Find the best walking and bicycle tours in Chicago on Pelago. Plan and book online with the best prices and world class support.

The Best Walking and Bicycle Tours in Chicago | Updated February 2025

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.

chicago-millennium-park-self-guided-walking-tour_1

chicago-in-a-day-food-history-and-architecture-walking-tour_1

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.

walking-tour-underground-chicago-via-the-pedway-system_1

chicago-insta-walk-with-digital-and-polaroid-photoshoot_1

chicago-architecture-walking-tour-dazzling-interiorstm-of-the-loop_1

chicago-delicious-donut-adventure-by-underground-donut-tour_1

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.

chicago-favorites-food-walking-tour-with-bike-or-kayak-rental_1

bikes-bites-and-brews-chicago-s-signature-dishes-bike-tour_1

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.

chicago-walking-food-tour-with-secret-food-tours_1

chicago-small-group-city-tour-with-optional-architecture-river-cruise_1

chicago-pizza-tour_1

chicago-s-chinatown-food-and-walking-tour_1

chicago-walking-tour-historic-treasures-of-chicago_1

Experience the joy of gliding along Chicago's scenic lakefront discovering iconic landmarks like Buckingham Fountain and the Museum Campus while creating lasting memories with friends and family.

2-hour-chicago-lakefront-and-museum-campus-segway-tour_1

chicago-lakefront-and-museum-campus-small-group-tour_1

bike-tour-of-chicago-s-lakefront-neighborhoods_1

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.

chicago-architecture-walking-tour-the-underground-pedway-secrets-of-the-loop_1

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.

Get 10% off on the app with promo code APP10

The Best Walking and Bicycle Tours in Chicago

Chicago Millennium Park Self-Guided Walking Tour

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

Walking Tour: Underground Chicago via the Pedway

Chicago Insta Walk with Digital and Polaroid Photoshoot

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Chicago's Delicious Donut Adventure with Underground Donut Tour

Chicago Favorites Ultimate Food and Walking Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Chicago Walking Food Tour With Secret Food Tours

Chicago City Tour with Architecture River Cruise Option

Chicago Pizza Tour

Chicago's Chinatown Food and Walking Tour

Chicago Walking Tour: Historic Treasures of Chicago

2-Hour Chicago Lakefront and Museum Campus Segway Tour

Chicago Landmarks & Museum Campus Small Group Segway Tour

Bike Tour of Chicago's Lakefront Neighborhoods

Chicago Architecture Tour: Underground Pedway and the Loop

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

Chicago's Ultimate City Bike Tour

Chicago Walking Tour: A Walk Through Time