Chicago
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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.

    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.

  • Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

    2. Bobby's Bike Hike Chicago: Lakefront Neighborhoods Tour

    Hop on a bike and explore Chicago's lakefront neighborhoods! Bobby's Lakefront Neighborhoods Bicycle Tour is Chicago's longest-running and most popular bike tour. Veer off the beaten path and into the opulent neighborhoods, pristine parks, and packed beaches of the near north-side of Chicago. Explore the Gold Coast mansions, Old Town historic district, Lincoln Park, and the zoo, all on the bike. Pass by North Avenue beach and Chicago's lakefront while an experienced, knowledgeable guide explains the rich history and culture of the area. This tour is designed for all ages and fitness levels. Safety is our top priority, and guests follow bike paths for a majority of the tour. Bikes and helmets are provided.

    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!!

  • Chicago: Westside Food Tasting Bike Tour with Guide

    3. 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-c...

    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!!!

  • Chicago: Downtown Family Food Tour by Bike with Sightseeing

    4. 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 y...

  • Chicago's Greatest Hits Bicycle Tour

    5. Chicago's Greatest Hits Bicycle Tour

    This tour takes you through some of Chicago's main sights by bicycle. Ride along the lakefront visiting parks and gardens as the refreshing lake breeze races across your face. Glide by Buckingham Fountain as it sprays high into the sky and reflects the sunlight. Coast through the green spaces and monuments of Millennium and Grant Parks, the Museum Campus and Burnham Harbor. As you cruise by, get a glimpse of some of the most popular attractions in Chicago while your guide shares their history and explain's the city's massive collections of historical artifacts that are unique to these world-renowned museums.  Finally, ride back as you view one of the world’s most beautiful skylines and its lovely lakefront, perfect at any time of the day.

  • Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

    6. 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.

Other Sightseeing Options in Chicago

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