Exploring Chicago's Roaring '20s: Art Deco, Gangsters, and Prohibition-Era Secrets Walking Tour
Difficulty
easy
Duration
2–3 hours
Fitness Level
Basic walking fitness is sufficient; the terrain is urban and mostly flat.
Overview
Discover Chicago’s vibrant 1920s with an immersive walking tour through Art Deco landmarks, gangster hideouts, and Prohibition-era stories that shaped the city’s colorful past.
Chicago in the Roaring '20s: Art Deco, Flappers, Gangsters, & Prohibition
Experience 1920s Chicago thru architecture! • 2 Hours • 1.5 Miles • All Ages
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Adventure Photos
About This Adventure
Discover Chicago of the Roaring '20s through its buildings & stories!
This tour is the answer to many requests for an Art-Deco-specific tour because — let's face it — we all LOVE the elegance, glam, and glitz of the 1920s. This 2-hour walking tour explores the interiors and exteriors of gorgeous buildings from this surprisingly brief architectural period in Chicago, with some interesting details and stories about life in that era. Flappers, gangsters, jazz, speakeasies — we'll pepper those throughout our larger exploration of Chicago's magnificent Art Deco buildings in order to truly set the context for you!
Inside Chicago Walking Tours brings you back in time on this much-anticipated tour. You’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. You’ll understand why the Art Deco style is so timeless — why even for us, it has a stunning beauty that inspires us to this day. In addition to experiencing magnificent Art Deco architectural interiors, you’ll also learn about Chicago’s notorious gangster history — even ending the tour inside an old gangster headquarters surrounded by real photographs, newspapers, and an old uncovered vault!
Let Inside Chicago Walking Tours take you back in time, and enjoy these interior spaces that evoke thoughts of Metropolis, The Great Gatsby, and even Gotham City (we’ll explain that one…). Staying almost entirely within the downtown Loop neighborhood, and ending just across the river in River North, we’ll explore the elegance of this fascinating period in Chicago’s history. Come join us on our newest tour!
Duration
2 Hours 1.5 miles on foot
Highlights of the Tour
- Great-Gatsby-esque interiors that throw you back in time;
- Stories of Capone's enemies and successors, with lots of archival photos & news articles;
- Gleaming marble, brushed metal, and other materials that celebrate the potential of the future;
- Much, much more!
Tour Details
- Runs rain or shine! We will be in touch in case of severe weather.
- Meeting Location: Refer to ticket confirmation for address.
Adventure Tips
Wear comfortable walking shoes
This tour covers multiple city blocks on pavement; sturdy shoes will keep you comfortable throughout.
Bring a water bottle
Stay hydrated as you explore outdoors, especially on warm days in the Loop district.
Check the weather forecast
Chicago weather can change quickly; dress in layers to stay comfortable during your walk.
Arrive early to explore nearby landmarks
Plan extra time before or after the tour to visit nearby sites like Millennium Park or the Art Institute of Chicago.
Local Insights
Wildlife
- Pigeons common in the Loop area.
- Occasional urban squirrels in local parks.
History
Chicago's Prohibition era shaped not only crime but also a booming underground culture that influenced the city's identity.
Conservation
The tour promotes walking to reduce vehicle carbon emissions and encourages responsible tourism in urban historic districts.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Essential for navigating city streets comfortably over several hours.
Weather-appropriate jacket
Fall in Chicago can be chilly and windy, so a light jacket keeps you warm.
fall specific
Sunscreen
Protect your skin during sunny days walking outdoors.
summer specific
Portable phone charger
Keep your phone charged for photos and GPS navigation throughout the tour.