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What's Priceless?

Experience Chicago Family & Food Bike Tour of Top Attractions with Mastercard, which includes a complimentary locker rental to safely store your belongings while you savor deep-dish pizza and craft beer on this top-rated, four-hour bike adventure through iconic neighborhoods.

This could very well be the best family tour in Chicago. Why? Nothing beats the freedom of a bicycle to explore so many unique parts of Chicago and the distinctive tastes of classic Chicago foods.

This family-friendly tour explores Chicago’s vibrant North Side neighborhoods and then takes riders south to downtown sites. The stops are perfectly timed so that all ages and fitness levels will enjoy themselves. So bring the family!

We’ll be sampling from each of Chicago’s well-known and unique foods, including deep-dish pizza, a true Chicago hot dog, and a dessert for good measure. 

You’ll learn the history behind the foods that made Chicago famous and also get a taste for some of Chicago’s most popular downtown districts as we cruise through Millennium Park, Grant Park (Buckingham Fountain), Museum Campus, the Chicago Riverwalk, and along the lakefront. Come taste the best of Chicago’s staple foods while exploring more and having a blast on two wheels! All food samples included in the ticket price.

This tour is great for families on vacation or staycation, birthdays, or anyone looking to have an unforgettable time! Riders must be 8 years and older to ride their own bike, but we do have child equipment for younger riders as well.

What to expect:

Our Chicago Family Food & Bike Tour combines the flavorful satisfaction of city food tours with the fun of biking city paths! Bypass the wait at some of the city’s most popular restaurants, and focus on enjoying amazing food while getting in fun family time.

Start in Downtown Chicago

The journey begins at our downtown headquarters, where our entertaining and enthusiastic guides will introduce you to our incredibly bike-friendly city streets, via protected bike lanes and bike paths. The tour then rolls through Streeterville, past the Magnificent Mile shopping district, and into the high-end Gold Coast neighborhood for some world-famous Chicago-style deep-dish pizza.

A Windy City tradition since 1943, deep-dish pan pizza has been pleasing crowds for generations. Thick, buttery crust and loads of melted mozzarella are guaranteed. You’ll learn all about how this goliath pie is made and taste why it’s become a global phenomenon!

Then we’re off to taste Chi Town’s paramount ketchup-free sandwich— The Chicago-style Hot Dog. Pure Vienna Beef, poppy seed buns, and all the fixings create a totally unique culinary experience.

Chicago Riverwalk and Millennium Park

The next leg of the adventure travels safely along protected bike lanes, through the downtown skyscrapers, over to the Chicago Riverwalk for a stop at a traditional ma-and-pa establishment serving up what could be considered the best Gelato in the City. Yummy goodness.

We’ll take a small break in Millennium Park, where you can explore Cloud Gate (aka ‘the bean’), Pritzker Pavilion, and Crown Fountain. After Millennium Park, we’ll ride past Grant Park, Museum Campus, and Buckingham Fountain before stopping for a delectable dessert treat.

Final Stretch

On the final stretch of our trip, you’ll see how Chicago maintains our reputation as one of the country’s best (and most unexpected) beach towns. Sand, skyline, and clear blue water provide unmatched views for the end of our journey.

The tour finishes back at Bobby’s headquarters, after 4 hours and 10 miles worth of fun.

What's Priceless?

Experience Chicago's Westside Foodie Bike Tour worry-free with Mastercard, which includes a complimentary locker rental to safely store your belongings while you savor deep-dish pizza and craft beer on this top-rated, four-hour bike adventure through iconic neighborhoods.
Working up an appetite won’t be a problem on this tour, rated the best Chicago sightseeing bike tour of 2023 by TripAdvisor, and rated Top 20 Food Tour in the World by TripAdvisor!

Hop on a bike and discover a whole new side of Chicago dining in the westside! On this Chicago culinary tour, taste your way through diverse neighborhoods as we explore Chicago’s immigrant history through food. Enjoy the local eateries and unique foods that make Chicago such an amazing and delicious place to live. Tour Chicago’s westside by bike with restaurant pit stops along the way and a cultural experience you’ll remember!

All food and non-alcoholic beverage samples included in ticket price.

What to expect:

On this popular Chicago food tour, you will embark upon an exciting bicycle adventure through the vibrant West Side neighborhoods of Chicago. Inspired by some of the Windy City’s most prominent immigrant communities and original recipes, this tour showcases a fresh perspective of our diverse town.

Bypass the wait at some of the city’s most popular restaurants and focus on enjoying amazing food and beverages! The best burgers on the planet, craft beer optional upgrade, Polish pierogi, gourmet barbecue sandwiches, Swedish liqueur (optional upgrade), and rich gourmet chocolate flavor this thirteen mile ride with authentic Chicago-style. Our enthusiastic local tour guides will lead you through an unforgettable afternoon of history and cuisine, sure to make memories that will last a lifetime.

The journey begins at the Bobby’s Bike Hike headquarters, where you’ll meet your fun-loving and safety-conscious tour guide.

From there, you’ll bike up to a beautiful view of The Chicago River, a critical component of the city’s growth and development. You’ll ride through our famous lower streets like they do in The Dark Knight films, and then roll by the upscale eateries and nightclubs of River North.

The first stop on the tour is the Fulton Market district, formerly home to meat packing and produce distribution companies. The area is now heavily sought-after real estate for tech giants, young startups, and trendy new restaurants.

Here you’ll feast on delicious Led Zeppelin sliders served with award-winning local craft beer. The brews vary with season, but always deliver on creativity and nuanced flavor.

From Fulton Market, the tour will ride into Ukrainian Village, home to a wide range of highly esteemed Eastern European eateries. You’ll taste three different Polish pierogi, guaranteed to satisfy any cravings for savory stuffed pastries.

Next up is Wicker Park, a well-known Chicago artists’ community. The food of this area is just as creative as the residents. While you’re here, you’ll enjoy a tasty, authentic taco that was recently ranked ’50 best tacos in America.’

Adjacent to Wicker Park is Bucktown, where you’ll enjoy a ride through amazing old homes mixed with modern mansions.

After that, you’ll head back over the river into Old Town, a historic Chicago neighborhood that began as an artists’ haven. You’ll experience one of Chicago’s finest chocolatiers, and sample their rich, decadent drinking chocolate before heading back downtown.

The final leg of your journey is a beautiful ride alongside Lake Michigan. Catch a glimpse of the beaches and the skyline that define this beautiful town, and be a part of the city’s vibrant bicycle culture while cruising the wide Lakefront Trail.

After thirteen miles and four hours, the tour wraps up back at Bobby’s headquarters in Streeterville.