In the Summer of 2002, Arkansas-bred traveler Jeremy Lewno set down roots in Chicago, IL to carry on his father’s tradition of high-quality tours by starting Chicago’s #1 tour company.

BOBBY’S BIKE HIKE— Chicago Tour Company

Jeremy spent most of his twenties roaming Europe and became enchanted by bicycle exploration. Twenty-seven and strapped for cash, he opened Bobby’s Bike Hike, intent on inspiring Chicago visitors with the environmental & cultural benefits of bicycle tourism.

Bobby's Bike Hike Values

The company is named for Jeremy’s late father, Bob, a professional bus tour operator, who instilled in his son a love of education through travel, giving back to the community, health for the Earth and body, and the offering of unmatched service. These core values became the driving tenets of Bobby’s Bike Hike.


Bobby’s began by offering unique neighborhood bicycle tours, taking visitors off the beaten path and showing off the beautiful communities of Chicago.


Bobby’s added food stops to select bicycle tours, allowing guests to experience Chicago with all five senses.


Bobby’s Bike Hike launched food-sampling walking tours. Today, Bobby’s Bike Hike takes pride n offering world-class tours that balance education, safety, and unadulterated fun.


We offer a diverse array of guided biking tours, walking tours, food tours and craft beer crawls daily. The Bobby’s team of expert guides is excited to make your visit to Chicago an unforgettable adventure.

Traveler's Choice Award

best tour company in chicago on tripadvisor

Why Take a Guided Chicago Tour?

Good question! Did you know that the Second City is actually first when it comes to bike riding? Chicago consistently ranks at the top for both walking and biking because it’s flat and easy to access (take that NYC!). Plus, all the neighborhoods, parks, and attractions are connected through a network of sidewalks and trails. So it makes sense that the best way to experience life in Chicago is on two wheels (or two feet) alongside fun folks just like yourself.

And while it’s true that anyone can whizz from place to place in a car, bus, or boat, you miss out on soooo much. With a Chicago bike tour or a Chicago walking tour, or even renting a bike, you can actually hear the roar of Buckingham Fountain, touch the iconic lion statues at the Art Institute, and smell the Chicago-style pizza wafting through the air. Join us for a memorable Chicago tour – whether it’s a walking, bike, or food tour!