Walking Tour: Underground Chicago via the Pedway

If you’re visiting Chicago and want a different perspective on the city’s architecture and history, this Underground Chicago via the Pedway tour might be just what you’re looking for. While most travelers stick to the usual sights, this experience takes you beneath the streets, into the city’s lesser-known network of tunnels and walkways, alongside some of Chicago’s most famous landmarks.

What we really love about this tour is how it combines urban exploration with engaging storytelling — you get to see a side of Chicago that’s often hidden from travelers. Plus, the tour’s inclusion of public transit, like a ride on the Loop’s L train, makes it easy to navigate and quite affordable at $65 per person.

A potential consideration is that this tour involves walking and stairs, which might not be ideal if you have mobility issues or prefer more leisurely sightseeing. It’s generally suited for those who enjoy discovering unique city features and are comfortable on foot for about three hours.

If you’re a curious traveler who loves architecture, history, and discovering Chicago’s secret spaces, this tour could be a great fit. It also offers a more intimate, small-group experience—perfect if you prefer personalized insights over large tour buses.

Key Points

• Unique underground experience: Walk through Chicago’s Pedway, a network of underground tunnels and elevated walkways, rarely explored by travelers.
• Expert guidance: The tour is led by knowledgeable guides who bring the city’s architecture and history to life.
• Landmark stops: Visit iconic spots like the Tiffany Dome, Macy’s Walnut Room, Millennium Park, and the Art Institute lions.
• Includes public transit: Ride the L train through the Loop, offering a quick and easy way to see the city’s core.
• Walk at your own pace: Small groups ensure a personal experience, with enough flexibility to ask questions.
• Cost-effective: For $65, you get a comprehensive tour, transit fare, and expert insights.

A Detailed Look at the Experience

We’ll walk through each stop to give you a sense of what to expect — and why it might make your trip to Chicago more memorable.

Starting Point: Swissotel Chicago

The tour begins in the lobby of Swissotel Chicago, a central spot downtown. Meeting here means you’re already in the heart of the city’s vibrant Loop area. The guide greets you, and after a quick briefing, you descend into the Pedway. This initial part sets the tone for the tour: a seamless transition from the above-ground hustle to the underground world waiting below.

Chicago Pedway

The underground tunnel system itself is a treat. As you walk through this network, you’ll learn about its history and how it connects buildings, transit stations, and shopping centers. The fact that the walk involves going above and below ground multiple times keeps things dynamic. It’s fascinating to see how the Pedway serves as a hidden corridor for locals and visitors, especially in bad weather.

The reviews highlight how the guide’s storytelling makes this segment engaging. Sally_C mentions, “Going in and out of unnoticeable parts of buildings down to the pedway was a treat,” which captures the magical feeling of uncovering a secret city beneath the streets.

Chicago Cultural Center

Next up is the Chicago Cultural Center, home to the city’s famed Tiffany Dome. This is a highlight for many visitors because of its stunning architecture and beautiful stained glass. The guide points out details that casual visitors might miss, making it a visual feast. One review notes that the guide showed many art & architectural treats, which is exactly what makes this stop special.

Macy’s on State Street

Here, you’ll see the historic Macy’s building, originally Marshall Field’s. The architecture is impressive, and the Tiffany dome inside is worth the visit. Don’t miss the Walnut Room and “The Great Tree,” especially if you’re visiting during the holiday season. Many reviews rave about this stop, with one mentioning how the store’s holiday decorations and windows add to the experience.

Block 37 and Pedway Strolling

Continuing through the Pedway, you’ll pass through Block 37, a popular shopping mall connected to the underground network. It’s a lively spot, giving you a taste of Chicago’s bustling retail scene. The tour then ascends to Daley Bicentennial Plaza, where you’ll get a view of the iconic Picasso sculpture and visit the Christkindlmarket if it’s the season. The market’s atmosphere and festive spirit are often singled out as memorable.

City Hall and the Loop Ride

From there, you’ll see Chicago’s City Hall and the County Building, which often hosts wedding ceremonies in the Marriage Court — a fun little detail the guide might share. Afterward, you jump on the L train for a quick loop ride, giving you a different perspective of the city’s architecture from the inside of a subway car.

