Discover Chicago’s Jazz Age and Art Deco Gems with a Guided Walking Tour
If you’re into architecture or history—and really, who isn’t?—this History of the Jazz Age at Chicago Art Deco Architecture Tour promises a stylish stroll through some of the city’s most striking buildings from the 1920s and 30s. We haven’t personally taken this tour, but based on the details, it looks like a solid option for anyone curious about Chicago’s architectural evolution and the vibrant era that shaped much of the city’s skyline.
What we like most? First, the small-group format makes for a more personal experience, and the knowledgeable guides seem to bring the buildings to life with stories you wouldn’t get just wandering on your own. Plus, the inclusion of interior access (or at least the opportunity to peek inside some buildings) adds a layer of richness to the experience. On the flip side, the tour’s duration of about 90 minutes might be a bit tight for those wanting a more leisurely exploration, especially if you’re a slow walker or want to linger at each stop. This tour looks especially suited for architecture buffs, history lovers, or anyone with a soft spot for vintage Chicago.
Key Points

- Focused on Art Deco Architecture: An in-depth look at Chicago’s iconic buildings from the 1920s and 30s.
- Guided Experience: Led by enthusiastic local guides who share stories and insights.
- Inside Access and Photo Opportunities: Includes stops at some buildings with interior views and great spots for photos.
- Short but Informative: About 1.5 hours, ideal for fitting into a busy day.
- Price and Value: $67 per person, which covers all fees, taxes, and the guide.
- Limited Group Size: Small-group tour, max 10 travelers, which helps keep it personal and engaging.
A Walk Through the Heart of Chicago’s Architectural Boom

This tour is a fantastic way to learn about Chicago’s roaring 20s and the rise of Art Deco skyscrapers. What makes it stand out is its ability to combine architecture with history, offering context about why these buildings look the way they do and what they represented during the Jazz Age.
You’ll start at 30 North LaSalle. Here, you’ll see a building that stands where the Chicago Stock Exchange once thrived and learn about its significance. It’s a quick stop, but a good way to set the scene and get your bearings. Walking past 30 N La Salle offers a glimpse into the city’s early skyscraper design, and your guide might share stories about how Chicago’s skyline evolved in this period.
The second stop is the Rookery Building, a true gem designed by Daniel Burnham and John Wellborn Root in 1888. You can step inside this historic building, which is considered Chicago’s oldest high-rise, and soak up its opulent exterior. Here, guides often highlight its blend of historic charm with modern updates, making it a favorite among architecture enthusiasts. Multiple reviewers appreciate the guide’s expertise, noting they “love the way the guide explained the architectural details.”
Next, the tour moves to the Field Building (also called La Salle National Bank Building), completed in 1934. This Art Deco marvel features distinct east and west entrances that rise dramatically, giving visitors a real sense of the style and grandeur of the period. Watching these details unfold helps you appreciate why Chicago’s skyline is so iconic.
The fourth stop is One North LaSalle, a building listed on the National Register of Historic Places. Built in 1930, it was the tallest structure in Chicago for 35 years. Many find this building reminiscent of the glamour of the Jazz Age, with its classic lines and historic significance. It’s a chance to feel connected to the city’s roaring 20s vibe, almost like stepping into a scene from The Great Gatsby.
The Chicago Board of Trade Building is next, a 45-story skyscraper that epitomizes Art Deco elegance. With its regal facade and historic role as a center of commerce, it’s often singled out as one of Chicago’s best examples of the style. Visitors frequently mention the building’s impressive exterior and the striking details that distinguish it from more modern glass boxes.
The tour concludes at the Chicago Architecture Center on Wacker Drive, which is more than just a final stop—it’s an invitation to continue exploring Chicago’s architecture on your own. The center often hosts exhibits and additional tours, making it a perfect resource if you want to extend your architectural journey.
Interested in history? Here are other past-focused experiences we've examined in Chicago
What You Can Expect from Each Stop

