CHICAGO · CYCLING TOURS

10 Chicago Cycling Tours to Book This Year

10 rides  ·  from $23 a head

This is the shortlist you would send a riding friend: 10 chicago cycling tours worth the money, each with its price, its distance and the one thing to know before you commit.

Bikes, Bites & Views: Chicago's Signature Dishes Bike Tour-Adults - Day route: Lincoln Park, Wrigleyville, and the lake
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Bikes, Bites & Views: Chicago’s Signature Dishes Bike Tour-Adults

Bike Tour of Chicago's Lakefront Neighborhoods - Lake Michigan and the Lakefront Trail
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Bike Tour of Chicago’s Lakefront Neighborhoods

2.Bike Tour of Chicago’s Lakefront Neighborhoods

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

Ride 9 miles along Chicago’s lakefront through Lincoln Park, Old Town, Gold Coast, beaches, and quiet neighborhoods with a local guide.

“Very good experience. Even with the heavy rain, the bike tour was maintained. It was great. Dan was our guide, the explanations were great. Thanks Dan !”

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Chicago's Ultimate City Bike Tour - Starting at Bobby’s Bike Hike on Lake Shore Drive
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Chicago’s Ultimate City Bike Tour

3.Chicago’s Ultimate City Bike Tour

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

Review of Chicago’s Ultimate City Bike Tour, with lakefront views, major sights, guide tips, pricing, safety, and booking advice.

“Meredith was the bomb? She knew the city like the back of her hand. She followed the safety precautions and made sure we kept up with everyone in our group. 10/10 recommend”

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Chicago: Classic Food & Walking Tour with Free Bike or Kayak - Starting with deep dish and Chicago food rules
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Chicago: Classic Food & Walking Tour with Free Bike or Kayak

Chicago: Bikes, Bites, and Views Biking Tour - Adults - Starting near Ohio Street and Lake Shore Drive
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Chicago: Bikes, Bites, and Views Biking Tour – Adults

Chicago Family Food and Bike Tour with Top Attractions - Starting along the Lake Michigan shoreline
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Chicago Family Food and Bike Tour with Top Attractions

7.Chicago Family Food and Bike Tour with Top Attractions

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

Ride Chicago’s lakefront, parks, and landmarks while tasting deep dish, hot dogs, Italian beef, and gelato on a four-hour family tour.

“We took our grandsons, ages 11 and 13, on the Chicago City and Food Tour. There were 8 others who joined our group. Joe was our guide and was great with the kids! We saw a lot of sights and sampled Chicago style pizza, hot dogs, and gelato. Overall, a great experience. The kids loved it and want to do it again which says it all!!”

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Chicago: Ultimate City Attractions Bike Tour - Riding Beside Lake Michigan
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Chicago: Ultimate City Attractions Bike Tour

8.Chicago: Ultimate City Attractions Bike Tour

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

See Chicago by bike on a three-hour lakefront tour through Millennium Park, Museum Campus, Northerly Island, and Grant Park.

“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 - Choosing the right bike for your Chicago day
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Chicago: Full-Day or Half-Day Bike Rental

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

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

Rent a bike near Navy Pier and explore Chicago’s lakefront, parks, museums, Lincoln Park, and Wrigley Field at your own pace.

“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: Westside Food Tasting Bike Tour with Guide - Fulton Market: from meatpacking to restaurant country
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Chicago: Westside Food Tasting Bike Tour with Guide

10.Chicago: Westside Food Tasting Bike Tour with Guide

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

Review of Chicago’s Westside Food Tasting Bike Tour, covering food stops, neighborhoods, biking, beer upgrade, value, and practical tips.

“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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