Top Chicago Bike Tours

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Amazing skyline and lakefront views await on our Chicago Bike Tour. Experience the city’s beauty up close on a Bicycle Tour in Chicago that blends culture, history, and unforgettable scenery.

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

3 hoursFree Cancellation

4.9

(253)

from $59

Taste robust flavors on our Chicago Food & Bike Tour. Ride a Bicycle through the Westside and savor bold bites—one of the top Culinary Things to do in Chicago.

Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.

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Chicago's West Side Foodie Ride Bike Tour

4 hoursFree Cancellation

4.9

(114)

from $99

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

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Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

4 hours 30 minutesFree Cancellation

4.9

(755)

from $89

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

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Bike Tour of Chicago's Lakefront Neighborhoods

3 hoursFree Cancellation

4.9

(251)

from $59

Likely to Sell Out

2 Hour Chicago Landmarks & Lakefront E-Bike Tour

Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on our state-of-the-art electric bikes. From iconic landmarks to hidden gems, this unforgettable adventure combines adventure, warmth, and loads of fun. Immerse yourself in the vibrant atmosphere of Milton Olive Park, the wonder of Soldier Field, and capture unforgettable photos at the majestic Buckingham Fountain. With flexible routes and a focus on hidden treasures, our tour offers a truly unique and memorable experience through the heart of Chicago.

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2 Hour Chicago Landmarks & Lakefront E-Bike Tour

2 hoursFree Cancellation

4.6

(8)

from $72

Kid smiling faces say it all on our Family Friendly Chicago Food & Bike Tour. Ride a Bicycle, taste local favorites, and enjoy one of the best Kid-Friendly Things to do in Chicago.

Chicago Family Food and Bike Tour with Top Attractions

4 hoursFree Cancellation

4.8

(99)

from $79

Experience Chicago like never before—and see more of the sights in less time—on this immersive bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the one-of-a-kind Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory, and much more. The use of a bike and helmet is included.

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Chicago Amazing Lakefront Bike Tour

2 hoursFree Cancellation

3.4

(8)

from $49

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.

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Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

4 hoursFree Cancellation

5.0

(1)

from $179

Chicago Must-See Bike Tour with Iconic Photo Ops

Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local with your guide, dive into the bustling life of the business districts, be welcomed by the soothing green of the parks, and admire the lake scenery as you ride along the shore. The city boasts plenty of attractions and landmarks to discover, so the bike is a perfect way to save time to get there. Visit the most important landmarks of the city following your guide. Enjoy a safe bike trip around the city and get experience mainstream tours can’t offer. Be entertained with historical and cultural insights from your guide. The tour is great for families

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Bike Tour in Chicago

3 hoursFree Cancellation

3.5

from $129

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes provide effortless rides through the city, eliminating worries about traffic and parking. Experience the joy of biking while saving on gas and insurance costs. - Convenient location on Clark Street in Lincoln Park - Free demo test ride available - Ideal for leisurely exploration or thrilling rides - Expert advice to help you choose the right e-bike model

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Electric Bike Tours in Lincoln Park

2 hours 30 minutesFree Cancellation

from $85

Unforgettable Small Group Biking Tours from Chicago to Milwaukee

Our tours have varying difficulty levels to accommodate different skill levels. We take every safety precaution available to prioritize your well-being. Our routes that take you to must-see attractions and beautiful destinations. The Bahāʾī temple that we will pass is listed on the National Register of Historic Places and the only Bahāʾī place of worship in North America. This weekend vacation to Milwaukee is a vibrant mix of urban excitement and nature. Notable spots that riders can visit are the Milwaukee Art Museum, the National Bobblehead Hall of Fame Museum, and the Black Holocaust Museum. The city is also home to over 40 breweries, with iconic names like Schlitz and Pabst leading the way. On the ride you'll traverse mostly flat terrain that shifts between suburban areas and secluded bike paths. Expect southward winds along the lake, be prepared to experience some headwinds during your ride. Roads: 79% paved, 21% trails Distance: 74.6 miles Elevation: +963 ft/ - 1,058 ft

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Unforgettable Small Group Biking Tours from Chicago to Milwaukee

1 day 10 hoursFree Cancellation

from $349

Small Group Bike Tours From Chicago to Lake Geneva

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see landmarks such as the Gold Pyramid House and the stunning Bahāʾī temple. The 85-mile bike ride will bring you right to your boutique inn where your bags will be waiting for you. The following day your guide will take you to the beach where you can kayak or just enjoy some much-deserved lounging. After this you will visit the Apple Barn for a delightful day of seasonal apple or strawberry picking, followed by a stop at their bakery. Don't forget to bring your ID for the wine tasting; they often feature live music and are very family-friendly! Will give you time to explore the shops and ice cream parlors in the charming downtown area before packing the car to drive you back to Chicago.

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Small Group Bike Tours From Chicago to Lake Geneva

2 daysFree Cancellation

from $449

Per group

Top Attractions in Chicago

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Not seeing something you are looking for?

Cyclists rejoice! Chicago is a biking paradise with no shortage of wide, flat roads and bike lanes throughout. If you want to take full advantage of everything the city has to offer, you can’t go wrong with a Chicago bike tour. Take a guided ride along the picturesque lakefront, sample iconic local dishes and drinks on a tour, or spend the day riding to neighboring Milwaukee with a small group of other cyclists. Whatever your interests, Chicago has a bicycle tour to suit your needs.

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What are the best Chicago bike tours?

There are plenty of high-quality Chicago bike tours to choose from. Looking at ratings and reviews given by previous customers, these are the best tours available right now:

What are the most affordable Chicago bike tours?

Are guided Chicago bike tours worth it?

Yes, guided Chicago bike tours are absolutely worth it. Your guide handles all the logistics, and you'll hear stories and historical insights about the Windy City as you ride around. Plus, many tours include food tastings of Chicago classics like deep-dish pizza and hot dogs, giving you a taste of local culture as you explore the city's lakefront, parks, and iconic landmarks.

Per one customer who booked the Chicago Family Food and Bike Tour with Top Attractions, "The tour was such a fun experience! Loved that we got a true feel of the city while being active. The tour was very interactive and AJ and Andy were the perfect tour guides. The instructions were clear and the food was amazing! Would definitely recommend to anyone wanting to explore the city for the first time to book this food and bike tour!"

What should I know before booking Chicago bike tours?

Before booking your Chicago bike tour, consider what you want to get out of the experience—some tours focus purely on sightseeing, while others combine cycling with food stops so you can sample the local specialties. Check the tour duration, as options range from 2-hour rides around the city to full weekend adventures from Chicago to Milwaukee. Most tours include bike and helmet rental, but others don’t, so confirm this beforehand—and consider your fitness level since some tours cover significant distances.

What are the best tips for enjoying Chicago bike tours?

Dress comfortably in layers since Chicago's weather can be unpredictable. Opt for closed-toe shoes for safe pedaling, and don't forget sunscreen and a water bottle to stay hydrated on longer rides. Make the most of your local guide by asking questions about the sights you see and the neighborhoods you cycle through. Finally, if your tour includes food stops, arrive hungry and ready to try local classics like deep-dish pizza and Chicago hot dogs.

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Top Chicago Bike Tours

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