Walking Tour: Underground Chicago via the Pedway

Imagine wandering beneath the bustling streets of Chicago, where a network of underground tunnels known as the Pedway connects shops, offices, and landmarks, all with minimal exposure to the elements. For $65 per person, this 3-hour guided tour offers you a chance to explore this little-known part of the city that many locals pass by without a second thought. Led by knowledgeable guides like Tom—whose passion for Chicago’s architecture and history shines through—you’ll navigate the Chicago Pedway, visit iconic landmarks, and even hop on the Loop’s L train for a quick ride.

What we love most about this experience is how it combines urban exploration with cultural highlights, like the stunning Tiffany Dome at the Cultural Center and the historic roots of Route 66. Plus, the tour’s small-group format ensures a personal touch, making it easier to ask questions and get tailored insights. The inclusion of transit fare and a ride on the L train adds practical value, letting you experience Chicago’s transit system firsthand.

One thing to keep in mind is that this tour involves climbing stairs and navigating through some underground segments that aren’t fully accessible for everyone. It’s best suited for travelers with a moderate level of physical fitness who enjoy a mix of walking and urban sightseeing. Overall, whether you’re a history buff, an architecture lover, or simply curious about Chicago’s lesser-known corridors, this tour offers a unique perspective on the city.

Key Points

• Unique underground experience through Chicago’s Pedway system
• Visit key landmarks like the Cultural Center, Macy’s Walnut Room, and Millennium Park
• Engaging guides with deep local knowledge and storytelling skills
• Includes transit fare and a Loop train ride for practical city exploration
• Small-group setting enhances interaction and personalized attention
• Accessible for most physically able travelers but involves stairs

Discovering the Underground Chicago Pedway

Many visitors to Chicago are familiar with its stunning skyline, vibrant neighborhoods, and world-class museums. But how many realize that beneath the streets lies an extensive network of underground passageways connecting the Loop’s commercial core? This tour peels back the layers of the city’s hidden infrastructure, revealing a different side of Chicago’s urban fabric.

Why the Pedway Matters

The Pedway isn’t just a maze of tunnels; it’s a testament to Chicago’s practical approach to urban design, especially useful during winter months. Originally built to shield pedestrians from harsh weather, these corridors have become a cultural and architectural tapestry, lined with shops, art, and historic features. As one reviewer noted, “Going in and out of unnoticeable parts of buildings down to the pedway was a treat”—highlighting how surprising and fun it can be to uncover what’s hidden beneath your feet.

Starting Off: Swissotel Chicago

Your journey begins in the lobby of the Swissotel Chicago, situated at 323 W Wacker Drive. Meeting your guide here, you’ll descend into the Pedway—a step that instantly transports you from the busy street above into a quieter, more mysterious world. The initial walk takes about 15 minutes, giving you your first taste of the underground’s scale and design.

Walking the Chicago Pedway

The core of the tour is strolling through this network of tunnels and bridges that crisscross the city’s core. You’ll move several times between underground passages and above-ground streets, experiencing Chicago’s layered urban landscape firsthand. According to reviews, guides like Tom aren’t just knowledgeable about architecture—they’re passionate storytellers who make each stop engaging. One reviewer shared, “His storytelling was engaging, informative, and filled with Chicago’s hidden stories,” which makes all the difference in creating a memorable experience.

Architectural Highlights: The Tiffany Dome

A major highlight is the Chicago Cultural Center, home to one of the city’s most beautiful architectural features—the Tiffany Dome. This stunning stained glass masterpiece is a favorite among visitors, and seeing it up close offers a glimpse into Chicago’s decorative arts legacy. Visitors consistently praise the guide’s insights here, noting how they learned about the dome’s history and craftsmanship.

Macy’s on State Street

Next, the tour visits the iconic Macy’s building, which was originally Marshall Field’s. The architecture is impressive, especially the Tiffany dome inside, and you’ll get to see the Walnut Room’s Great Tree—a holiday tradition for many. Visitors have mentioned that “Marrying the historic architecture with modern retail makes Macy’s a must-see,” emphasizing the remarkable blend of old and new.

Strolling Through Block 37 and Daley Plaza

The walk through Block 37 adds a lively, contemporary shopping experience, while Daley Bicentennial Plaza offers a chance to step back outside and view the Picasso sculpture. Here, you’ll also visit the Christkindlmarket, a festive holiday market that many reviews describe as “the most authentic outside Europe,” perfect for holiday shopping or just soaking in Chicago’s winter spirit.

