15 Chicago Bike Tours to Plan a Day Around

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 with a local guide, stopping for Chicago-style hot dogs, deep-dish pizza, bakery treats and optional craft beer. The 4.5-hour day and evening routes cover different neighborhoods and landmarks, with guides such as Joe, Fran, Kevin and Anderson among the roster. Bikes, helmets, water and food are included; beer costs extra.

“This was a fun ride through Chicago, some neighborhoods, and along the lake. Food was delicious and portions were larger than I expected. We met some really nice people. The reason I’m giving 4 instead of 5 stars is that we didn’t get a lot information on Chicago, its history, or current issues. Nonetheless, all of us —- visitors and local — learned some things, enjoyed the food and company, and had a fabulous day on the ride!”

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2.Bike Tour of Chicago’s Lakefront Neighborhoods

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

Cycle about nine mostly flat miles from Lake Shore Drive through Lincoln Park, along Lake Michigan, and into Gold Coast and Old Town. Your guide handles the route and shares local stories, from the Great Chicago Fire to the Playboy Mansion. Bikes and helmets are included; allow three hours and be ready to ride in changeable weather.

“Actually cycling in a city with a confident guide making it all seem easy , Gold Coast was beautiful as was st micheals church .”

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3.Chicago’s Ultimate City Bike Tour

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

Ride with a guide from Bobby’s Bike Hike past the Field Museum, Shedd Aquarium, Soldier Field, Buckingham Fountain, Millennium Park, and more. The roughly three-hour outing includes a bike, helmet, and stops for stories and photos. Guides such as York, Dan, AJ, and Meredith have led tours, though your guide may vary. Expect a mostly flat ride, but not a route made only of bike paths.

“Great experiencie. Best way to know Chicago. We enjoyed it so much, the staff very professional. Good weather.”

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

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

Walk downtown with a local guide, stopping for deep-dish pizza, a Chicago hot dog, Italian beef, Garrett’s popcorn, and a sweet finish. The route links landmarks such as Millennium Park, Cloud Gate, the Riverwalk, and the Chicago Theatre on daytime tours. Your ticket also includes a two-hour bike or kayak rental, subject to seasonal and schedule limits.

“Our guide Jeff was incredibly knowledgeable, not only about the food we tried but about the history of the city, as well as the architecture. Jeff kept things moving and very upbeat throughout! I would rate Jeff as a five star guide! My husband and I just finished a two week tour of Greece and had many great guides during that time but Jeff was by far the best! Thank you Jeff from Rob and Shannon.”

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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 about 13 miles with a local guide, stopping for Chicago pizza, a hot dog and a brownie. Choose the daytime route toward Wrigley Field or the night ride past downtown landmarks. Bikes, helmets, water and food samples are included. A three-drink VIP upgrade costs $19.99.

“Our tour guide was the best she made the tour so enjoyable!!!”

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6.Lakefront Neighborhoods Bike Tour

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

Follow Chicago’s lakefront paths and near-north-side streets by bike, passing North Avenue Beach, Lincoln Park Zoo, Old Town, and Gold Coast mansions. A guide shares local history and city stories along the way. Bikes and helmets are included; the ride lasts three hours and costs $59 per person.

“Our guide was awesome! Very knowledgeable and passionate about Chicago as well as our safety! We loved everything about our Bike Hike. The bikes Were easy to handle for all ages and skills. It’s a fun way to see and travel through the city! Think no more about it! Book it! You will love it! We did!!”

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7.Chicago’s West Side Foodie Ride Bike Tour

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

Start near Navy Pier, then pedal through Fulton Market, the West Loop, Wicker Park, Bucktown, Ukrainian Village, and Old Town. Your guide leads a small group on a four-hour ride with enough tastings for a hearty lunch: burger, taco, pizza, pierogi, toffee, and chocolate. Bikes, helmets, and bottled water are included.

“The custard at the hamburger stop was off the chart good. Tour guide was very knowledgeable. Food was great.”

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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 Bobby’s Bike, Hike & Food Tours, stopping for Chicago-style pizza and other local bites while passing lakefront beaches, Millennium Park, Buckingham Fountain and more. A guide leads a group of up to 16, with bikes and helmets included. Expect a relaxed sightseeing pace, clear riding instructions and enough food to make a hearty lunch.

“Omar was fun, engaging and full of fun, historical facts about the Windy city. I would do this tour again in a minute!”

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9.Chicago Full Day Bike Rental

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

Pick up a bike at 540 N Lake Shore Drive and explore Chicago independently. Your rental includes a helmet, lock and city map, so you can plan a family-friendly route to Navy Pier, Millennium Park, Lincoln Park Zoo or Museum Campus. Return the bike to the same meeting point by 5pm.

“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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10.Ultimate City Attractions Bike Tour

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

This three-hour ride follows Chicago’s lakefront cycle paths past Buckingham Fountain, Millennium and Grant Parks, Burnham Harbor, Northerly Island and the Museum Campus. Your English-speaking guide shares city history and museum context. A bike and helmet are included; guides vary, with Gabriel among those known for resourceful commentary.

“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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11.Full-Day or Half-Day Bike Rental

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

Pick up a hybrid bike, Fuji Sportif 2.1 road bike or electric bike near Navy Pier, then explore Chicago on your own. Choose a four-hour or full-day rental and follow the Lakefront Bike Trail toward Millennium Park, Museum Campus or Lincoln Park. Helmets, locks and a city map are included; child bikes, seats and trailers are available.

“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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12.Westside Food Tasting Bike Tour with Guide

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

Spend four hours cycling from River North through Fulton Market, Ukrainian Village, Wicker Park, Lincoln Park and Old Town. You’ll sample neighborhood foods, hear stories about Chicago’s immigrant communities and ride the 606 and Lakefront trails. Guides on past tours have included Joe, Lou and Ashley. Food and bike are included; three drink pairings cost extra.

“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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13.Chicago Lakefront Electric Bike Tour

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

Ride with your own group on a private electric bike tour of Chicago’s lakefront, with helmets and bikes provided. Guide Anthony has led the route past Navy Pier, the Field Museum, the Adler Planetarium and Buckingham Fountain, stopping for photos and local context. The ride lasts about 45 minutes to an hour and starts and ends at 441 E Erie St.

“Getting a close view of all attractions in Chicago, while having fun on a electric bike. Our tour guide was great and he even stopped to take photos”

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14.Chicago Half-Day Bike Rental

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

Pick up a bike, helmet, lock and city map from Bobby’s Bike, Hike & Food Tours at 540 N Lake Shore Drive. Then spend about four hours exploring Chicago at your own pace, with options including Navy Pier, Millennium Park, Lincoln Park and Museum Campus. This is a self-guided rental, not a guided tour.

“Group of 11 rented bikes. One bike half way had a mechanical issue and they were excellent in helping us.”

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15.Chicago Amazing Lakefront Bike Tour

★★★★★★★★★★3.5 · 8 reviews · from $44

Start at 34 S Michigan Ave for an approximately two-hour guided ride along Chicago’s Lakefront Trail. You’ll pass lakefront parks, beaches, Navy Pier and the Lincoln Park area, with views of the skyline and Lake Michigan. A bike and helmet are included. The ride ends where it begins.

“Moderate level of activity, good trails, recreational. Hard to maneuver around crowds, suggest to take the earlier tours as crowds get thicker as the day passes specially on the popular spots”

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