Chicago

15 Best Chicago Bike Tours

The lakefront rides: bikes-bites-and-brews food loops, neighborhood routes along eighteen miles of shoreline path and west-side foodie rides off the tourist grid. Chicago is flat, gridded and built for handlebars.

1.Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour

Experience Chicago’s iconic foods, neighborhoods, and lakeside views on a 4.5-hour bike tour with tastings of deep-dish pizza, hot dogs, brownies, and craft beer.

Most Popular★ 5.0

“Loved this experience !!! Our guide Joe C was excellent in guiding our group through different parts of the city and along Lake Shore Dr We enjoyed his witty and interesting commentary on the various historic points of interest. Food stops were well timed and…”

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2.Bike Tour of Chicago’s Lakefront Neighborhoods

Explore Chicago’s lakefront neighborhoods by bike with a knowledgeable guide, visiting iconic sights, hidden gems, and scenic parks in this 3-hour small-group tour.

★ 5.0

“Fran the guide was knowledgeable of the city, pleasant and kind. The weather was windy, rainy at time but the red was enjoyable .”

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3.Chicago’s Ultimate City Bike Tour

Discover Chicago on a 3-hour bike tour, visiting iconic landmarks along Lake Michigan, parks, and museums—an active, family-friendly way to see the city.

★ 5.0

“We had a fantastic time on this tour. Got to see a lot of sites, and learned some fun facts about the city along the way. AJ was our guy and is such a fun, and funny tour guide. This was our favorite of the…”

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4.Chicago: Classic Food and Walking Tour with Free Bike/Kayak

Discover Chicago's iconic flavors and sights on a 3-hour guided food tour, with free bike or kayak rentals, led by friendly, knowledgeable guides.

★ 4.9

“Some days ago, I took the Chicago Favorites Food & Walking Tour. I loved it. Not only was the food excellent, I also learned a lot from Julia, our guide, about the city. I really can recommend the tour.”

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5.Chicago: Bikes, Bites, and Brews Biking Tour

Discover Chicago's top neighborhoods, iconic sights, and famous foods like pizza, hot dogs, brownies, and beer on this 4.5-hour guided bike tour.

★ 4.9

“My wife and I first experience in Chicago after checking into our hotel. it was a great experience to get out, hear from our local tour guide Josey (Sorry, am not certain on the name spelling) some of what makes this city unique. We got…”

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9.Chicago Full Day Bike Rental

Discover Chicago at your own pace with a full-day bike rental, exploring iconic sights like Millennium Park, Navy Pier, and Wrigley Field comfortably.

★ 5.0

“Consiglio vivamente di fare l’esperienza in bici lungo la pista ciclabile del lago. Un metodo per vedere tanto in poco tempo. Abbiamo sfruttato appieno la giornata, grazie alle bici. I nostri figli 14 e 12 anni felicissimi. Visitato tutti i parchi lungo il lago senza…”

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11.Chicago: Full-Day or Half-Day Bike Rental

Explore Chicago at your own pace with a flexible bike rental. Ride along Lake Michigan, visit iconic sites, and enjoy scenic views—perfect for independent travelers.

★ 4.4

“Tutto molto bello. Peccato che l’orario di chiusura è alle 18:30 e non alle 20:00 come indicato nella descrizione.”

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12.Chicago: Westside Food Tasting Bike Tour with Guide

Discover Chicago’s vibrant neighborhoods on a 4-hour bici-food tour, sampling diverse cuisines, exploring historic sights, and enjoying scenic lakeside trails.

★ 4.8

“Joe was an amazing guide: professional, fun, engaging. The bikes were perfectly maintained! The route was lovely and the food was awesome (I appreciate the focus on smaller awesome non-chain vendors… we even happened to meet two owner!)”

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13.Chicago Lakefront Electric Bike Tour

Discover Chicago’s highlights on a private electric bike tour along the lakefront. Perfect for sightseeing, with stunning skyline views and personalized guidance.

★ 4.5

“Getting a close view of all attractions in Chicago, while having fun on a electric bike. Our tour guide was great and he even stopped to take photos”

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15.Chicago Half-Day Bike Rental

Explore Chicago on a flexible half-day bike rental, passing iconic sights like Millennium Park, Navy Pier, and Wrigley Field at your own pace for just $19.99.

★ 5.0

“Very fun family friendly activity on lake Michigan’s waterfront. Easy to find Bobby’s bike hike. Easy path for all types of riders.”

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