The Loop on the L Train

A quick, included ride on the L train takes you through the Loop, offering a true taste of Chicago’s transit system. The train ride, lasting around 15 minutes, is a practical and fun way to see the city’s core from a different perspective—an experience some reviews highlight as a small but meaningful part of the tour.

Route 66 and Millennium Park

The tour’s finale is a visit to Route 66’s starting point, where you’ll see the historic “Mother Road” sign, followed by a walk to Millennium Park. Here, the famous Cloud Gate sculpture—aka “The Bean”—becomes your photo backdrop. You’ll also see the city’s festive Christmas tree, a seasonal favorite according to many visitors.

Authentic Experiences and Honest Insights

What makes this tour stand out is not just the landmarks—but the stories and insights from guides like Tom. Visitors consistently mention how guides personalize the experience, sharing lesser-known facts and local tips. For example, one review notes, “He gave my son ideas for future explorations,” illustrating how this tour can connect you with authentic Chicago life beyond the surface.

Practical Details: Pricing, Duration, and Group Size

At $65, the tour offers good value considering the inclusion of transit tickets and a guided experience. The small-group size (maximum 10 travelers) means you’ll receive personalized attention, which is especially helpful when navigating busy urban areas. The 3-hour length strikes a balance—long enough to see many highlights without feeling rushed. The tour starts at 10 am, a perfect time to explore before the city gets too busy.

Accessibility and Considerations

While the tour involves stairs and walking, reviews suggest that most fit travelers will find it manageable. The tour’s physical demands are moderate, but it’s worth noting that not all train stations are equipped with elevators. If mobility is a concern, it’s best to inquire beforehand.

Why It’s Worth Your Time

If you’re interested in Chicago’s architecture, enjoy city history, or want a behind-the-scenes look at areas many visitors overlook, this tour offers a wealth of insights. The combination of underground passages and above-ground landmarks provides a layered experience that’s both fun and educational. Plus, the positive reviews underscore how guides like Tom make the experience engaging and memorable.

Who Will Love This Tour?

This experience is perfect for travelers who appreciate local stories and hidden corners, not just the typical tourist spots. It’s well-suited for those who enjoy walking and discovering new aspects of familiar cities. History buffs, architecture lovers, and curious explorers alike will find plenty to enjoy. Families with moderate fitness levels will appreciate the manageable pace and variety of sights.

Final Thoughts

The Underground Chicago Pedway Tour offers a charming, insightful look into a lesser-known side of the Windy City. You’ll love the way it combines urban exploration with visits to some of Chicago’s most iconic landmarks, all wrapped in a small-group setting that encourages interaction. The inclusion of transit and a train ride makes it practical and fun, offering a comprehensive city experience in just a few hours.

While it’s not suited for travelers with mobility concerns or those seeking an intense workout, it’s ideal for anyone wanting a personalized, authentic glimpse of Chicago’s layered cityscape. Whether you’re a first-time visitor or a seasoned local, this tour unlocks hidden stories and secret corridors that add depth and dimension to your city adventure.

FAQ

How long is the tour?
The tour lasts approximately 3 hours, giving you enough time to see key sites without feeling rushed.

What’s included in the price?
The price covers the guided tour, transit tickets, and a ride on the Loop’s L train, making the experience both convenient and cost-effective.

Where does the tour start and end?
It begins at the Swissotel Chicago and concludes at Millennium Park’s Cloud Gate, or “The Bean,” providing a scenic and central finish.

Is this tour suitable for children or seniors?
Most physically able travelers will enjoy it, but it involves stairs and walking. It’s best suited for those with moderate fitness levels.

Do I need to book in advance?
Yes, with an average booking window of 21 days, securing your spot in advance is recommended.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the start time.

How many people are on the tour?
The tour is limited to a maximum of 10 travelers, ensuring personalized attention.

Are meals or drinks included?
No, food and beverages are not included, so plan to bring snacks if needed.

Is the tour accessible for people with mobility issues?
Not all stations are equipped with elevators, and stairs are involved, so it may not be suitable for everyone with mobility challenges.

This guided walk through Chicago’s underground corridors and landmarks offers a balanced mix of history, architecture, and local color—perfect for curious travelers eager to see the city from a different angle. With knowledgeable guides like Tom leading the way, you’ll gain a richer understanding of Chicago’s layered urban story.