Category Cycling Tours

Chicago · CYCLING TOURS

The 10 Cycling Tours in Chicago Worth Booking

10 reviewed

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

Bikes, Bites & Views: Chicago's Signature Dishes Bike Tour-Adults - Meeting point and pacing: how the 4.5 hours actually feel

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

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

Chicago’s 13-mile bike-and-food tour with deep-dish, Chicago dogs, brewery tastings, and famous sights, day or night.

“I had an afternoon to myself and live the outdoors so I booked the 4 hr bike, bites, and brews tour. I had a great time and was completely comfortable doing this tour by self as the guide was great and others in the group very friendly. Not overly strenuous at all, just a decent ride with plenty of stops to learn about Chicago.”

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Bike Tour of Chicago’s Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods - The ride plan: about 9 miles at a leisurely pace

2.Bike Tour of Chicago’s Lakefront Neighborhoods

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

Ride Chicago’s lakefront neighborhoods on a small-group 3-hour tour with bikes and helmets, hitting Lincoln Park, Gold Coast, and Old Town.

“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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Chicago’s Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour - Museum Campus hits: Field Museum area and the classic museum skyline

3.Chicago’s Ultimate City Bike Tour

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

Ride Chicago’s lakefront and museum campus on mostly car-free bike paths, hitting iconic parks, art, and major sights in 3 hours.

“Bike trip was lots of fun, tour guide was great and made the trip worthwhile. It rained part way through our trip but the guide had ponchos for everyone!”

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Chicago: Classic Food & Walking Tour with Free Bike or Kayak

Chicago: Classic Food & Walking Tour with Free Bike or Kayak - Where You Start: Two Downtown Meeting Options

Chicago: Bikes, Bites, and Views Biking Tour – Adults

Chicago: Bikes, Bites, and Views Biking Tour - Adults - Daytime vs nighttime: Wrigleyville or Buckingham Fountain

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

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

A 4.5-hour adults-only bike tour with Chicago’s top pizza, hot dogs, brownies, and beer, plus day sights at Wrigley or night at Buckingham.

“"The tour of Chicago was awesome. Greg, our guide, knew so much and was super fun to be around. He told us all these cool stories about the city that made everything really interesting. Greg was also really attentive, always checking in to make sure we were okay and answering all our questions. His love for Chicago was contagious, and by the end of the tour, we all felt like we had a new appreciation for the city."”

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Chicago: Lakefront Neighborhoods Bike Tour

Chicago: Lakefront Neighborhoods Bike Tour - From the Lake to Lincoln Park: Zoo Area to the Hefner Stop

6.Lakefront Neighborhoods Bike Tour

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

Ride Chicago’s lakefront neighborhoods in 3 hours with a guide, bike, and helmet for $59, hitting Lincoln Park, Old Town, and the Gold Coast.

“Jay was our guide and he was the best guide I’ve had!!! Very knowledgeable and personable! Absolutely loved this!”

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Chicago’s West Side Foodie Ride Bike Tour

Chicago's West Side Foodie Ride Bike Tour - Meeting point, start time, and the practical ride pace

7.Chicago’s West Side Foodie Ride Bike Tour

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

Bike Chicago’s West Side on a small-group food tour with generous tastings, lakefront views, and neighborhood stories.

“Ardarius was a great guide! Very knowledgeable and fun! We got some exercise, tried some new foods and drinks and had a great time!”

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Chicago Family Food and Bike Tour with Top Attractions

Chicago Family Food and Bike Tour with Top Attractions - The meeting point: start easy at Bobby’s Bike Hike

8.Chicago Family Food and Bike Tour with Top Attractions

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

Bike Chicago’s top sights and classic bites on a 4-hour family route along the lakefront, parks, Riverwalk, and more.

“never went on bike tour, was notified evening prior that tour guide got sick offered a walking tour and wasn't really compensated the difference of over 100$, was offered a couple of 6oz beer drinks. requested the vegetarian option but didn't expect to pay that much for an order of fries!”

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Chicago Full Day Bike Rental

Chicago Full Day Bike Rental - The lakefront ride to Navy Pier and the big-picture views

9.Chicago Full Day Bike Rental

★★★★★★★★★★5.0 · 49 reviews · 1 day (approx.) · from $29Best value

Rent a bike for a full day and cruise Chicago’s lakefront, from Navy Pier to Millennium Park and more, with helmet, lock, and map included.

“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 grossi sforzi.”

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Chicago: Ultimate City Attractions Bike Tour

Chicago: Ultimate City Attractions Bike Tour - Riding the lakefront: skyline views without the walking marathon

10.Ultimate City Attractions Bike Tour

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

Pedal Chicago’s best sights on safe cycle paths: Millennium Park sculptures, Northerly Island, Museum Campus views, and Buckingham Fountain.

“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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