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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Average fitness required; you should be comfortable walking for extended periods.
Wildlife
History
Chicago’s Prohibition era witnessed a surge of clandestine bars, with many secret tunnels and hidden doors still intact today.
Conservation
Efforts are ongoing to preserve historic underground structures and promote sustainable tourism practices downtown.
Chicago Prohibition Tours
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.
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.
Location
Chicago, Illinois
Downtown and neighborhood meeting points
Tour Durations
2.5 & 3.5 hours
Short, immersive historical walks
Tours Offered
2 distinct tours
Different routes and speakeasy experiences
Focus
Prohibition history & cocktails
History, stories, and signature drinks
Secure tickets for the 2.5-hour downtown walking speakeasy tour or the 3.5-hour neighborhood speakeasy experience — limited group sizes for intimate, guided history tours.
Wear comfortable walking shoes
The tour covers multiple blocks, so comfortable footwear is recommended for an enjoyable experience.
Bring a portable charger
Keep your phone charged to capture photos and stay connected during the walking tour.
Check weather forecast
Dress appropriately for the weather, as parts of the tour are outdoors and involve walking in various conditions.
Arrive early
Meet your guide at the designated starting point to ensure a prompt start and full experience.
Comfortable walking shoes
Reliable shoes ensure comfort during the walking tour across downtown Chicago's streets.
Weather-appropriate clothing
Dress in layers or rain gear depending on the forecast to stay comfortable during outdoor segments.
spring|summer|fall|winter
Portable power bank
Keeps your devices charged to capture photos and access digital tour info.
Small backpack or bag
Use it to carry essentials like water, snacks, and personal items comfortably.