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Discover Chicago's Art Deco masterpieces inside historic buildings on this 2-hour walking tour for $35, with expert guides revealing secrets of the Roaring '20s.
Exploring Chicago’s Art Deco architecture takes on a new dimension with the Chicago Walking Tour: See Inside Art Deco Masterpieces. For just $35 per person, this 2-hour guided walk offers a rare opportunity to step inside some of the city’s most stunning buildings, most of which are usually closed to the public. The tour begins at 425 S. Financial Place, where the guide greets visitors next to a horse sculpture, ready to share stories and secrets of the 1920s era.
What makes this tour particularly appealing is the special interior access, allowing participants to see Art Deco interiors that most visitors only glimpse from the outside or from boat tours. The expert local guide leads the way through downtown Chicago, emphasizing the glamorous, glamorous, and glamorous style of the Roaring ’20s, along with the cultural backdrop of jazz, speakeasies, gangsters, and flappers.


This tour offers a rare chance to step inside several Chicago buildings showcasing Art Deco architecture. Unlike typical sightseeing tours, which only admire exteriors, this experience grants special access to interiors that are usually closed to the public. These spaces exemplify the gleaming materials and precise details that define the style, making it a feast for the eyes.
Participants will see interior spaces that evoke the Gatsby era, with interiors that radiate glitz, glamour, and elegance. The guide provides context, explaining not just the visual elements, but also the fascinating stories behind the buildings’ design and their role in the city’s history. This focus on interior architecture truly sets this tour apart from other Chicago architecture experiences.
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The tour focuses on buildings in the Loop and near the Chicago River, giving a comprehensive look at the most prominent Art Deco landmarks. Some of these buildings are familiar sights from boat tours, but the interiors are seldom accessible. This makes the tour perfect for those who wish to see hidden details and learn what makes these buildings special from the inside.
Participants walk through several carefully chosen interiors, each illustrating the futuristic style of Art Deco, which was designed to evoke progress and innovation. The glitz and precision of each site vividly demonstrate why this style became a symbol of the 1920s optimism—just before the 1929 Crash.

The typical 2-hour duration involves about 1.5 miles of walking, making it suitable for most fitness levels. The tour usually starts in the morning, providing a fresh perspective on Chicago’s architecture. Weather is not a concern, as the tour takes place rain or shine.
Participants will learn interesting stories about Chicago’s Roaring ’20s, including the era’s social scene, gangsters, jazz culture, and speakeasies. The guide’s storytelling brings the buildings’ history and design to life, making the experience both educational and entertaining.

What makes Inside Chicago Walking Tours stand out is their ability to combine architectural insight with insider access. This particular tour is their newest addition, highlighting Art Deco gems that are rarely seen from the inside. The small group size allows for a more personal experience, with plenty of opportunity to ask questions and get detailed explanations.
The guide’s expertise is frequently praised, with reviews emphasizing their knowledge, passion, and personability. It’s clear that guides like Henry and Silvia make this experience memorable through their engaging storytelling.
More Great Tours NearbyThe tour departs outdoors at 425 S. Financial Place, which is easily accessible and marked by the guide holding a binder. Booking options include free cancellation up to 24 hours in advance, offering flexibility for changing plans.
Participants should be prepared to be on their feet for 2 hours, with comfortable shoes recommended. The tour is conducted in English and is suitable for anyone interested in architecture, history, or the glamour of the 1920s.
At $35, this tour offers excellent value, especially considering the exclusive interior access in buildings that typically don’t allow entry. The small group size and expert guides ensure a high-quality, personalized experience. The 4.9-star rating from 7 reviews reflects widespread satisfaction, with particular praise for the knowledgeable guides and stunning interiors.
While the tour does not mention food or drinks, the visual and historical richness more than compensates. It is especially suited for those who appreciate architecture and history, and who want to see Chicago through a fascinating 1920s lens.
This walking tour brings the 1920s vividly to life, with interior access that reveals the futuristic elegance of Chicago’s Art Deco buildings. The tour’s expert guides make the history engaging, sharing stories of gangsters, jazz, and speakeasies that defined the era.
The 2-hour journey combines architecture, storytelling, and exclusive access, making it ideal for those who want more than just exterior views. It’s a cost-effective, informative, and entertaining way to explore Chicago’s architectural heritage.

Is this tour suitable for all weather conditions?
Yes, the tour takes place rain or shine, so dress accordingly for the weather.
How much walking is involved?
The walk covers approximately 1.5 miles over 2 hours, suitable for most fitness levels.
Are interior spaces truly off-limits to the public normally?
Yes, the tour provides special access to interiors that are usually not open to the general public.
What makes this tour different from a standard architecture cruise?
Unlike boat tours, this experience goes inside buildings, offering a closer look at the interiors and details often missed from outside.
What can I expect to learn about the 1920s?
The guide shares stories about the era’s social scene, gangsters, jazz age, and the futuristic design of Art Deco architecture.
How long is the tour?
The 2-hour tour covers several buildings in downtown Chicago.
Is there parking nearby?
While not specified, the meeting point at 425 S. Financial Place is centrally located downtown, with various parking options nearby.
Can I cancel if my plans change?
Yes, full refund is available if canceled up to 24 hours in advance.
What languages are the guides available in?
The tour is conducted in English only.
Who should consider taking this tour?
Anyone interested in architecture, history, or the glamour of the 1920s will find this tour especially rewarding.
This inside look at Chicago’s Art Deco buildings combines architecture, history, and exclusive interior access, making it a uniquely enriching experience for history buffs, architecture enthusiasts, and culture seekers alike.
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