30 North LaSalle
This stop is ideal for those interested in the history of Chicago’s stock exchange and early skyscraper design. The exterior view is enough to spark curiosity, and your guide might share stories about the site’s evolution.
The Rookery Building
Stepping inside is a highlight, especially for architecture lovers. The building’s ornate lobby and historic significance make this a memorable part of the tour. It’s an opportunity to see how historic buildings have been preserved and adapted over time.
Field Building (La Salle National Bank)
A key Art Deco example, the building’s rising entrances offer a visual feast. Expect to learn about the style’s geometric and neo-archaic influences, as your guide points out details that are easy to overlook on your own.
One North LaSalle
This building’s history as a record-holder in the Chicago skyline makes it fascinating. Its interior and exterior details reflect the optimism and grandeur of the era, and it’s a great spot for photos.
Chicago Board of Trade Building
As one of the most iconic Art Deco skyscrapers, this building’s regal appearance and historical role make it a must-see. Many visitors comment on the detailed craftsmanship that’s still visible today.
Chicago Architecture Center
Here, you’ll get a broader perspective on Chicago’s architectural landscape, with exhibits and additional insights. It’s a good place to wind down and plan future explorations.
The Experience and Its Benefits
The small-group setting makes the tour more engaging, allowing you to ask questions and get personalized answers. Guides are described as enthusiastic and knowledgeable, helping you spot architectural details you might miss on your own. If you’re into photography, you’ll appreciate the curated spots for photos, especially the exteriors of the buildings.
The interior access (or at least the chance to peek inside) adds a special touch, making the experience more immersive. For those who love design details, the geometric shapes, decorations, and neo-archaic motifs typical of Art Deco will keep you captivated.
Pricing at $67 per person might seem a bit steep to some, but considering it covers all fees, taxes, and access to the Chicago Architecture Center, it’s a reasonable investment for an hour and a half of expert insights and memorable sights. It’s especially valuable for those wanting a structured, educational experience rather than wandering solo.
Practical Considerations

The tour lasts about 90 minutes, so it’s suitable for most travelers with moderate physical activity levels. Walking is the main activity, and while mostly straightforward, some stops involve brief interior visits, which may require passing through security or scheduling considerations. The group is kept to a maximum of 10 people, ensuring a more intimate experience but also means booking in advance is recommended.
It begins at 30 North LaSalle and finishes at the Chicago Board of Trade Building. Both locations are accessible via public transportation, and the tour is confirmed instantly after booking. It’s also flexible enough for most schedules, with free cancellation up to 24 hours beforehand.
Final Thoughts

If your interest lies in architecture, history, or both, this tour offers a well-rounded, engaging look at Chicago’s Art Deco skyscrapers and their stories. The guide’s enthusiasm and expertise seem to be a highlight, making complex details accessible and interesting. The combination of exterior views, interior glimpses, and historical context makes it a compelling way to spend a couple of hours in downtown Chicago.
While the tour is not overly long, it packs in enough detail and visual delight to satisfy most architecture aficionados. The price reflects the guided experience and access to the Chicago Architecture Center, making it a worthwhile purchase if you’re keen on learning about the city’s iconic buildings.
For those who enjoy walking tours, storytelling, and discovering architectural gems with a knowledgeable guide, this experience is likely to leave you with a greater appreciation for Chicago’s skyline and its jazz-age history.
History of the Jazz Age at Chicago Art Deco Architecture Tour
FAQs

Is this tour suitable for children?
While the tour is not explicitly targeted at children, it’s generally suitable for anyone with an interest in architecture and history. Children comfortable with walking and listening should be fine, but the focus on detailed stories might be more engaging for older kids or teens.
How long does the tour last?
The tour lasts approximately 1 hour and 30 minutes, making it a manageable activity for most travelers. It’s fast enough to fit into a busy sightseeing day but still detailed enough to feel rewarding.
Are interior visits included?
Yes, the tour includes opportunities to get inside some buildings, such as the Rookery Building and the Chicago Board of Trade. However, access may sometimes be subject to schedule changes or closures.
What’s the group size?
The tour limits participants to a maximum of 10 travelers, which helps keep it personal and allows the guide to answer questions comfortably.
Is this tour good for Instagram or photography?
Definitely. The stops include iconic exteriors and interiors perfect for photos. The guide will likely point out the best angles and photo spots.
What’s included in the price?
All fees and taxes are included, along with a professional local guide and access to the Chicago Architecture Center galleries. It’s a straightforward price for a well-organized experience.
Can I cancel or reschedule?
Yes, you can cancel for free up to 24 hours before the tour. Changes less than 24 hours out are not accepted, but the flexible cancellation policy offers peace of mind.
If you’re looking to combine architecture, history, and a taste of Chicago’s jazz-age glamour, this tour definitely deserves a spot on your itinerary. It’s a great way to learn, see, and appreciate the city’s iconic Art Deco skyline with an expert guide leading the way.
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