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.
Hidden In Plain Sight (Downtown Walking Speakeasy Tour)
3 hours • Ages 21+
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About This Adventure
Embark on a captivating 2.5-hour walking tour through Chicago's Prohibition era, uncovering the contrasting lives of gangsters and high society. Delve into the city's rich history, exploring class divisions and their impact on drinking culture, making this experience both enlightening and unforgettable.
Our downtown walking Prohibition experience
Duration
2 hours and 30 minutes
About
Explore Chicago’s Prohibition-era through the eyes of not just the gangsters but also high society. From "down and dirty" to "jackets required" explore both sides of Chicago's scofflaw lifestyle. Not only does this tour cover "the basics", we will dive into class divisions and how it affected their drinking.
Adventure 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
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.
Select participants and date
Adventure Hotspots in Chicago
Frequently Asked Questions
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.