Chicago Walk: Prohibition, Architecture & Hidden Gems

The Magnificent Mile, Chicago



Explore Chicago’s streets on foot and uncover the legacy of the Prohibition Era. See iconic sights, stunning architecture, and learn how history, crime, and design shaped the city we know today.

Chicago Prohibition and Architecture Walking Tour

This guided walking tour in downtown Chicago suits history and architecture enthusiasts interested in the city's Prohibition era and iconic landmarks.

Highlights

  • Walk the Pedway, Riverwalk, and visit Millennium Park and The Bean
  • Discover Chicago’s Prohibition past with expert local guides
  • See iconic architecture including the Wrigley Building and Tribune Tower
  • Enjoy a Chicago-style popcorn tasting
  • Private tour for a personalized experience

Description

Explore Chicago’s Prohibition Era and its impact on the city’s growth and architecture. Learn about landmark buildings that represent Chicago’s history and future.

Begin at the Chicago Theater, then walk along the Riverwalk to view Marina Towers, Willis Tower, and the Jewelers Building. Observe Art Deco architecture at the London House and DuSable Bridge.

Visit the Chicago Cultural Center to appreciate its design and enjoy a local Chicago-style popcorn tasting. Discover the history behind the Wrigley Building, Tribune Tower, and Chicago’s journalism roots.

The tour concludes at Millennium Park with The Bean sculpture, where your guide will share lunch suggestions and additional sights to visit.

Includes

  • Guided walking tour through downtown Chicago
  • Expert local English-speaking guide
  • Chicago-style popcorn tasting
  • Visit to Millennium Park and The Bean
  • Stops at Prohibition-era and architectural landmarks
  • Entry to the Chicago Pedway

Excludes

  • Gratuities

Important Information

  • This carbon-neutral tour is operated by a B Corp certified company committed to responsible travel.
  • Children under 6 join free; the tour is child-friendly.
  • The route covers 4.8 to 6.4 km (3–4 miles) and suits all fitness levels.
  • The tour runs rain, shine, or snow; dress accordingly.

Easy Cancellation

Cancel up to 24 hours in advance for a full refund.

Frequently Asked Questions

The tour explores Chicago’s Prohibition era, iconic architecture like the Wrigley Building and Tribune Tower, and features stops at Millennium Park, the Pedway, and the Riverwalk.
This guided walking tour takes place in downtown Chicago, covering key landmarks along the Chicago Riverwalk, Pedway, and Millennium Park areas.
Expert local guides with knowledge of Chicago’s Prohibition history and architecture lead the tour.
The tour is available throughout the year; check the booking website for current availability and hours.
Yes, the walking tour is family-friendly but best suited for those interested in history and architecture.
Yes, the tour includes a tasting of Chicago-style popcorn as part of the experience.
Tour durations can vary, so please check the official website for specific timing details.
Advance booking is recommended to secure your spot and enjoy a private, personalized experience.
Accessibility may vary by location; check the tour provider’s website for specific information about wheelchair access.
The tour highlights iconic buildings such as the Wrigley Building, Tribune Tower, and other notable Chicago Riverwalk structures.

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