


Prohibition Walking Tour
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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
Explore The Secret Speakeasies And Rebellious History Of The Roaring Twenties Era
Step back in time to the Roaring Twenties on this immersive Prohibition Walking Tour. Wander through 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, providing a unique window into the glamorous and dangerous lifestyle of the decade.
Your guide shares captivating stories about the powerful political organizations that shaped the city, controlled the illegal alcohol trade, and influenced widespread 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 American history. 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.
At each location, enjoy a drink inspired by the Prohibition era, carefully crafted in the style of those who celebrated in secrecy. The walk balances informative commentary with entertaining anecdotes, keeping the tour engaging and memorable for every guest. Whether you are a history enthusiast, a cocktail lover, or simply curious about the past, this experience provides a deep dive into the era that changed the social landscape of the country forever.
The tour winds through significant locations, ensuring you see the sites where history was made and secrets were kept. By combining historical facts with the atmosphere of the era, the tour creates a vivid picture of life during Prohibition. Join us for an unforgettable journey through the shadows of the past, where every corner tells a story of defiance, innovation, and the enduring spirit of a city that refused to stop celebrating.
Explore The Secret Speakeasies And Rebellious History Of The Roaring Twenties Era
Step back in time to the Roaring Twenties on this immersive Prohibition Walking Tour. Wander through 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, providing a unique window into the glamorous and dangerous lifestyle of the decade.
Your guide shares captivating stories about the powerful political organizations that shaped the city, controlled the illegal alcohol trade, and influenced widespread 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 American history. 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.
At each location, enjoy a drink inspired by the Prohibition era, carefully crafted in the style of those who celebrated in secrecy. The walk balances informative commentary with entertaining anecdotes, keeping the tour engaging and memorable for every guest. Whether you are a history enthusiast, a cocktail lover, or simply curious about the past, this experience provides a deep dive into the era that changed the social landscape of the country forever.
The tour winds through significant locations, ensuring you see the sites where history was made and secrets were kept. By combining historical facts with the atmosphere of the era, the tour creates a vivid picture of life during Prohibition. Join us for an unforgettable journey through the shadows of the past, where every corner tells a story of defiance, innovation, and the enduring spirit of a city that refused to stop celebrating.
- 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
$ 89
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Activity Provider: Forty Thieves Tours
Customer Reviews

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.

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!

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!









