Hidden In Plain Sight (Downtown Walking Speakeasy Tour)
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Average fitness required; you should be comfortable walking for extended periods.
Overview
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.
Details
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.
Trail Tips
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.
Local Insights
Hidden Gems
- The Hidden Vault Bar - a speakeasy behind an unassuming door
- Underground Jazz Club with live performances
Wildlife
- Pigeons in the city squares
- Urban squirrels in parks
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.
Photography Tips
Best Times
Best Viewpoints
- Skyline from Millennium Park
- Street-level shots along State Street
What to Photograph
Recommended Gear
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 specific
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.