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The Best Walking tours in Chicago | Updated December 2025

Chicago

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Explore Chicago’s unique Pedway system featuring charming holiday decorations and iconic sights including Macy’s stunning Tiffany Ceiling and Millennium Park's festive tree and Cloud Gate sculpture.

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Immerse yourself in the cinematic world of 'Ferris Bueller's Day Off' while exploring iconic art pieces that enhance the film's narrative. Discover hidden connections within the Art Institute's treasures.

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Savor iconic Chicago-style hotdogs while exploring the city's rich food history. Experience hidden gems and famous eats all while discovering downtown landmarks and enjoying a unique culinary adventure.

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Savor iconic Chicago bites while surrounded by vibrant conversations and local charm highlighting the city's rich culinary history and engaging culture. Each dish tells a unique story.

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Discover Chicago’s hidden gems through stunning stained glass artwork while exploring the secretive underground pathways that connect the city’s architectural marvels and untold stories.

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Explore the colorful murals that bring Chicago's streets to life revealing hidden stories and artistic expressions waiting to be discovered. Experience the city's culture through its unique art scene.

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Explore the stunning geometry and intricate details of Chicago's Art Deco skyscrapers where historical significance meets architectural beauty in the heart of the financial district.

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The Best Walking tours in
Chicago

The Chicago Theatre Tour Experience

Chicago Walking Tour: Must-See Chicago

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Holiday Walking Tour: Underground Chicago via the Pedway

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Ferris Bueller Movie Tour at the Art Institute of Chicago

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Delicious Donuts & City Sights: Chicago's Original Donut Tour

Chicago Favorites Ultimate Food and Walking Tour

Chicago in a Day: Food, History & Architecture Walking Tour

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Chicago's Chinatown Food and Walking Tour

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Architecture Tour: Underground Pedway and the Loop

Haunted Chicago Booze and Boos Ghost Walking Tour

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Chicago Walking Tour: A Walk Through Time

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Chicago Walking Tour: Art Deco Skyscrapers Loop

Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters