Chicago
Bike Tours

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Our most recommended Chicago Bike Tours

Chicago: Bikes, Bites, and Brews Biking Tour

1. Chicago: Bikes, Bites, and Brews Biking Tour

Working up an appetite won’t be a problem on this signature bike tour combing city sightseeing with the best foods and brews in Chicago.Sample Chicago’s 4 favorite food groups – pizza, hot dogs, brownies, and beer. You’ll learn the history behind the iconic foods and also get a taste of some of Chicago’s most popular neighborhoods. On the daytime version of the tour, cruise through Wrigleyville, Gold Coast, Old Town, Lakeview, and Lincoln Park. On the nighttime version of the tour, bike through the skyscrapers and bars of downtown Chicago and see Millennium Park and Buckingham Fountain at night. On either route, enjoy the beautiful lakefront trail as well. This tour is 13 miles with perfect breaks along the way for sampling. Your experienced guide will keep you safe, in-the-know, and well-fed. Bikes provided.

Chicago Lakefront Bike Tour of Lincoln Park

2. Chicago Lakefront Bike Tour of Lincoln Park

The parks, skyline and lakefront of the Windy City are beautiful from any point of view. But they come alive when you can feel the wind in your hair. Bicycling along the Lakefront Trail and past beaches, lagoons and city landmarks is exhilarating, even at a casual pace. And our informative, entertaining tour guides make sure you have a good time. The route we follow starts at Millennium Park and includes the Lincoln Park Zoo and Conservatory, the Navy pier, Notebaert Nature Museum and North Avenue Beach. It is an easy 8-mile ride that takes about 3 hours. Our tour is designed for maximum enjoyment, not speed, so it makes a great outdoor activity for friends, families, couples or anyone who wants to see popular Chicago sights up close and personal.

Chicago: Downtown Family Food Tour by Bike with Sightseeing

3. Chicago: Downtown Family Food Tour by Bike with Sightseeing

Hop on a bike and enjoy this easy ride around Downtown Chicago to explore the cities best sights and food. Cruise through Millenium Park, Museum Campus and along the lakefront with regular stops to sample delicious treats as you go. Your guide will take you to some of the best spots to try deep-dish pizza, a true Chicago hot dog, Italian beef, and a dessert for good measure. Try them all (or their veggie alternatives) and learn about the foods that made Chicago famous. In between snacking, visit some of Chicago’s most popular downtown districts as you cruise through Grant Park (Buckingham Fountain), the Chicago Riverwalk, and more. Along the way, your guide will point out highlights like Navy Pier, the Magnificent Mile and the Chicago River. The stops are well-timed so, even though you’ll be working up an appetite, all ages and fitness levels can get involved and enjoy this ride. If you want the full experience, upgrade to the VIP Craft Beer Tour to enjoy beer pairings with many of the food stops.

Chicago: Westside Food Tasting Bike Tour with Guide

4. Chicago: Westside Food Tasting Bike Tour with Guide

Go around the world without leaving Chicago! Sample the best of Chicago’s West side neighborhoods decadent food options. Learn the stories of the immigrants from all over the world who helped make Chicago the city it is today, while tasting their delicious foods. Gaze at the historic homes, warehouses, and skyscrapers of Chicago's most historic neighborhoods. Ride along the new elevated 606 trail and the beautiful Lakefront Trail. Begin your tour in Chicago's bustling River North. Cross the iconic Chicago river, then ride through historic meatpacking district Fulton Market, now Chicago's restaurant and tech ground zero. Sample a delicious Mexican torta and a beer at a celebrity chef's new brewpub. Then ride past Google's new headquarters and some beautiful murals before arriving in Ukrainian Village, where you will taste the world's best Polish pierogis. From there, pass gorgeous 19th-century mansions before having another delicious ethnic snack in hipster hot spot Wicker Park. Bike along the new 606 trail, a bike path on a formal elevated rail line, and then sample some delicious ice cream and toffee in Lincoln Park. From there, head to quaint Old Town for a chocolate tasting, and finish off the tour with a beautiful ride down Chicago's world-famous Lakefront Trail.

Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

5. Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

Join Bobby’s Bike Hike as we unleash our Halloween "Fright" Hike bike tour through the city of Chicago! We’ll ride through a former cemetery where thousands of bodies are buried and visit the Chicago River site where 844 people drowned in the middle of broad daylight. It is believed that one man, Charley Porter, who was on the boat when it sunk, still haunts the area to this day. We’ll discuss Resurrection Mary, Chicago’s most infamous ghost, as well as explain some of Chicago’s most notoriously haunted locales from the Levee District to the Colombian Exposition and the exploits of the one and only H.H. Holmes.

Frequently asked questions about Chicago Bike Tours

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

4.8 / 5

based on 126 reviews

My wife and I first experience in Chicago after checking into our hotel. it was a great experience to get out, hear from our local tour guide Josey (Sorry, am not certain on the name spelling) some of what makes this city unique. We got to see, taste, and experience several venues, which DEFINITELY did NOT disappoint! Josey's enthusiasm, with the help of a few good patrons like ourselves really made this a great first experience to see the city and many of it's landmarks. I HIGHLY recommend this to newcomers and longtime residents alike. The knowledge and information given easily showed there is great history here

We loved our tour with Lou! The biking was super easy and fun. He took us down some great residential streets that felt safe and had great homes to look at. All the food was incredible! It did not disappoint! I loved that the food choices were not "traditional Chicago", but eclectic and representative of the various neighborhoods and vibes. We definitely felt like we got our money's worth and Lou was a great guide! Great way to see the city and it's neighborhoods.

Our tour guide was Thomas. The tour was very fun and the food was delicious. First stop was the deep dish pizza and craft beer. Very light to my surprise . Next the Chicago Hotdog and last the gelato. Lastly a beer. It was a great start to my first time in Chicago.

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!!!

Very nice experience if you like exercise, food and views