Tours and Tickets
Chicago Prohibition Tour
4.5

Chicago Prohibition Tour

By Chicago Pizza Tours
Recommended by 96% of travellers
96% of reviewers gave this product a bubble rating of 4 or higher.
About
If you're a fan of the not-so-typical history tour where you can learn about gangsters, bootleggers, and cops, then don't miss this Chicago Prohibition tour. Sit back as you're whisked to some of the city's historic bars and speakeasies, where you can buy a drink or two, learn about famous mobsters like Al Capone, and hear about the sobering decade when alcohol was banned in the United States.

Ages 21-99, max of 20 per group
Duration: 3h 30m
Start time: Check availability
Mobile ticket
Live guide: English
More

Highlights
  • Learn about Prohibition-era Chicago on this adults-only speakeasy tour
  • Visit four different historic bars, including a steakhouse built in 1872
  • Enjoy a more personal tour experience, with no more than 20 tour guests
  • Get a great value with guide, air-conditioned travel, and bar entry included

  • Air-conditioned vehicle
  • Live commentary on board
  • Professional guide
  • Printed guide to follow along with drink recommendations.
  • Entry/Admission - Wicker Park
  • Entry/Admission - Chicago River
  • Entry/Admission - The Loop
  • Entry/Admission - The Old Town of Chicago
  • Entry/Admission - Lincoln Park
  • Entry/Admission - Chicago
What's not included
  • Gratuities
  • Food and drinks (available for purchase)
  • Hotel pickup and drop-off


Start:
  • Harry Caray's Italian Steakhouse, 33 W Kinzie St, Chicago, IL 60654, USA
    When you arrive, please go inside to meet your guide.
End:
  • Option 1
    Exchequer Restaurant & Pub, 226 S Wabash Ave, Chicago, IL 60604, USA
    Friday/Saturday/Sunday Tours end at Exchequer which is located on Wabash Ave not far from The Art Institute.
  • Option 2
    Butch McGuire's, 20 W Division St, Chicago, IL 60610, USA
    Monday tours end at Butch McGuire's which is located just north of the starting location in The Gold Coast.

  • Not wheelchair accessible
  • Near public transportation
If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 5552PROHIBIT

  • Confirmation will be received at time of booking
  • Minimum age is 21 years
  • Most travellers can participate
  • This tour/activity will have a maximum of 20 travellers

