Chicago Prohibition Tours: Walk Chicago’s Hidden History
Difficulty
easy
Duration
2–3 hours
Fitness Level
Participants should be able to walk several city blocks on flat, paved surfaces and stand during stops.
Overview
Step into Chicago’s Prohibition-era secrets with tours that weave history, hidden bars, and spirited storytelling through the city’s heart. Discover the ‘Old Chicago’ underground on foot or by bus with guides who bring the Roaring Twenties vividly to life.
Chicago Prohibition Tours: Walk Chicago’s Hidden History
Adventure Tips
Wear comfortable shoes
The walking tour covers several city blocks on paved surfaces; sturdy footwear ensures comfort throughout.
Plan for food and drink options
Many stops offer unique cocktails and food pairings—budget extra time and money to enjoy these local flavors.
Arrive early for check-in
Tours depart promptly from designated Chicago downtown locations; arriving 10-15 minutes early is recommended.
Bring ID for age verification
Since some stops include alcoholic beverages, participants must be 21+ with valid identification.
Local Insights
Wildlife
- Common city birds like pigeons and sparrows frequent downtown alleys
- Urban squirrels active in plazas and green spaces along the route
History
Chicago's Prohibition era was marked by notorious gangsters, bootlegging, and secret bars, which significantly shaped the city's culture and urban landscape.
Conservation
Chicago Prohibition Tours emphasizes supporting local historic venues and promotes responsible tourism that respects downtown’s architecture and community.
Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Ensures ease and stability during the urban walking segments.
Light rain jacket
Protects against unpredictable Chicago showers during cooler months.
spring|fall specific
Photo-friendly smartphone or camera
Captures unique architecture and hidden speakeasy interiors along the route.
Valid government-issued ID
Required for age verification at stops serving alcohol.