• Gold Coast - Lou Malnati’s Pizzeria - Deep-dish pizza is more than just a meal—it’s an experience. During the Chicago Food & Bike Tour, families can enjoy layers of gooey cheese, rich tomato sauce, and a buttery crust baked to perfection. Deep dish was invented in Chicago in the 1940s, and locals know it’s meant to be savored, not rushed.

On this delightful Bicycle Tour in Chicago, kids are thrilled to see the first slice lifted high with cheese stretching endlessly. It’s fun, filling, and truly unforgettable.

For those seeking standout Kid-Friendly Things to do in Chicago, combining downtown sightseeing with authentic Chicago deep-dish pizza offers the ultimate family adventure—active, interactive, and full of iconic flavor.

• Portillo’s & Barnelli’s Chicago - Chicago-style hot dogs are a must on the Chicago Food & Bike Tour. Families can enjoy this iconic favorite topped with mustard, neon relish, onions, tomato, sport peppers, a pickle spear—and absolutely no ketchup! Locals take this rule seriously, making it a fun tradition for kids to learn about.

On this flavorful Bicycle Tour in Chicago, the hot dog stop is a highlight—quick, delicious, and full of personality.

For those looking for unforgettable Kid-Friendly Things to do in Chicago, combining downtown sights with an authentic Chicago-style hot dog makes this tour the perfect blend of culture, flavor, and family adventure.

• Millennium Park - Millennium Park is a family favorite on the Chicago Food & Bike Tour. Ride into this vibrant downtown space where kids can splash at Crown Fountain, see their reflections in Cloud Gate, and run across open green lawns framed by the skyline. The park was built over old rail lines, transforming industrial space into one of the city’s most creative gathering spots.

On this lively Bicycle Tour in Chicago, wide paths and open plazas make riding easy and fun for all ages. Guides share quick, engaging stories that keep kids curious without slowing the adventure.

Among the top Kid-Friendly Things to do in Chicago, Millennium Park blends art, movement, and iconic views—plus delicious Chicago classics along the way for the ultimate family experience.

• Lakefront Trail - The Lakefront Bike Trail is the ultimate playground for families visiting the city. On the Chicago Food & Bike Tour, you’ll cruise this scenic path with Lake Michigan on one side and the skyline rising on the other—wide, safe, and perfect for riders of all ages. The lakefront was intentionally preserved for public use, giving families front-row access to beaches, boats, and unbeatable city views.

On this unforgettable Bicycle Tour in Chicago, kids feel the freedom of open paths while parents soak in the scenery—and everyone earns those delicious bites of classic Chicago favorites along the way. It’s active, safe, and packed with energy.

For those looking for truly memorable Kid-Friendly Things to do in Chicago, riding the Lakefront Trail while tasting iconic foods is the perfect blend of adventure, culture, and family fun.

• Buckingham Fountain - Buckingham Fountain is a showstopper for families on the Chicago Food & Bike Tour. Ride into Grant Park and watch one of the largest fountains in the world send water soaring high above the skyline. The top-of-the-hour burst is the moment kids love most—when the central jet shoots dramatically into the air.

On this scenic Bicycle Tour in Chicago, wide park paths make for smooth riding while guides share fun facts about how the fountain represents Lake Michigan and the four states that border it.

For those looking for unforgettable Kid-Friendly Things to do in Chicago, Buckingham Fountain delivers big views, open space to move, and classic city energy—plus tasty food stops that keep the whole family smiling.

• Navy Pier - Navy Pier is pure family excitement on the Chicago Food & Bike Tour. Ride along the lake and spot the towering Centennial Wheel, colorful boats, and nonstop waterfront energy. The pier began as a shipping hub in 1916 before transforming into one of the city’s most fun-filled destinations.

On this lively Bicycle Tour in Chicago, wide lakefront paths keep riding safe and smooth for all ages, while guides share bite-sized stories that make history feel like adventure. Kids love the open views, fresh breeze, and carnival-like atmosphere.

Among the most exciting Kid-Friendly Things to do in Chicago, experiencing Navy Pier by bike blends skyline scenery, movement, and delicious Chicago favorites into one unforgettable family outing.

• Chicago Riverwalk - The Chicago Riverwalk is where architecture and adventure meet. On the Chicago Food & Bike Tour, families ride above the river while spotting historic bridges, boat tours, and towering skyscrapers lining the water. The river once flowed the opposite direction—an engineering feat that changed the city’s future and still amazes kids today.

