10 Chicago Cycling Tours Worth the Saddle Time

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

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

Spend about 4.5 hours cycling 13 miles through Chicago with a local guide, tasting deep dish pizza, a Chicago dog, bakery treats, and brewery samples. Day routes visit Lincoln Park, Wrigleyville, Old Town, and the Gold Coast. Night routes add the Riverwalk, Millennium Park, Buckingham Fountain, and lakefront views. Minimum age is 16.

“Kevin was a wonderful guide. He knew his history of Chicago very well. The food stops were all delicious and gave a great background of the city, as well. We felt safe throughout the tour biking down city streets, parks, and along the beach. Would totally do it again!”

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2.Bike Tour of Chicago’s Lakefront Neighborhoods

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

Spend about three hours cycling Chicago’s flat lakefront route with a guide such as Liam, Dan, Lou, or Jamal. You’ll ride about 9 miles, stop at Lincoln Park Zoo, North Avenue Beach, Old Town, Gold Coast, and St. Michael’s Church, and follow the Lakefront Trail. Bikes, helmets, and bag storage are included.

“Awesome Experience I've done many of these tours in the past, and they never get old, especially because each guide has a different perspective and how they present it to the group.”

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3.Chicago’s Ultimate City Bike Tour

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

Explore Chicago by bicycle with guides such as Dan, York, AJ, Meredith, and Nic. Ride a mostly flat route through Museum Campus, the lakefront, Grant Park, Millennium Park, and the Loop, stopping for history, photos, and skyline views. Bikes and helmets are included, and the group is limited to 15 riders.

“Great tour and Dan was very kind and well organised. Lots of insights perfect to understand and discover the city”

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

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

Sample deep dish, a Chicago dog, Italian beef, Garrett’s popcorn, and a brownie or gelato while walking from the Magnificent Mile to Millennium Park. Guides such as Jeff, Julia, James, and Gabe are known for lively city stories. Your ticket also includes a two-hour bike or seasonal kayak rental.

“Great experience, loved our guide, Gabe! Great way to enjoy a few hours, you won't regret it.”

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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 & Food Tours. Choose a daytime ride through Lincoln Park to Wrigley Field or a night route past Millennium Park and Buckingham Fountain. Your guide handles the route, safety, stories, bikes, helmets, and food stops. Guides such as Fran, Dan, and Josie are known for lively commentary.

“It was great biking in the neighborhoods and along Lake Michigan.”

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6.Lakefront Neighborhoods Bike Tour

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

Ride with an English-speaking guide through Chicago’s Gold Coast, Old Town, Lincoln Park, and lakefront parks. You’ll pass the Lincoln Park Zoo, North Avenue Beach, and Hugh Hefner’s original Playboy home while staying on bike paths for much of the route. Guides such as York, Daisy, Jay, and Heath bring local stories and humor to this three-hour outing.

“This was our first visit to Chicago and the tour was very informative. Daisy was a knowledgeable guide and did a great job.”

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7.Chicago Family Food and Bike Tour with Top Attractions

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

Ride about 9 miles through Chicago’s lakefront, Gold Coast, Loop, Lincoln Park, and Grant Park with guides such as AJ, Joe, Paul, or Brooke. Expect a comfort bike, helmet, city stories, and generous tastings of deep dish pizza, Chicago hot dogs, Italian beef, and gelato. Groups are capped at 16.

“This was so fun. We actually got a great tour of the city. We were even able to try great food and snacks along the way! Great job! ❤️👍🏽”

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8.Ultimate City Attractions Bike Tour

★★★★★★★★★★4.9 · 48 reviews · 3 hours · from $59

Ride Chicago’s lakefront cycle paths for three hours with a bike, helmet, and English-speaking guide. You’ll pass Buckingham Fountain, Millennium and Grant Parks, Burnham Harbor, Northerly Island, and the Museum Campus while learning about the city’s past. Guide Gabriel has earned praise for his useful local stories, and the route avoids regular city traffic.

“Amazing guide and tour. Bikes were excellent and gave us chance to see so much of the city you wouldn’t access on any other tour. Loved it!!”

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9.Full-Day or Half-Day Bike Rental

★★★★★★★★★★4.4 · 22 reviews · 1 day · from $23Best value

Pick up a hybrid, Fuji Sportif 2.1 road bike, or electric bike near Chicago’s Lakefront Bike Trail. Ride for four hours or a full day with a helmet, lock, and city map. Plan your own route to Navy Pier, Millennium Park, Museum Campus, Lincoln Park Zoo, or Wrigley Field. Junior bikes, trailers, and child seats are available.

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10.Westside Food Tasting Bike Tour with Guide

★★★★★★★★★★4.8 · 16 reviews · 4 hours · from $99

Ride from River North through Fulton Market, Ukrainian Village, Wicker Park, Lincoln Park, and Old Town while tasting pierogis, tacos, ice cream, toffee, and more. Your guide handles the route and city stories. Bikes, helmets, water, and food are included. Adults 16 and older can add three drink pairings for $19.99.

“Excellent tour! The bikes were good and easy to ride; the food was terrific and the tour guide was attentive, funny and knowledgeable. Highly recommend!!!”

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