Pedal through the Windy City’s diverse neighborhoods with expert-led bike tours that showcase Chicago’s architectural gems and hidden corners. From the bustling Magnificent Mile to the serene Lincoln Park trails, local operators like Bobby’s Bike Hike and Bike and Roll Chicago offer distinctive perspectives.
Savor deep-dish pizza stops on the Bikes, Bites, and Brews Tour, or explore spooky stories during the Haunted Bike Tour through River North. The Westside Food Tasting route reveals authentic Chicago flavors while the Friendly Neighborhoods Tour connects riders with local culture.
Discover Chi-town’s best bike tours below!
Featured Bike Tours in Chicago
- Bikes, Bites, and Brews Tour
- Bikes at Night Tour
- Bobby's Bike Hike
- Haunted Bike Tour
- Lincoln Park Bike Adventure
- Bike and Roll Chicago
- Friendly Neighborhoods Tour
- Westside Food Tasting Bike Tour
Chicago Guided Tours
Bike and Roll Chicago
What to Expect
Extensive bike rental options
Description
Bike and Roll Chicago offers a wide range of bicycle rentals and guided tours, including electric bikes, cruisers, and family-friendly options. Located at Millennium Park and Navy Pier, it provides easy access to Chicago's lakefront and riverfront bike trails. Tours highlight Chicago's history, architecture, and scenic views. The company also offers Segway tours and professional bike maintenance services.
Where: Chicago | More Info: Bike and Roll Chicago
Bikes at Night Tour
What to Expect
Nighttime skyline views
Description
This guided nighttime bike tour explores Chicago's illuminated attractions, including the Museum Campus, Buckingham Fountain's light show, and concludes with fireworks at Navy Pier. The tour offers stunning skyline views and a unique perspective on the city's iconic landmarks.
Where: Chicago | More Info: Bikes at Night Tour
Bikes, Bites, and Brews Tour
What to Expect
Chicago's signature dishes by bike
Description
This 4-hour guided bicycle tour explores Chicago's iconic dishes and neighborhoods. Participants sample deep-dish pizza, Chicago-style hot dogs, gourmet brownies, and local craft beers while cycling through historic areas like Wrigleyville and the Lakefront Trail. The tour offers a unique blend of culinary experiences and scenic city views.
Where: Chicago | More Info: Bikes, Bites, and Brews Tour
Bobby's Bike Hike
What to Expect
Award-winning guided bike and food tours
Description
Bobby's Bike Hike offers guided bike, walking, and food tours, showcasing Chicago's diverse neighborhoods and culinary scene. As America's longest-running city bike tour operator, it provides immersive experiences with a focus on local culture and cuisine. Tours include options like Bikes, Bites & Brews and Foodie Tours, catering to various interests and skill levels. The company also offers bike rentals and youth summer camps.
Where: Chicago | More Info: Bobby's Bike Hike
Friendly Neighborhoods Tour
What to Expect
Diverse neighborhood exploration
Description
Friendly Neighborhoods Tour offers a unique exploration of Chicago's diverse neighborhoods, highlighting cultural traditions, historical landmarks, and local businesses. This tour is particularly suitable for bicycle tour operators as it provides an opportunity to explore areas like Logan Square, Bronzeville, and Ukrainian Village, each with its own distinct character and attractions.
Where: Chicago | More Info: Friendly Neighborhoods Tour
Haunted Bike Tour
What to Expect
Haunted nighttime bike tour
Description
This haunted bike tour explores Chicago's spookiest spots, including the John Hancock Center, the SS Eastland shipwreck site, the Iroquois Theater, and the Congress Plaza Hotel. The tour combines historical tales of hauntings and tragedies with a nighttime bike ride through iconic landmarks and waterfront parks. It features a guided adventure that highlights the city's darker side.
Where: Chicago | More Info: Haunted Bike Tour
Lincoln Park Bike Adventure
What to Expect
Car-free lakefront trail exploration
Description
The Lincoln Park Bike Adventure offers a scenic tour along Chicago's car-free lakefront trail, exploring beaches, parks, lagoons, and Lincoln Park Zoo. This family-friendly tour includes top sights like Navy Pier, North Avenue Beach, and the Conservatory, providing a mix of nature and attractions.
Where: Chicago | More Info: Lincoln Park Bike Adventure
Westside Food Tasting Bike Tour
What to Expect
Cultural food tasting by bike
Description
This 4-hour guided bike tour explores Chicago's West Side, offering a culinary journey through diverse neighborhoods like Wicker Park and Bucktown. Participants taste local specialties such as Polish pierogis and award-winning tacos, with an option to upgrade to include local craft beer. The tour provides a unique blend of cultural exploration and gastronomic delights.
Where: Chicago | More Info: Westside Food Tasting Bike Tour