Prohibition Walking Tour
Duration
2 hour(s)
Languages
English
Skip the line
Included
Explore hidden speakeasies and secret bars throughout city streets
Discover underground haunts where rebels defied prohibition era laws
Pass historic homes of legendary Hollywood figures in neighborhoods
Learn stories of powerful organizations controlling citywide alcohol trade
€ 48.94
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Step back in time to the Roaring Twenties on this immersive Prohibition Walking Tour. Wander through the city streets where hidden speakeasies, secret bars, and underground haunts reveal the rebellious spirit of an era defined by bootleggers and social intrigue. Along the way, you will pass historic homes of Hollywood legends who mingled with some of the most notorious figures of the time. Your guide shares captivating stories about the powerful political organization that shaped the city, controlled illegal alcohol trade, and influenced citywide corruption. Each stop highlights the clever ways people kept the party going while avoiding the law, giving visitors a glimpse into a fascinating period of history.
At each location, enjoy a drink inspired by the Prohibition era, crafted in the style of those who celebrated in secrecy. This tour offers the perfect combination of history, storytelling, and flavorful beverages, allowing guests to experience both the cultural and social sides of the 1920s. The walk balances informative commentary with entertaining anecdotes, keeping the tour engaging and memorable. Whether you are a history enthusiast, cocktail lover, or simply curious about the hidden stories of the city, this experience delivers a lively and educational journey through one of the most exciting periods in American history.
Guided walk historic streets
Visit iconic New York bars
Stories bootleggers rebels political figures
Explore Hollywood legends homes era
Learn powerful political organization influence
Drink tasting at each stop
History fun anecdotes Roaring twenties
Additional food or drinks (outside of those provided at each stop)
Hotel pick-up or drop-off
Personal expenses
Gratuities
Valid ID or Passport
Comfortable walking shoes
Weather-appropriate clothing
Water bottle
Small bag or backpack
Umbrella or rain jacket
Camera or phone
Please arrive 15 minutes before the tour start time to check in
Must be above 21 for alcoholic beverages
Tour is outdoors so weather may affect experience
The tour includes visits to bars that serve alcohol, please drink responsibly
Confirmation will be received at time of booking
Type in your hotel/accommodation to see how far the attraction or departure point is.
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Activity Provider: Forty Thieves Tours
Customer Reviews
Sherie
This was hands down one of the funnest tours I've ever been on. Johnathan is very knowledgeable & entertaining. I loved all the history and fun facts. And what's not to love about having some cocktails while being bussed around & learning some new stuff. It is well worth the money and the time flys by when you're having fun! I highly recommend it. And I would definitely do it again.
Erica
A Must-Do in Chicago! 10/10 Jonathan was an incredible tour guide—knowledgeable, funny, and full of energy! He had a great way of weaving stories together that kept the entire tour engaging and memorable. His mix of history and humor really brought the Prohibition era to life. This was our first time visiting Chicago, and booking this tour was my idea. I'm happy to say my whole family absolutely loved it! We even capped off the experience with a meal at Harry Caray’s afterward, which was the perfect ending. If you're in Chicago and have some free time, definitely take the Prohibition Walking Tour. You won’t regret it, such a fun and fascinating way to explore the city!
Jon
AMAZING!! Took my wife for our anniversary/ her birthday. We did the original bus tour. Jonathan was extremely knowledgeable, funny, and easy-going, and he kept the entire tour engaging. Each stop was unique and had great drinks. Take advantage of the opportunities to eat when you can. They are worth it. Highly recommend the tour for couples and even more so for larger groups. Can't say enough good things about this!
Su
We had the best time yest. on this walking tour with Jonathan K. The history and knowledge makes it a great tour…even his personality could be worth an extra star😉. You can take any tour but pay to take a tour with ones that are passionate about what they do. It’s well worth it & the places you visit also appreciate these people. Remember to tip your hosts and servers well📣
Liezl
Went on the Original Chicago Prohibition Tour (bus tour) with a bachelorette party. Our group had a great time. We went to four different locations, in photos, and were surprised at how much we learned on the tour. The locations we visited were fun and had great drinks. We even had time for a quick food break at one of the locations. Our guide Jonathan was very informative and made the learning fun. As Chicago-suburb locals, it was fun to learn about the city we grew up near. We would definitely consider going on it again!