Walking Tour: Underground Chicago via the Pedway

This walking tour through Chicago’s underground Pedway system offers a fresh perspective on the city, combining subterranean pathways with visits to celebrated landmarks. From the moment you meet your guide at the Swissotel, this experience promises a unique blend of history, architecture, and local charm—all within a manageable three-hour window.

What we love most about this tour is how it makes the city’s underground network accessible and engaging, revealing a seldom-seen part of Chicago’s urban fabric. The guides are praised for their wealth of knowledge and personable approach, making the tour both educational and fun. Plus, the seamless integration of public transit, including a ride on the Loop’s L train, adds a layer of convenience and authenticity.

One potential consideration is that the tour involves walking and some stairs, so it’s best suited for travelers with moderate fitness. Also, since it’s a small-group experience capped at 10 participants, it offers intimacy and plenty of personalized attention—perfect for those who like to explore with a keen eye and a curious mind.

This tour suits travelers who are interested in architecture, city history, or just want a different view of Chicago beyond its famous skyline. It’s ideal for those who enjoy walking tours that mix indoor and outdoor sights and appreciate a knowledgeable guide with local insights.

Key Points

• Combines underground Pedway exploration with top Chicago landmarks
• Guided tour with a small group for a more personal experience
• Includes transit tickets and a quick Loop train ride
• Focus on architecture, history, and hidden city secrets
• Suitable for travelers with moderate physical fitness
• Highly praised for knowledgeable guides and interesting stops

A Deep Dive into the Chicago Pedway Experience

Starting Point: Swissotel Chicago
The tour begins conveniently in the lobby of Swissotel, located at 323 W Wacker Dr. Meeting here is ideal since it’s close to major downtown attractions and public transit. From this point, your guide will lead you into the city’s underground Pedway system—a network of tunnels and walkways connecting buildings, shops, and transit hubs beneath the streets of downtown Chicago.

Walking the Pedway
The core of the experience is a walk through this secretive network that many Chicagoans pass daily without a second thought. The Pedway stretches several blocks, offering a climate-controlled, sheltered way to navigate the city. Your guide will point out architectural features, hidden art, and interesting tidbits about how this underground system came to be. The tour involves multiple transitions between underground tunnels and above-ground streets, giving you a sense of how the city’s layers interact.

Chicago Cultural Center & Tiffany Dome
Next, the tour visits the Chicago Cultural Center, home to the renowned Tiffany Dome, often called the largest Tiffany glass dome in the world. Here, you’ll get a close-up look at this stunning piece of craftsmanship, along with other decorative features. Many reviews highlight how this stop provides a “wow” moment—some describe the Tiffany Dome as “amazing” and a “must-see” architectural gem.

Macy’s on State Street & The Walnut Room
From there, it’s on to Macy’s, a historic department store with an artful façade and an impressive Tiffany dome inside. The Walnut Room, famous for its large Christmas tree, is a highlight for many visitors. The store isn’t just a shopping destination; it’s a piece of Chicago history. Your guide will share stories about its architecture and the significance of the windows, which are often beautifully decorated, especially during the holiday season.

Strolling Block 37 & Daley Bicentennial Plaza
The tour continues through Block 37, a popular shopping mall connected via the Pedway, giving a modern, vibrant contrast to the historic stops. Then, you’ll step out from underground at Daley Bicentennial Plaza to see the iconic Picasso sculpture and, if visiting during the right season, the Christkindlmarket, which many reviewers say is “the most authentic outside Europe.” It’s a lively, festive space that adds a touch of holiday spirit.

City Hall & Loop Transit
Next, you’ll see Chicago’s City Hall and County Building, iconic for their architecture and local governance. If you’re lucky, you might even witness a wedding at the Marriage Court—a fun detail many travelers enjoy. Then, a quick ride on the L train through the Loop introduces you to Chicago’s elevated transit system, which is both practical and historic.

