Step into Chicago’s hidden Prohibition-era past with Chicago Prohibition Tours. Discover secret speakeasies, gangster haunts, and historic pubs on a lively guided walk through downtown’s underground nightlife legacy.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; mainly walking on mixed urban surfaces with moderate pacing.
Wildlife
History
Chicago’s Prohibition era was marked by notorious gangsters like Al Capone, with speakeasies operating beneath the city’s surface—many of which the tours highlight.
Conservation
Tours promote responsible tourism by partnering with local businesses and encouraging minimal environmental impact downtown.
Chicago Prohibition Tours
Step into Chicago’s hidden Prohibition-era past with Chicago Prohibition Tours. Discover secret speakeasies, gangster haunts, and historic pubs on a lively guided walk through downtown’s underground nightlife legacy.
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 Shoes
The walking tours cover multiple city blocks on varied pavement; sturdy, supportive footwear makes the experience smoother.
Bring a Light Jacket
Downtown Chicago’s weather can shift quickly; a light jacket helps if your tour runs into cooler evenings.
Hydrate Ahead of Time
Though some stops feature drinks, water may not be available on the route; prepare accordingly.
Arrive Early
Tours often start near popular venues; arriving early guarantees a stress-free check-in and good seating.
Comfortable Walking Shoes
Provides necessary support for pavement and city terrain throughout the tour.
Light Jacket or Layer
Helps manage chilly or windy urban conditions.
spring|fall|winter
Portable Phone Charger
Allows you to stay connected and capture photos without worrying about battery drain.
Reusable Water Bottle
Keeps you hydrated during warmer months when water stops may be limited.
summer|spring