll have a credit towards your next booking with Cloud 9 Living.

    Cancellation Policy

    Once you have scheduled a date and received a booking confirmation, all bookings for the Chicago Prohibition Tour are final.

    Customer Reviews
    (24 reviews)
    View More Reviews:
    “Elizabeth was great! Knowledgeable and fun, tying together prohibition, drinking and gangsters (inevitable given the timeframe) into a great story of Chicago through the era. Would definitely do again!”
    Response from Cloud 9 Living
    What a well said review! Our partners really strive to provide the best tour possible, and I'm glad you were able to reap the benefits of that! Looking forward to hearing from you next time you're looking for another 5-star experience! Cheers, Jake.
    “Fun time! Interesting topic that was covered in depth. My only complaint was that the tour got a little disorganized at the more crowded bars, but it was still fine.”
    Response from Cloud 9 Living
    Sweet! I'm so glad you were able to enjoy yourself fully during this wonderful tour despite some natural crowding at the more popular stops. Let me know next time you're looking to go out on another awesome experience! Best, Jake.
    “Fun & informative”
    Response from Cloud 9 Living
    Just like this review!
    “We had a great time learned a little about prohibition and we had a fun group!”
    Response from Cloud 9 Living
    Hi Dennis, That's just what we love to hear! I hope you found some new places to re-visit and made great new memories in Chicago! Cheers, Inah
    “Elizabeth was a fun tour guide.”
    Response from Cloud 9 Living
    Only the best for our customers!
    “Fascinating tour of Chicago's history throughout prohibition. Our tour guide Sydney was very knowledgeable and personable, and the tour was informative and such a fun time!”
    Response from Cloud 9 Living
    Hi Tommy, That sounds wonderful! Chicago has such a deep connection to the prohibition era and this tour does a great job of covering it. Thank you so much for sharing your experience, and we hope to get you out on another adventure soon! Warm Regards, Inah
    “tour leader very knowledgeable”
    Response from Cloud 9 Living
    A great guide for a great guest!
    “Exciting, fun, and VERY educational!! Fantastic tour guides!!”
    “My husband and I had a great time on this tour. We highly recommend our tour guide Sidney. We were amazed that we could laugh so much while learning so many interesting facts. All the bars had cool vibes and interesting drink selections. Definitely a great experience!”
    Response from Cloud 9 Living
    Hi Kris, Sounds like a great night out! And we agree, Sidney is definitely amazing. Good vibes and good drinks - what more can you ask for? Cheers, Inah
    “Very informative and super fun!”
    Response from Cloud 9 Living
    And a lovely review to boot! Cheers, Inah 
    “Sydney, the tour guide, is extremely knowledgeable mixed the perfect sense of humor. The bars/speakeasies we visited were great and had phenomenal drinks! Highly recommend!”
    Response from Cloud 9 Living
    Hi Ivette, first off thank you so much for taking the time to share your experience with us! We are so glad that you enjoyed all of the bars and speakeasies that you visited and that Sydney was able to help make your experience even better, I'll make sure to pass your kind words along. We hope you have a very Happy New Year!
    “Great history, lots of laughs, good drinks, interesting locations. We live in Chicago and we hadn't been to these places! A++”
    Response from Cloud 9 Living
    Hi Ryan, That's wonderful! I'm so glad to hear that even as a local, you were able to find new spots to visit. Let us know when you we can get you out on another memorable adventure! Cheers, Inah
    “This tour was incredible - lots of history shared, and really cool stories. Sydney was our tour guide, and kept our attention the entire time. She was very knowledgeable, hilarious, and really knew how to keep the group's interests. Very personable, made sure everyone was happy.”
    Response from Cloud 9 Living
    Hi Susan, Thank you for your kind words! I'm so glad you had a great time and I'll be sure to pass your compliments on to Sydney. Cheers to Chicago's storied past and delicious drinks!   All the best, Inah
    “Great tour! I thought the nature of the tour would cause it to be more directed at tourists, but the places and info are interesting to Chicago residents as well.”
    Response from Cloud 9 Living
    Hi Emerson, Thank you for your kind words! I know our guides take a lot of pride in showing off the hidden treasures of Chicago to locals, so I'll be sure to pass your compliments on to the team. Can't go wrong with good drinks and cool history! Cheers, Inah
    “This tour was a fabulous mix of history and alcohol. I loved the history, my husband and I both loved the drinks. Elizabeth did a great job of combining humor with the facts to keep everyone entertained.”
    Response from Cloud 9 Living
    Hi Kristine, I'm so glad to hear that! A little history, tasty drinks, and a fun guide - what a great way to spend a night. I hope you and your husband made some great new memories! Regards, Inah
    “The Prohibition tour is fantastic! Learning about the history of the bars, the bootleggers, and the gansters is so fascinating! Sidney the tour guide is amazing with her wealth of knowledge! She was so funny and made the trip amazing! The bars they chose to visit are unique, cool, and did a great job accommodating our large group. Highly recommend this tour, you will not be disappointed! The best weekend we’ve had in Chicago!”
    “Absolutely fun and informational. Sydney was amazing, and the drinks were great!”
    “I enjoyed the four visits and the historical knowledge provided by the guide was excellent. However, I must share my personal opinion about her use of "adult language." I have been an adult since long before Sydney was even a glimmer in her parents' eyes. I don't find it necessary to use vulgar language (the correct term for the language she used throughout) to make my point. Use of this style language has become all to common in today's society and is just further evidence of our loss of civility between human beings.”
    “Came with my wife as a birthday celebration. We are both interested in Chicago history and fine cocktails, and both aspects were well covered. The Green Door was probably the best stop on the tour, since it has a true speakeasy that still operates. We will definitely bring friends there. My only regret was there was not time to include the Green Mill on the tour too (too far north). The tour guide was very personable and well versed, and the other tour-ists were friendly. A fun time all around.”
    “Really enjoyed the experience -- very informative and fun. Our guide was fantastic. Would have been great to have drinks/samples included in the tour.”
    “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.”
    “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.”
    “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.”
    “The Prohibition Tour was really awesome. Our tour guide, Jonathan, was really knowledgeable.”

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