8 Cycling Tours in Chicago Worth Booking

1.Bikes, Bites & Views: Chicago’s Signature Dishes Bike Tour-Adults

★★★★★★★★★★5.0 · 732 reviews · 4 hours 30 minutes (approx.) · from $89Our pick

Ride about 13 miles through Chicago with guides such as Joe, Fran, Kevin, and Lauren, stopping for deep-dish pizza, a Chicago dog, bakery treats, and optional craft beer. Choose a daytime neighborhood route or an evening ride past Millennium Park, Buckingham Fountain, and the lakefront.

“Was one of the best tours I’ve ever been on. Was doing a cross country solo train trip and they made me feel so welcome! Super fun!”

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2.Bike Tour of Chicago’s Lakefront Neighborhoods

★★★★★★★★★★5.0 · 241 reviews · 3 hours (approx.) · from $59Best value

Ride about 9 mostly flat miles from Lake Shore Drive through Lincoln Park, Old Town, and the Gold Coast, with stops at the zoo, North Avenue Beach, St. Michael’s Church, and the Lakefront Trail. Bikes, helmets, and a local guide are included.

“Great way to see places that otherwise you would not visit. Outstanding guide (Lou), so much fun and knowledgeable. Do it!”

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3.Chicago’s Ultimate City Bike Tour

★★★★★★★★★★5.0 · 233 reviews · 3 hours (approx.) · from $59

Ride with Bobby’s Bike, Hike & Food Tours from Lake Shore Drive through Museum Campus, Grant Park, Millennium Park, and the Loop. Expect a mostly flat route, city stories from guides such as Dan, York, AJ, and Meredith, and about 7 to 10 miles of actual riding within a three-hour tour.

“Good tour. York our tour guide was excellent. He was friendly and knowledgeable. All the staff were courteous and professional.”

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4.Classic Food & Walking Tour with Free Bike or Kayak

★★★★★★★★★★4.9 · 145 reviews · 3 hours · from $84

Spend three relaxed hours tasting deep dish, a Chicago dog, Italian beef, brownie or gelato, and Garrett’s popcorn while your local guide leads you through downtown sights. Guides such as Jeff, Julia, James, and Gabe are known for lively city stories. Your ticket also includes a two-hour bike or kayak rental.

“Gabe made it so fun & interesting. Felt very safe. He was great at navigating around crowds, etc. We plan on repeating this tour with friends!!”

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5.Bikes, Bites, and Views Biking Tour – Adults

★★★★★★★★★★4.9 · 141 reviews · 4h 30m · from $89

Spend 4.5 hours cycling Chicago with Bobby’s Bike Hike, stopping for pizza, a Chicago hot dog, brownie, and optional beer pairings. Daytime rides reach Wrigley Field, while evening tours visit Millennium Park, Buckingham Fountain, and Museum Campus. Bikes, helmets, water, food, and an English-speaking guide are included.

“I had such a blast doing the tour and we learned new tidbits about Chicago and found unique spots that I never knew existed in Chicago. Dan was great and so knowledgeable and engaging! Thanks a million! My parents and I loved it!”

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6.Lakefront Neighborhoods Bike Tour

★★★★★★★★★★4.9 · 123 reviews · 3 hours · from $59

Ride Chicago’s near north side with guides such as York, Daisy, Jay, and Heath. Over three hours, you’ll see Gold Coast mansions, Old Town, Lincoln Park Zoo, North Avenue Beach, and the lakefront, mostly on bike paths with some city-street riding.

“Very nice tour with Heath: lots of insights from a local guide: tour went a bit off the beaten track (which was good as had already seen those). His explanations were very humorous (almost stand up comedy). Very good attention to safety. I would surely recommend booking Heath as your bike tour guide. Smullie - The Netherlands”

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7.Chicago’s West Side Foodie Ride Bike Tour

★★★★★★★★★★5.0 · 112 reviews · 4 hours (approx.) · from $99

Join a small group of up to 14 for a four-hour Chicago bike-and-food tour from Streeterville through Fulton Market, West Loop, Wicker Park, Bucktown, Ukrainian Village, and Old Town. Guides such as Wyatt, Joe, Tryfon, Lou, and Gabe lead the ride, with enough tastings for lunch.

“I absolutely loved this west side bike ride! I did another one last time I was in the area. Good food, good people, and good brews 😋💕 Feel safe since you are with a group and the guides are all knowledgeable!”

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8.Chicago Family Food and Bike Tour with Top Attractions

★★★★★★★★★★5.0 · 98 reviews · 4 hours (approx.) · from $79

Ride about nine miles with a guide through Chicago’s lakefront, Gold Coast, parks, Riverwalk, Millennium Park, Grant Park, and Navy Pier. The four-hour tour includes bike, helmet, and enough samples of deep dish, hot dogs, Italian beef, and gelato to make a hearty lunch.

“This was a lot of fun riding through the city streets and to see all lights at night. Mark was our guide and he was great! The night our family took the tour was a night that Navy Pier shot off fireworks, so that was an additional bonus. Our family enjoyed very much, so I would say it was well worth the cost and would recommend that anyone who enjoys riding should work this in to their agenda. The only concern I would voice is that I believe one guide to be responsible for 20 bikers at night is too much responsibility! I would recommend that an additional guide be…”

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