Founded in 2002, we were one of the first guided bike touring companies in the country and we consistently rank as the #1 sightseeing tour on Tripadvisor. Why? We’ve combined our knowledge as a second-generation tour operator with our drive and passion for tourism and travel. We've created one-of-a-kind Chicago bike tours, Chicago food tours and Chicago walking tours that speak to a variety of ages, interests, and skill levels.

Our tour guides are some of the most experienced in the business. We take extra care to find guides that are personable, knowledgeable and most importantly, FUN. In addition, our guides take your safety very seriously. They know the sidewalks and pathways inside and out so you’ll always be on the best route.

We invite you to find a tour that matches with your unique interests. We provide many variations to appeal to different people. Foodies, exercise junkies, history nuts — we have tours to please everyone. Our dynamic guides present information and fun tidbits even lifelong Chicago residents may not know. Our Chicago guided tours aim to keep you amused and absorbed in everything along the way. Our guides will make your tour an experience you won’t forget!

Bobby’s Bike Hike is the longest running city bike tour company in the country, offering award-winning tours for a variety of ages, interests, and skill levels. Our entertaining guides will take you to Chicago’s most popular neighborhoods and parks, as well as Chicago’s top attractions. Out bike tours consist of the classic Chicago bike tours as well as our electric bike tours which make it feasible for everyone to bike Chicago!

Bobby’s Bike Hike sets the standard in Chicago Food Tours. Whether by biking or walking, our food tours will let you experience the best of Chicago through your belly. We offer tours of Chicago classic dishes as well as unique ethnic eateries for a one of a kind Chicago culinary tour. All food and beverage samples are included in the ticket price. Bring your appetite!

Bobby’s Bike Hike offers top-rated Chicago walking tours designed to help you better orientate yourself, learn interesting stories, and meet amazing folks from all over the globe. Our entertaining guides set the standard and make sure your experience is top notch on your Chicago tour!

Want to explore on your own? No problem, rent a bike! Chicago proudly ranks as the country’s best city for bicycling year after year because of its flat terrain, miles of bike trails and interconnected neighborhoods, parks, and attractions. We’re conveniently located in the heart of Chicago’s 20-mile Lakefront Bike Trail and offer free locks, helmets, and maps. BOOK ONLINE FOR A 10% DISCOUNT!