Route 66 & Millennium Park

The tour then visits the start and end point of Route 66, the legendary highway. Seeing the origin/terminus is a nostalgic moment for road trip fans, and the lions at the Art Institute add a touch of classic Chicago charm. Finally, the journey ends at Millennium Park with the famous Cloud Gate sculpture, “The Bean,” and the city’s Christmas tree during the holiday season. Many travelers say this is a fitting, iconic end to their Chicago adventure.

The Practical Side: What You Need to Know

Duration and Group Size: The tour lasts roughly three hours, which is a manageable length for most travelers. With only 10 people maximum, you get a more personal experience, and you’ll find it easier to ask questions and interact with the guide.

Price and Value: At $65, this tour offers great value considering it includes transit fare and access to multiple landmarks. The small-group format and knowledgeable guide make it a more immersive experience compared to self-guided wandering.

Mobility: Be prepared for some walking and stairs, as not all train stations are equipped with elevators. The physical effort is moderate; if you’re comfortable on your feet, you’ll enjoy the experience more.

Booking & Availability: It’s recommended to book about three weeks in advance, especially during peak seasons. The tour departs at 10:00 am from Swissotel Chicago.

Authentic Feedback from Participants

The high praise from past guests speaks volumes. Sally_C describes the tour as “SO fascinating,” especially the moments of entering hidden parts of buildings. Missi_G calls it a “hidden gem,” with her guide Tom’s passion shining through. Franci_R emphasizes the guide’s knowledge and willingness to accommodate needs, making it a highlight of her trip.

Many reviews mention how the guide’s storytelling and local knowledge bring the city’s architecture and history to life, making it more than just a walk through tunnels. The shared sentiment is that it’s a must-do for anyone wanting a more intimate and insightful glimpse into Chicago.

Who Will Love This Tour?

This experience suits curious travelers who enjoy architecture, history, and discovering off-the-beaten-path city features. If you like walking with a small group and having a guide who can tailor the experience to your interests, you’ll find this tour rewarding. It’s also ideal if you want to combine sightseeing with some practical transit experience — a perfect blend for those who appreciate efficient, yet immersive city explorations.

While not specifically designed for families with young children, older kids with a curiosity for urban adventures may find it equally engaging. Just keep in mind the walking and stairs involved.

FAQs

Is the tour suitable for people with mobility issues?
It involves walking and climbing stairs, so it might not be ideal for travelers with limited mobility.

Does the tour include transportation?
Yes, it includes transit tickets, specifically a ride on the Loop’s L train, which is part of the experience.

How long does the tour last?
Approximately three hours, giving you enough time to enjoy each stop without feeling rushed.

What is the group size?
A maximum of 10 travelers, ensuring a more intimate and personalized experience.

What should I wear?
Comfortable walking shoes are recommended since you’ll be walking and standing quite a bit.

Are the stops indoors or outdoors?
Most stops are indoors or in covered spaces, but some outdoor walking occurs, especially when ascending from the Pedway to view landmarks.

What’s included in the price?
Transit fare and a knowledgeable guide are included in the $65 ticket.

Can I cancel if my plans change?
Yes, the tour offers free cancellation up to 24 hours in advance for a full refund.

Is this tour family-friendly?
While not specifically marketed for children, older kids with curiosity about architecture and urban spaces might enjoy it.

When is the best time to take this tour?
The tour starts at 10:00 am, and morning tends to be less crowded. It’s available year-round, but check for seasonal activities like the Christkindlmarket if you visit during winter.

Final Thoughts

If you’re after a tour that mixes urban exploration with cultural and historic sights, this Underground Chicago via the Pedway experience stands out. It’s especially great for those who like to dig a little beneath the surface and appreciate the city’s architectural details up close. The small-group setting and passionate guides make it feel more like a friendly, personalized discovery rather than a scripted tour.

While it’s not the right choice if you prefer a leisurely, sit-down sightseeing day or have mobility concerns, for most travelers, this walk through Chicago’s underground passages offers a fresh perspective. It’s a clever way to see the city’s secrets, learn about its design, and end at the iconic Millennium Park—all in just a few hours.

Whether you’re a seasoned Chicago visitor looking for something different or a first-timer eager to uncover the city’s hidden stories, this tour deserves a spot on your itinerary.