Chicago Prohibition Tours: Walking Speakeasy History in Illinois
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; mainly walking on mixed urban surfaces with moderate pacing.
Overview
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: Walking Speakeasy History in Illinois
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Adventure Tips
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.
Local Insights
Wildlife
- Peregrine falcons nesting on skyscrapers
- Urban red tail hawks often spotted circling near the river
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.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
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 specific
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 specific