Route 66 & Millennium Park
The tour’s final stops include the origin and terminus of Route 66, a nostalgic touchpoint for American road trip history. After that, the tour culminates at Millennium Park, where you’ll see Cloud Gate, or “The Bean,” a photo magnet. If visiting during the holiday season, you’ll also see the city’s Christmas tree and festive decorations.

What’s Included and What to Expect

This tour offers excellent value for $65 per person. It covers transit tickets and a guided walk, making it a cost-effective way to explore both the underground and above-ground parts of Chicago. The small group size, capped at 10 travelers, fosters an intimate atmosphere where questions are encouraged, and the guide can tailor the experience slightly based on interests.

Since the tour involves walking, standing, and stairs, it’s best suited for travelers with moderate physical fitness. The itinerary’s timing—about three hours—means you’ll see a lot without feeling rushed, and the inclusion of transit fare means you won’t need to worry about extra expenses.

The reviews are glowing about the guides, with many praising their knowledge, friendliness, and ability to personalize the experience. One reviewer called their guide “extremely knowledgeable and personable,” emphasizing the value of a local expert leading the way.

The Value in Details: Why This Tour Matters

What makes this tour stand out is its focus on Chicago’s lesser-known subterranean world paired with well-loved landmarks. Most visitors see downtown Chicago from street level, snapping photos of skyscrapers or visiting iconic spots like Millennium Park. But few realize the extensive underground walkway system that links many buildings and transit points—this tour offers a chance to uncover that hidden layer.

The architectural highlights, such as the Tiffany Dome and historic Macy’s, provide cultural context and visual delight. The art at Daley Bicentennial Plaza and the famous sculptures further enrich the experience, offering a mix of art, history, and urban life.

The inclusion of transit tickets and a Loop train ride adds an authentic Chicago touch, showing how residents move through the city daily. Reviewers note that guides often share extra tidbits about the city’s history and architecture, making the experience both fun and educational.

Who Will Love This Tour?

This experience is perfect for architecture enthusiasts, history buffs, or anyone curious about Chicago’s underground infrastructure. It’s especially suited for travelers who enjoy walking and exploring city neighborhoods intimately. If you’re traveling during the winter or rainy days, the Pedway offers a pleasant escape from the elements, making it a practical choice.

It’s also a great option for those who prefer a small, guided group over large bus tours, valuing personalized attention and the chance to ask questions.

Final Thoughts

In essence, this tour offers a wonderful blend of hidden city secrets and iconic landmarks. It’s a chance to see Chicago from a different angle—beneath the streets and above the city’s vibrant neighborhoods. The combination of underground tunnels, art, architecture, and lively cityscapes makes for an engaging, well-rounded experience.

If you’re looking for a value-packed, authentic glimpse of Chicago that’s both educational and fun, this tour should be on your list. The knowledgeable guides, stunning views, and unique access make it a memorable addition to any Chicago visit.

FAQ

Is this tour suitable for all fitness levels?
This tour involves walking, stairs, and some standing, so it’s best for travelers with moderate physical fitness. If you can walk comfortably for a few hours and handle stairs, you’ll be fine.

How long is the tour?
It lasts approximately three hours, covering a mix of underground and above-ground stops.

Are transit tickets included?
Yes, the tour includes transit fare and a quick ride through the Loop on the L train.

What is the group size?
The tour is capped at a maximum of 10 travelers, ensuring a more personalized experience.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is this tour good for holiday visits?
Absolutely. Stops like Daley Bicentennial Plaza and the Christkindlmarket are especially festive during the holiday season, adding extra charm to the experience.

To sum it up, this Underground Chicago Pedway Tour offers a rich, accessible look at the city’s hidden underground network and its most iconic sights. It’s a fantastic choice for travelers wanting a mix of art, architecture, and urban history, all with the guidance of friendly, knowledgeable locals. Whether you’re a first-timer or a seasoned visitor, it’s an experience that reveals Chicago’s layers—both literal and cultural—that most visitors never get to see.