  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 5552PROHIBIT

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Itinerary
  • You'll start at
    Harry Caray's Italian Steakhouse
    33 W Kinzie St, Chicago, IL 60654, USA
    When you arrive, please go inside to meet your guide.
    See address & details
  • 1
    Wicker Park
    Stop: 45 minutes - Admission included
    See details
  • 2
    Chicago River
    Stop: 45 minutes - Admission included
    See details
  • 3
    The Loop
    Stop: 45 minutes - Admission included
    See details
  • 4
    The Old Town of Chicago
    Stop: 45 minutes - Admission included
    See details
  • 5
    Lincoln Park
    Stop: 45 minutes - Admission included
    See details
  • 6
    The Gold Coast Realtor
    Stop: 45 minutes - Admission included
    See details
  • You'll end at
    See departure details
About the operator
Don’t take it from us – here’s what people have to say about this operator:
  • Chicago Pizza Tours
    603
    Chicago, United States
    Joined in May 2010
  • Jean H
    0 contributions
    5.0 of 5 bubbles
    Witty and wonderful
    Wow. What a great way to taste the history of pizza in this town. We chose this one mainly because the weather was slated to be windy and rainy, and the allure of bus transport in those conditions. We hit the jackpot. We learned so much about the origins of the Chicago styles of pizza - deep dish varieties, tavern thin crusts, and coal-fired. The personal history stories and the humorous and sometimes downright hilarious banter of James, guide extraordinaire, topped off a delicious dive into pizza. And being on a bus meant we could literally cover more territory, experience more establishments, and see more neighborhoods than we could have covered on foot. Didn’t miss the behind-the-scenes stuff due to the thoroughness of James’ narration. In a heartbeat, highly recommend.
    Written 10 March 2024
  • Ejpjap
    0 contributions
    5.0 of 5 bubbles
    Great!
    The tour was fun. James was a great guide. It was interesting listening to his stories. Pizza was delicious!! Can’t recommend this tour enough!
    Written 11 February 2024
  • Cpatravels
    0 contributions
    5.0 of 5 bubbles
    Fun experience
    Lots of pizza and lots of information about pizza. Enjoyed the group but pace yourself. There were lots of leftovers at each place so by the time you get to the last place you’re beyond stuffed!
    Written 1 February 2024
  • I7922BZgeorget
    0 contributions
    5.0 of 5 bubbles
    Delicious and fun!
    This was one of the best tours we’ve ever done. The pizza was great, and our tour guide James was so much fun. You get highlights of a few neighborhoods at the same time. We will likely do this again when we return, and recommend this to any pizza fans out there.
    Written 28 January 2024
  • subieb2015
    0 contributions
    5.0 of 5 bubbles
    Highly recommend
    Fun! Fabulous Pizza! James was a great guide and was able to accommodate special needs. Entertaining as well!
    Written 22 January 2024
  • S5113KUmarym
    0 contributions
    5.0 of 5 bubbles
    Nice
    It was a very good trip the first three pizza places was excellent Flo&Santos was the best The last place was the worst
    Written 12 November 2023
  • tekeys1
    0 contributions
    5.0 of 5 bubbles
    Delicious Cheesiness
    My mom and I took this tour on 11/4. We had such a great time learning and tasting our way through all the many pizza types Chicago has to offer! The tour was well thought out, organized and very entertaining. You're stuffed at the end with a smile on your face!
    Written 6 November 2023
  • Victoria R
    0 contributions
    5.0 of 5 bubbles
    Excellent
    Excellent tour, very interesting and ALL the pizza was delicious. We saw this as a must when visiting Chicago and did not disappoint. We attended with our 4 year old which was no problem at all and he loved all the pizza on offer.
    Written 5 November 2023
  • Chris W
    0 contributions
    5.0 of 5 bubbles
    A Chicago MUST DO event
    James our tour operator was so engaging and knowledgeable. He made the 3.5 hours go by quickly. 4 different pizzas in 4 different neighborhoods is just the right number. He held our attention the entire time with interesting historical information and jokes. The amount of food was a normal serving size with an opportunity for seconds! This is a Chicago MUST DO event!
    Written 26 October 2023
  • angebruni
    0 contributions
    5.0 of 5 bubbles
    A MUST DO!
    This was an awesome way to explore the many pizzas of Chicago, which is not just deep dish! James was the best tour guide - super knowledgeable, passionate, shared fun facts about Chicago and SO funny!! Highly recommend this tour and remember to pace yourself!
    Written 25 October 2023
  • Dodgegirl3500
    0 contributions
    5.0 of 5 bubbles
    Best experience EVER!
    Tour guide? TOP NOTCH! Bus driver? TOP NOTHCH! Pizza? TOP NOTCH! Learning about the history of pizza in Chicago? TOP NOTCH! I am now ruined and will never be able to enjoy pizza in my small southern town again! The atmosphere provided was so friendly, funny and welcoming. And by the end, I felt like everyone else on the tour was a close friend. The vibes were immaculate. If you're even considering this tour, DO IT! You won't regret this at all. Only complaint? That I didn't have another stomach to be able to finish alllll of the pizza!
    Written 23 October 2023
  • deba192
    0 contributions
    5.0 of 5 bubbles
    Pizza and History
    Not to be missed walking tour. Try 4 different styles of pizza and learn all about the restaurateurs and their process. Jon is a wealth of information and can fill you in on local Chicago history as well as pizza.
    Written 21 October 2023
  • bmh86
    0 contributions
    5.0 of 5 bubbles
    Such a fun and delicious experience
    The pizza was amazing! I really enjoyed trying the different styles of pizza. I liked both the deep dish and the thin crust. I think my favorite might have been the coalfire pizza but they were all delicious. I was so full by the last stop. Our guide, James, was hilarious. He did such an awesome job! The only thing that could have been better was the meeting point. It was a bit confusing where in pizano's you were supposed to go. But overall it was such a great experience. I know my friends also had a fantastic time!
    Written 11 October 2023
  • A5670JUkarenl
    0 contributions
    5.0 of 5 bubbles
    Wonderful tour!
    We had a great time on the tour. Very informative and entertaining. We really enjoyed trying 4 types of pizza.
    Written 8 October 2023
  • Jeremiah P
    0 contributions
    5.0 of 5 bubbles
    Good Times!
    We love pizza, so it was a must on our anniversary trip here to Chicago, very informative, a nice walk around the part of city we were in, pizza was great at all places and the guide was super nice and down to earth, we highly recommended this particular tour.
    Written 7 October 2023
See all 603 reviews
These reviews are the subjective opinions of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

Popular mentions

4.5
4.5 of 5 bubbles54 reviews
Excellent
43
Very good
9
Average
1
Poor
1
Terrible
0

Steven H
Vancouver, British Columbia2 contributions
5.0 of 5 bubbles
Jun 2023
This tour was equal parts fun and entertaining.

As a sober person who does not consume any alcohol I was a little nervous, however, I had a blast and was able to try different types of mocktails.

