THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Step into Chicago’s secret past with the Hidden In Plain Sight Downtown Walking Speakeasy Tour. Explore hidden bars, learn Prohibition stories, and experience the city’s clandestine nightlife history in a fun and engaging way.
Step into Chicago’s secret past with the Hidden In Plain Sight Downtown Walking Speakeasy Tour. Explore hidden bars, learn Prohibition stories, and experience the city’s clandestine nightlife history in a fun and engaging way.
Book with Chicago Prohibition Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Chicago Prohibition Tours · Chicago, Illinois
Discover Chicago’s lively history and secret side with the Hidden In Plain Sight Downtown Walking Speakeasy Tour offered by Chicago Prohibition Tours. This immersive experience takes you through the city’s historic downtown neighborhoods, uncovering hidden speakeasies, secret bars, and storytelling that brings Prohibition-era Chicago back to life. As you stroll through iconic streets, guides share fascinating tales of bootlegging, jazz, and the underground nightlife that once thrived behind unassuming storefronts. Ideal for history enthusiasts, cocktail lovers, and those seeking a unique city adventure, this tour combines walking, exploration, and cultural insight into a fun and memorable experience. Whether you're a first-time visitor or a local looking to rediscover Chicago’s vibrant past, this tour offers a behind-the-scenes look at the hidden gems that make Chicago’s nightlife legendary today.
moderate.
2–3 hours.
Average fitness required; you should be comfortable walking for extended periods.
Yes, the tour is family-friendly, but children should be able to walk for an extended period.
No, the tour provides historical insights and access to secret bars, but beverages are available for purchase at the venues.
Wear comfortable walking shoes and dress appropriately for the weather conditions on the day of your tour.
Most parts of the tour involve walking on sidewalks and may not be fully accessible for all mobility devices.
The tour includes several secret bar stops and historic sites, typically around 4-6 locations.
Yes, advance booking is recommended to secure your spot, especially during peak seasons.
Chicago’s Prohibition era witnessed a surge of clandestine bars, with many secret tunnels and hidden doors still intact today.
Efforts are ongoing to preserve historic underground structures and promote sustainable tourism practices downtown.
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