Original Chicago Prohibition Tour: Discover Hidden Speakeasies
Difficulty
easy
Duration
3.5 hours
Fitness Level
Suitable for all fitness levels; involves moderate walking between stops over mostly flat urban terrain.
Overview
Explore Chicago’s secret speakeasies with a private guided tour that mixes history and signature drinks. Discover fascinating stories from the Prohibition era while tasting iconic cocktails across four hidden bars.
Details
Step back in time with the Original Chicago Prohibition Tour, a captivating 3.5-hour private food tour through four of Chicago’s best neighborhood speakeasies. Guided by an expert storyteller, you’ll experience the thrill of the Prohibition era, hearing intriguing stories about Chicago’s secret nightlife and notorious gangsters while sipping on the era’s signature cocktails. This immersive experience blends history, culture, and the excitement of discovering hidden bars where you have the freedom to order drinks at your own pace. Whether you're a history buff or a cocktail enthusiast, this tour offers a unique way to explore Chicago’s rich past in an intimate setting. The tour moves at a relaxed pace, allowing you to soak in each venue’s atmosphere and enjoy personalized attention from your guide. Ideal for groups of friends, couples, or anyone looking for a unique night out, the Original Chicago Prohibition Tour delivers an engaging and memorable adventure through the city’s underworld legends.
Adventure Tips
Bring a Valid ID
You must be 21 or older with a government-issued ID to participate and order drinks.
Wear Comfortable Shoes
This tour involves walking between venues within neighborhoods, so comfortable footwear is recommended.
Stay Hydrated
Enjoy water between tastings to stay hydrated throughout the 3.5-hour tour.
Arrive On Time
Tours start promptly and late arrivals may not be accommodated, so plan to arrive early.
Local Insights
Hidden Gems
- A small jazz club with a vintage vibe just off the main tour route
- An underground art gallery nearby that showcases speakeasy-inspired exhibits
Wildlife
- Urban squirrels
- Various city pigeons
History
Chicago's Prohibition era saw hidden bars thriving despite official bans, with gangsters and bootleggers playing central roles in the city’s underground economy.
Conservation
Many bars focus on sustainability by using local ingredients for cocktails and minimizing waste to preserve Chicago's urban environment.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- Outside the entrance of the first speakeasy with vintage signage
- City streets between stops showing historic architecture
- Dimly lit interior shots capturing bar ambiance
What to Photograph
Recommended Gear
Valid Photo ID
Required to prove legal drinking age at speakeasies.
Comfortable Walking Shoes
Necessary for walking between bar locations comfortably.
Light Jacket or Sweater
Helps stay warm during cooler evenings in fall.
fall specific
Compact Umbrella
Useful for unexpected rain showers during springtime.
spring specific