Truthfully the tour is less about the consumption of alcohol and more about history but the spots we were taken too have amazing selections of various drinks.

Would do again in a heartbeat!
Written 26 June 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

dianegTNgirl
Nashville, TN62 contributions
5.0 of 5 bubbles
Nov 2018 • Couples
This tour was so much fun. Elizabeth was an excellent tour guide and gave us lots of information and history in a fun relaxed atmosphere. She was very helpful and friendly, told us what to try at each stop. The drinks were strong and delicious, and I felt like I got a peak into the everyday Chicago life at these locations. Really learned the real background of prohibition, and had fun doing it. Book this tour...you won't be disappointed.
Written 13 November 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

daveamiet
Brisbane Region, Australia22 contributions
5.0 of 5 bubbles
Jul 2018 • Couples
A really excellent tour with a great guide who was extremely friendly and highly organised. She had an amazing and detailed knowledge of the history of Chicago and especially of the prohibition era. We visited 5 prohibition era sites and enjoyed our time at each...especially the Green Door Tavern which was the most authentic with a wonderful old time atmosphere. We had time at all locations to enjoy some snacks and try some interesting drinks....especially the Jameisons with Pickle Juice!!! We would highly recommend this tour especially if one is interested into gaining an insight into Chicagos history and it's somewhat shady and often violent past.
Written 2 October 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

NewOrleansTravel
New Orleans, LA22 contributions
5.0 of 5 bubbles
This was an amazingly informative tour. Hubby likes history and Sydney did a great job at explaining the period and how all the characters fit together. Lots of history but explained in a fun way that makes you feel like you are living it. The bus used for transportation was really nice too. But one of the things that impressed me the most was their customer service. The tour is supposed to be 3 hours. We caught really bad traffic between the first and second bar. Other tours would have tried to make up time by shortening the amount of time spent at each of the locales - they did not do that! They asked if anybody needed to rush and since we were all ok, they just went at the same, regula pace. We finished almost 1 1/2 hours later than it should have been but both Jonathan (driver) and Sydney just hang around and continued as if nothing had happened and they were just hanging around with friends. If you are on the fence between this and another prohibition or gangster tour, definitely take this and enjoy the tour!
Written 27 January 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

dugyoda
Wellington, New Zealand24 contributions
5.0 of 5 bubbles
This tour greatly exceeded my expectations. The tour guide was very good and provided a great deal of information about how prohibition came about and how it ended in a very entertaining way. The group were soon chatting to each other once we had our first cocktail. All 3 bars were excellent.
I had a cocktail at the first and local IPA beer at the other two. The tour finished about 8pm and I walked the 20 minutes back to my hotel. Others used Uber.
Written 23 July 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Christina P
Tinley Park, IL48 contributions
4.0 of 5 bubbles
Feb 2020
Enjoyed a fun night in the city on the Prohibition Tour with Elizabeth. As history buffs and fans of trying new drinks - it was a perfect combo. There are things you should know that might help your decision to book this tour. You do some standing - while Elizabeth is giving the history at each speakeasy, you stand in a spot in the room where waiters and waitresses frequently pass by. She doesn't have a microphone, so at times, it is hard to hear and concentrate on what she is saying. She does a lot of speaking on the bus. Each stop had it's own wonderful vibe, and you'll want to try a drink at each one. The drinks run about 10-15 dollars, and there are some good appetizers to be had. Finally, the last stop is not where you start the tour, so you will need to walk or cab back to the first stop after the tour. All this being said... a night out in Chicago is magical - and this tour spotlighted some wonderful places.
Written 2 March 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Gina Redward
New Zealand5 contributions
5.0 of 5 bubbles
Dec 2019 • Couples
Our tour with Connor was excellent. It was great mix of history and the paranormal and a chance to explore some of Chicago's more haunted locations.
Written 13 December 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

leasesd
San Diego, CA28 contributions
5.0 of 5 bubbles
May 2019 • Solo
Sydney was awesome! I highly recommend this tour. The driver was entertaining as well and kept us laughing. Great cocktails and great bars with a history lesson to boot. Who knew that the answer to all things Chicago isn't Al Capone ?!!?!?
Written 24 May 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Kathy B
Crown Point, IN6 contributions
4.0 of 5 bubbles
Jul 2018
It was a great Tour. The drinks were good, but eat before you go, there isn't enough time to eat while touring.
Written 4 October 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Jack P
Puako, HI29 contributions
4.0 of 5 bubbles
Sept 2017
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 be speakeasys and you are at each place for enough time to have a cocktail and a bite.
Written 6 August 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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Chicago Prohibition Tour provided by Chicago Pizza Tours