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Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop

Chicagoeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for most fitness levels; moderate walking involved

Overview

Uncover Chicago’s hidden underground tunnels and secret spots on this captivating walking tour. Perfect for history lovers and urban explorers, it reveals the city’s lesser-known sides that add depth to your visit. Ready to see Chicago in a whole new way?

Details

Discover Chicago like never before with the 'Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop' walking tour by Inside Chicago Walking Tours. This immersive experience takes you beneath the city's bustling streets, revealing an intricate network of underground tunnels, hidden passageways, and fascinating secret spots that most visitors never see. As you stroll through the pedestrian-friendly Pedway system, you’ll learn about its history, purpose, and the quirky stories behind these underground corridors connecting malls, offices, and transit hubs. The tour also uncovers lesser-known architectural gems and historic sites scattered throughout downtown Chicago, making it a perfect adventure for history buffs and curious explorers alike. You'll see iconic landmarks from a fresh perspective while discovering cozy cafes, secret entrances, and artistic murals hidden away from the crowds. Whether you're a first-time visitor or a seasoned local, this journey provides new insights into the city’s development and urban design. Comfortable walking shoes are recommended, as you'll spend approximately 2-3 hours exploring the city’s underground and street-level secrets. Make sure to bring your sense of curiosity and a camera to capture some of Chicago’s best-kept secrets. This tour is ideal year-round, offering a unique way to explore the city, whatever the season. Get ready to open your eyes and see Chicago through a different lens!

Trail Tips

Wear comfortable walking shoes

You'll be exploring both underground tunnels and street-level streets, so comfortable shoes are essential.

Bring a camera

Capture the unique architecture, murals, and secret passageways that make this tour special.

Check the weather forecast

While much of the tour is indoors, some segments are outdoor, so be prepared for rain or shine.

Arrive early

Getting to the meeting point a few minutes early ensures you don’t miss any part of the tour.

Local Insights

Hidden Gems

  • The historic 1893 Chicago Post Office lobby
  • An underground art installation hidden within the Pedway

Wildlife

  • Pigeons
  • City squirrels

History

The Chicago Pedway system was developed in the 1950s to connect buildings and provide safe passage for pedestrians during harsh weather conditions, shaping the city’s underground urban experience.

Conservation

The tour emphasizes sustainable urban exploration by highlighting eco-friendly building designs and encouraging respect for the city’s historic sites.

Photography Tips

Best Times

Golden hour
Midday for clear lighting

Best Viewpoints

  • The skybridge connection at State and Clark
  • Inside the Macy's building rooftop terrace

What to Photograph

Architectural details
Murals and street art
Cityscapes from indoor viewpoints

Recommended Gear

Comfortable walking shoes

Essential

You'll be walking for a couple of hours through indoor and outdoor parts of Chicago, so supportive shoes are a must.

Light rain jacket or umbrella

Be prepared for possible weather changes, especially during spring and fall.

spring|summer|fall|winter specific

Camera or smartphone

Capture the hidden murals, architecture, and unique passageways along the route.

Water bottle

Stay hydrated during your walk, especially on warm days.

Frequently Asked Questions

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