Chicago Walking Tour: Art Deco Skyscrapers Riverfront

When it comes to Chicago, architecture isn’t just a backdrop—it’s a defining feature. This small-group walking tour offers a rare chance to peek inside five of the city’s most iconic Art Deco skyscrapers, revealing details most visitors miss. For those with a penchant for design or history buffs eager to understand the city’s structural character, this tour promises a focused, personal experience.

Two things we particularly love about this experience? First, the expert narration that transforms cold stone and glass into stories of Chicago’s ambitions and innovations. Second, the opportunity to go inside buildings, including lobbies and interiors, which adds a layer of authenticity and intimacy to viewing the skyline.

A possible consideration? The tour is quite brief—about 90 minutes—so those wanting a more comprehensive architectural journey might need to supplement it with other explorations. Still, for its size and focus, it offers one of the best value insights into Chicago’s Art Deco heritage.

If you’re the type to stop and admire building details, enjoy learning from passionate guides, and prefer walking through compact, less crowded spaces, this tour suits you perfectly. It’s especially ideal for travelers who appreciate architecture, history, or simply want a richer understanding of Chicago’s skyline beyond the usual postcard shots.

Key Points

• Small-group size ensures personalized attention and easier interaction with guides.
• Focuses on five prominent Art Deco skyscrapers along Chicago’s riverfront.
• Includes interior access to notable buildings, providing a behind-the-scenes look.
• Guided by certified, knowledgeable experts passionate about Chicago architecture.
• Walks are easy and accessible, making it suitable for most travelers.
• Offers value for money with included access to the Chicago Architecture Center galleries.

Why This Tour Is a Must-Do for Architecture Enthusiasts

Chicago’s skyline is a testament to its innovative spirit, especially during the roaring 20s when Art Deco architecture flourished. This tour zeroes in on that era, giving you a detailed glance at the craftsmanship and style that defined skyscrapers more than a century ago. What makes this experience special is the combination of exterior views and interior explorations, something that elevates it from a simple sightseeing walk to an educational journey.

You’ll meet your guide at the Chicago Architecture Center, an excellent starting point for any architecture lover. From there, the tour moves along the riverfront, where many of the city’s most celebrated buildings proudly display their geometric patterns, ornate details, and distinctive setbacks. These structures, such as the Carbide and Carbon Building, are more than just tall buildings—they’re symbols of Chicago’s bold ambitions and architectural evolution.

Starting at the Chicago River

The tour kicks off here, with the riverfront as your visual anchor. Your guide discusses buildings built in the Art Deco style, giving you context about why this period was so crucial for Chicago’s skyline. Expect to learn how the design reflected the optimism and modernity of the 1920s, with geometric shapes, stepped forms, and decorative motifs.

Exterior Views of Notable Skyscrapers

The next stops include stunning facades: the Crumbl Cream building, the Carbide and Carbon Building, the 66 E Wacker Place (the former Chicago Motor Club Building), and the Trustees System Service Building at 182 W Lake St. Each has distinct features; for example, the Carbide and Carbon Building is notable for its green terracotta exterior and gold accents, while the Wacker Place building is renowned for its historic lobby.

Most reviews highlight how much more engaging it is to see these buildings with expert commentary. One reviewer praised their guide’s extensive knowledge and engaging storytelling, calling the tour “outstanding” and a highlight of their trip. Another mentioned how the guides often have inside connections, which provide “great inside scoops” on the interior spaces.

Inside the Buildings

The tour’s real value lies in interior access—a feature rarely offered in walking tours. You’ll get a chance to see the interiors of some buildings, which can dramatically change how you perceive their exteriors. The guide explains stylistic elements and building histories, making it easier to appreciate the craftsmanship and design choices.

Visiting Merchandise Mart

The final stop, the Merchandise Mart, is one of Chicago’s architectural giants. Though the tour only allows exterior visits, the building’s grandeur makes it worth the short stop. Its size alone encapsulates the ambition of Chicago’s commercial architecture.

The Experience: What to Expect

This 1 hour 30-minute tour is perfectly paced for those who prefer quality over quantity. The small group (max 15) means you won’t feel lost in a crowd, and questions are encouraged. You should plan for comfortable walking shoes because most of the tour is on foot, although it’s easy to stop and enjoy the views.

The tour includes admission to the Chicago Architecture Center galleries, which is a wonderful bonus. It allows you to further explore Chicago’s architectural history at your own pace afterward. The narration is delivered by a professional, certified guide who’s passionate about sharing their expertise, making the experience both informative and fun.

Cost and Value

At $35 per person, the tour offers excellent value. For this price, you get a quality guided experience, interior views of historic buildings, and access to the galleries—an affordable way to deepen your understanding of Chicago’s architectural prowess. Many reviewers mention how guides’ deep knowledge and engaging stories make the experience well worth the fee.

Practical Considerations

The tour departs from the Chicago Architecture Center, conveniently located near public transportation. It’s accessible to most travelers, with no specific restrictions mentioned, and service animals are welcome. Keep in mind, interior access is subject to change depending on building schedules, especially during weekends or holidays.

Who Should Book This Tour?

This experience is ideal for architecture lovers, history buffs, or anyone curious about Chicago’s skyline. It’s perfect for visitors who want a personalized, insider view of historic buildings without feeling rushed or overwhelmed. Because of its manageable length, it suits those with limited time but a keen interest in design and urban history.

The Sum Up: Why You Should Consider This Tour

This small-group walking tour offers a compelling mix of expert narration, interior access, and iconic architecture—all for a reasonable price. It elevates a typical sightseeing walk into a meaningful exploration of Chicago’s Art Deco period, revealing details most visitors overlook.

The tour’s strength lies in the passionate guides and the opportunity to see inside buildings—features that create a richer, more personal experience. Whether you’re a dedicated architecture enthusiast or simply someone who appreciates beautifully designed spaces, this tour will deepen your appreciation for Chicago’s skyline.

Most travelers will find it well worth the investment for its blend of education, accessibility, and authentic architecture. If you’re eager to learn about Chicago’s architectural story from those who know it best, this tour provides a memorable, insightful glimpse into the city’s design legacy.

FAQs

How long is the tour?
The tour lasts approximately 1 hour 30 minutes, making it a manageable addition to your day without feeling rushed.

What buildings will we see?
You’ll view five notable Art Deco skyscrapers along the riverfront, including the Carbide and Carbon Building, the Chicago Motor Club Building, and the Trustees System Service Building.

Does the tour include interior visits?
Yes, the tour offers access to certain building interiors, including lobbies, which adds a special layer of authenticity.

Where does the tour start and end?
It begins at the Chicago Architecture Center at 111 E Wacker Dr and concludes near the Merchandise Mart at 222 W Merchandise Mart Plaza.

What is included in the price?
Your ticket covers the guided tour and access to the Chicago Architecture Center galleries. No additional fees are required for the buildings’ exteriors or interiors.

Is there a group size limit?
Yes, the tour is limited to a maximum of 15 travelers, ensuring a more intimate experience.

This tour stands out for its focus, affordability, and the chance to go inside Chicago’s landmark Art Deco buildings. Whether your interest is architectural or historical, it’s a smart choice for a memorable Chicago experience.