Adventure Collective
null - Chicago

Hidden In Plain Sight (Downtown Walking Speakeasy Tour)

Chicagomoderate

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.

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.

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Reliable shoes ensure comfort during the walking tour across downtown Chicago's streets.

Weather-appropriate clothing

Essential

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.

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