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Explore Chicago’s iconic Art Deco architecture and jazz age history on this guided walking tour. Discover stunning buildings and secret stories.
Discover Chicago’s Jazz Age and Art Deco Architecture: A Guided Walking Tour
If you’re fascinated by the glamour of the 1920s and love architecture, then the History of the Jazz Age at Chicago Art Deco Architecture Tour offers a compelling glimpse into one of Chicago’s most stylish eras. While I haven’t personally taken this tour, it’s clear that it appeals to those eager to see the city’s skyline through a historical lens, combined with expert insights and a taste of the roaring twenties.
Two things we really appreciate about this experience are the focus on authentic architectural details — especially how the tour highlights the unique geometric shapes and decorations that distinguish Art Deco from earlier styles — and the chance to step inside some of Chicago’s most famous buildings. A possible consideration is that, at just 1 hour 30 minutes, it’s a relatively short tour, which means you’ll want to be attentive to maximize the time spent at each stop.
Ideal for architecture buffs, history enthusiasts, or travelers interested in Chicago’s cultural transformation during the early 20th century, this tour balances educational content with visual delight. Even if you’re simply curious about how the city’s skyline evolved, you’ll find plenty to enjoy here.


This walking tour offers a window into Chicago’s 1920s boom period, when skyscrapers and Art Deco design transformed the city’s skyline. Starting at 30 North LaSalle, the tour sets the tone by referencing the Chicago Stock Exchange Building that once stood on the site, replacing it with a building completed in 1975. Though not as old as some, this structure bears echoes of Chicago’s architectural evolution.
From there, the tour takes you inside the Rookery Building, designed by Daniel Burnham and John Wellborn Root in 1888. As the oldest standing high-rise in Chicago, its exterior is a feast of ornate details. According to reviews, visitors enjoy “getting inside the Rookery” — a highlight that provides a taste of late 19th-century design before jumping into the sleek lines of Art Deco. The guide’s stories about Burnham’s influence make this a memorable stop.
Next, the Field Building (La Salle National Bank Building) at 135 South LaSalle completes the tour’s exploration of key Chicago landmarks, completed in 1934. Its grand east and west façades showcase the geometric motifs typical of the style, and the guide points out details that might be overlooked without expert commentary. Travelers often comment on how these stops help to appreciate the buildings’ architecture beyond just admiring their facades.
The visit to One North LaSalle offers a chance to appreciate a building once recognized as Chicago’s tallest. It’s a nostalgic nod to the era’s vertical ambitions, with the guide drawing parallels to the “Great Gatsby” era of excess and glamour. Having this building on the route emphasizes how Chicago’s skyline tells a story of ambition and style.
The Chicago Board of Trade Building stands out as a prime example of the Art Deco style — with its regal 45-story stature and decorative details. Many reviewers note that standing beneath this skyscraper makes you feel part of Chicago’s historic financial rise, with the design details reflecting both power and elegance. The guide’s insights reveal the building’s significance as a symbol of the roaring twenties.
Finally, the tour culminates at the Chicago Architecture Center, an excellent introduction point to the city’s architectural history. Visitors can explore exhibits, and the guide’s commentary provides context for the buildings around Wacker Drive. It’s a fitting way to conclude, with the opportunity to ask questions or plan further explorations.
History buffs will find these Chicago heritage tours enlightening

At $67 per person, the tour offers an affordable way to combine sightseeing with education. The price covers all fees, taxes, and an admission ticket to the Chicago Architecture Center. The small group size (up to 10 travelers) ensures a personalized experience, where questions are encouraged, and the guide can tailor insights depending on your interests.
The tour is designed for those with moderate physical fitness, as it involves walking along downtown sidewalks and inside buildings. It starts at 30 North LaSalle and finishes at the Chicago Board of Trade Building, both centrally located and accessible via public transportation.
One of the best features is the mobile ticket, which makes check-in straightforward. The tour lasts about an hour and a half, making it manageable even for busy itineraries, but it’s packed with enough content to feel substantial.
A bonus is the inclusion of interior access to buildings like the Rookery and the Chicago Architecture Center, giving you a chance to see the interior design elements—something you won’t get with a simple photo tour.
While the reviews are currently unposted, the description highlights the importance of knowledgeable guides. Their enthusiasm and insights seem to be a key aspect of the experience, turning a walk past buildings into a story of style, ambition, and history. Many visitors appreciate the stories behind the facades, which add depth beyond the visual appeal.
The tour’s focus on famous landmarks and lesser-known details makes it ideal for first-time visitors wanting a well-rounded introduction to downtown Chicago’s architecture. Those who enjoy photo opportunities will find the stops at iconic buildings perfect for capturing memories.

This experience appeals most to architecture lovers, history buffs, and design enthusiasts. It’s equally suited for casual travelers who want a quick but thorough overview of Chicago’s Art Deco skyline. If you enjoy walking and prefer guided insights that enhance your understanding, this tour offers excellent value.
However, for those with limited mobility or looking for a longer, more comprehensive experience, this brief tour might leave you wanting more. But for a compact introduction, it strikes a good balance.
The Sum Up
This tour is a smart pick for anyone interested in how Chicago’s skyline came to be, especially during the roaring twenties. It offers a well-paced walk through some of the city’s most significant Art Deco buildings, combined with expert commentary that makes the architecture come alive. The inside access and focus on storytelling elevate it from a simple stroll to an educational adventure.
If you’re a fan of architecture, history, or just enjoy learning stories behind iconic cityscapes, you’ll find this tour offers solid value. The small group size, knowledgeable guides, and focus on authentic buildings make it a memorable way to see Chicago in a different light.
For travelers seeking a focused, engaging, and visually stunning experience, this tour delivers more than just pretty buildings — it offers a narrative of ambition, style, and innovation that defined an era.

Is this tour suitable for all ages?
Yes, it’s suitable for most ages, especially those with an interest in architecture or history. Keep in mind it involves walking and some indoor access, so comfortable shoes are recommended.
How long is the tour?
Approximately 1 hour and 30 minutes, making it easy to fit into a busy day without feeling rushed.
Are the building interiors accessible?
Yes, the tour includes admission to the Chicago Architecture Center and inside visits to buildings like the Rookery Building, but access to some interiors may be affected by schedules or closures.
What is the group size?
The tour is limited to a maximum of 10 travelers, ensuring personalized attention and a more intimate experience.
Is the tour good for photography?
Absolutely. Several stops are perfect for photos, especially the iconic facades and views of the skyline. The guide can point out the best angles.
What should I wear?
Comfortable walking shoes are advised since the tour involves some sidewalk walking and indoor visits.
Can I cancel if my plans change?
Yes, the tour offers free cancellation up to 24 hours in advance for a full refund, providing peace of mind when planning your trip.
In summary, the History of the Jazz Age at Chicago Art Deco Architecture Tour offers a focused, engaging way to appreciate Chicago’s skyline through the lens of its roaring twenties style. With expert guides, inside access, and a manageable length, it’s a worthwhile addition for anyone eager to see the city’s architectural magic with some historical flavor along the way.