Category Cycling Tours

Chicago · CYCLING TOURS

The 15 Cycling Tours in Chicago Worth Booking

22 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 $29

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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Chicago: Full-Day or Half-Day Bike Rental

Chicago: Full-Day or Half-Day Bike Rental - Your ride choice: hybrid, Fuji Sportif 2.1 road, or electric

11.Full-Day or Half-Day Bike Rental

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

Bike rental in Chicago: Lakefront Trail or Lincoln Park. Helmet, lock, and map included for $23. Choose 4 hours or full day.

“inadmissible il a fallu payer 20$ supplémentaires pour pouvoir récupérer les vélos car il y avait un équipement enfant dans la location alors qu’on en voulait pas pourquoi payer plus ???? sur le bon de réservation on avait jusqu’à 17h pour les restituer mais sur place l’heure était passée à 14h donc nous ne passerons plus par votre site avec Viator cela n’est jamais arrivé”

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Chicago Lakefront Electric Bike Tour

Chicago Lakefront Electric Bike Tour - Getting Your Bearings: The Starting Point That Actually Matters

12.Chicago Lakefront Electric Bike Tour

★★★★★★★★★★4.5 · 16 reviews · 45 minutes to 1 hour (approx.) · from $69

A private Chicago lakefront e-bike tour to hit Navy Pier, the Field Museum, Adler Planetarium, and Buckingham Fountain fast with an expert guide.

“Conflicting directions on the app for where to arrive and meet up. One address was a parking garage. The description said to find them near the Buckingham fountain; which was not near the 411 E Erie St meeting place. Yes, I went to both places and back to the first place about 12:50 to find no bikes or group or indication of a bike ride. Thus, I requested a full refund which I hope was granted. I have used Viator for many excursions and this was a famous first. Instead of accepting the confusion of two different sets of directions of where to meet up; I was found at fault…”

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Chicago: Westside Food Tasting Bike Tour with Guide

Chicago: Westside Food Tasting Bike Tour with Guide - Starting at River North and crossing the Chicago River

Chicago Half-Day Bike Rental

Chicago Half-Day Bike Rental - The Route You Can Actually Use: Lakefront, Parks, and Big Names

15.Chicago Half-Day Bike Rental

★★★★★★★★★★5.0 · 10 reviews · 4 hours (approx.) · from $19Best value

Rent a bike in Chicago for $19.99 for a half-day self-guided loop along Lake Michigan to top sights like The Bean and the zoo.

“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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