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Explore Chicago’s secret speakeasies with a private guided tour that mixes history and signature drinks. Discover fascinating stories from the Prohibition era while tasting iconic cocktails across four hidden bars.
Explore Chicago’s secret speakeasies with a private guided tour that mixes history and signature drinks. Discover fascinating stories from the Prohibition era while tasting iconic cocktails across four hidden bars.
Book with Chicago Prohibition Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Chicago Prohibition Tours · Chicago, Illinois
easy.
3.5 hours.
Suitable for all fitness levels; involves moderate walking between stops over mostly flat urban terrain.
Yes, the tour is perfect for private groups, couples, and small parties looking for an intimate experience.
The tour includes tastings at each speakeasy, but you can also order additional drinks at your own expense.
Since this is primarily a cocktail tour, please communicate any special dietary needs to your guide in advance.
Some locations may have limited accessibility due to historic building layouts; please inquire when booking.
Smart casual and comfortable shoes are recommended since you’ll be walking between venues.
The speakeasies are within close walking distance, typically just a few blocks apart in neighborhood settings.
Chicago's Prohibition era saw hidden bars thriving despite official bans, with gangsters and bootleggers playing central roles in the city’s underground economy.
Many bars focus on sustainability by using local ingredients for cocktails and minimizing waste to preserve Chicago's urban environment.
Chicago Prohibition Tours, featured on The Adventure Collective, offers guided Prohibition-era speakeasy experiences in Chicago, Illinois. The company runs two signature tours that explore the city's hidden bars and social history. The Hidden In Plain Sight (Downtown Walking Speakeasy Tour) is a 2.5-hour walking experience that traces Prohibition-era nightlife, examining contrasts between gangsters and high society and how class divisions shaped drinking culture. The Original Chicago Prohibition Tour is a 3.5-hour journey through four neighborhood speakeasies where guests visit multiple hidden bars, hear period stories, and sample signature drinks while keeping the freedom to order at their leisure. Guides provide historical context about Prohibition, organized crime, architecture, and social life, connecting archival anecdotes with modern landmarks. Tours balance storytelling with on-site visits, making the history accessible for visitors new to Chicago and for repeat attendees seeking deeper local insight. Routes emphasize responsible, licensed operations and partnership with participating venues to access authentic speakeasy spaces. Visitors can expect expert narration, curated routes, and opportunities to experience period-inspired cocktails in neighborhood bars. The tours are suitable for adults interested in history, architecture, and nightlife culture. Chicago Prohibition Tours focuses on immersive, factual interpretation of Prohibition-era topics without sensationalizing events, and maintains transparent tour descriptions, meeting locations, and durations to set clear expectations for guests. Tours operate in public spaces and licensed partner venues, and participants must be of legal drinking age to sample alcoholic beverages. Booking and reservation details, including meeting instructions and accessibility notes, are provided when booked to set clear expectations.
Book with Chicago Prohibition Tours