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The Best Walking tours in Chicago | Updated June 2025

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Experience the gritty charm of Chicago's past as you ride in a bus dedicated to the infamous stories of mobsters crime scenes and legendary figures from the city’s shadowy history.

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Explore Chicago's Millennium Park at your own pace discovering art and history through a personal audio guide while enjoying the beauty of this iconic urban landscape.

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Step inside a 125-year-old architectural gem and uncover the stories of Solon Spencer Beman's legacy. Experience the charm and history of Chicago's hidden treasure the Fine Arts Building.

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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

Frank Lloyd Wright Robie House Admission

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

Chicago Millennium Park Self-Guided Walking Tour

Chicago Insta Walk with Digital and Polaroid Photoshoot

Chicago Highlights Running Tour

Inside Tour of Chicago’s Fine Arts Building

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Chicago's Delicious Donut Adventure with Underground Donut Tour

Chicago Favorites Ultimate Food and Walking Tour

Chicago in a Day: Explore Food, History, and Iconic Architecture

Chicago Walking Food Tour With Secret Food Tours

Chicago's Chinatown Food and Walking Tour

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Architecture Tour: Underground Pedway and the Loop

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

Haunted Chicago Booze and Boos Ghost Walking Tour

Chicago Walking Tour: A Walk Through Time

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

Chicago Walking Tour: Art Deco Skyscrapers Loop

Downtown Chicago Walking Pizza Tour