On this dynamic Bicycle Tour in Chicago, guides turn big history into fun, bite-sized stories while you cruise smooth downtown paths. The energy of the Riverwalk keeps everyone engaged—and hungry for the next classic Chicago treat.

For those looking for unforgettable Kid-Friendly Things to do in Chicago, exploring the Riverwalk by bike blends learning, movement, skyline views, and delicious local flavors into one action-packed family experience.

• Grant Park - Grant Park is Chicago’s backyard—and families feel it the moment they ride in. On the Chicago Food & Bike Tour, you’ll cruise wide, open paths framed by skyline views and lake breezes. This historic green space was intentionally kept “forever open, clear, and free,” making it the city’s front yard for festivals, celebrations, and everyday play.

On this relaxed and scenic Bicycle Tour in Chicago, kids love the space to ride comfortably while parents enjoy the iconic downtown backdrop. It’s fresh air, movement, and big-city energy without the traffic stress.

Among the most memorable Kid-Friendly Things to do in Chicago, exploring Grant Park by bike—paired with classic Chicago eats—creates the perfect balance of culture, outdoor fun, and family bonding.

• North Avenue Beach - North Avenue Beach is a family favorite and a highlight of the Chicago Food & Bike Tour. Ride along the lake with skyline views that look straight out of a postcard while kids watch volleyball games, boats cruising by, and the iconic boat-shaped beach house. This is one of the best panoramic skyline angles in the city—especially when you glance south toward downtown.

On this energetic Bicycle Tour in Chicago, the wide, smooth Lakefront paths make it easy and safe for riders of all ages. It’s open space, fresh air, and nonstop photo ops.

For those searching for unforgettable Kid-Friendly Things to do in Chicago, North Avenue Beach delivers that perfect mix of movement, scenery, and classic Chicago fun—plus delicious bites along the way.

• Gold Coast - Gold Coast Mansions add a touch of wow-factor to the Chicago Food & Bike Tour. As you ride past grand historic homes and tree-lined streets, kids get to see how Chicago’s wealthiest families rebuilt in style after the Great Fire. This neighborhood transformed from ashes into one of the most elegant areas in the country—making it a living lesson in resilience and architecture.

On this engaging Bicycle Tour in Chicago, families cruise safely through shaded streets while guides share fun stories about famous residents and hidden details most visitors miss. It’s history without the boredom.

Among the most enriching Kid-Friendly Things to do in Chicago, exploring the Gold Coast by bike blends storytelling, movement, and city charm—plus delicious stops that keep everyone smiling along the way.

• Oak Street Beach - Oak Street Beach is where city skyline meets sandy shoreline—and families love it. On the Chicago Food & Bike Tour, you’ll ride right along this vibrant stretch of lakefront where kids can spot sailboats, feel the breeze, and snap skyline photos just steps from the water. This beach sits at the crossroads of downtown energy and Gold Coast elegance, making it one of the most scenic stops in the city.

On this fun-filled Bicycle Tour in Chicago, the wide lakefront paths make riding safe and stress-free for families, while the open views keep everyone engaged. It’s fresh air, movement, and excitement all in one.

Among the top Kid-Friendly Things to do in Chicago, exploring Oak Street Beach by bike blends adventure, scenery, and delicious local eats into one unforgettable family experience.

• The Art Institute of Chicago - The Art Institute of Chicago is a cultural gem families recognize instantly. On the Chicago Food & Bike Tour, you’ll ride past the iconic bronze lions guarding this world-renowned museum while kids hear fun stories about masterpieces inside. The building dates back to the 1893 World’s Fair, making it a true piece of Chicago history.

On this engaging Bicycle Tour in Chicago, downtown paths make it easy to explore safely while guides turn big art history into memorable, kid-friendly moments.

For those searching for enriching Kid-Friendly Things to do in Chicago, seeing the Art Institute by bike blends culture, architecture, movement—and delicious classic Chicago eats—into one unforgettable family adventure.

• Lincoln Park - Lincoln Park is where families get the best of nature and city in one place. On the Chicago Food & Bike Tour, you’ll ride through this massive green oasis filled with open fields, shaded paths, and lakefront views. The park was once the site of the city cemetery before being transformed into one of the largest urban parks in the country after the Great Chicago Fire.

On this refreshing Bicycle Tour in Chicago, kids enjoy smooth, scenic riding while guides share quick, fun stories that bring the park’s past to life.

Among the top Kid-Friendly Things to do in Chicago, exploring Lincoln Park by bike—paired with classic Chicago favorites—creates an unforgettable mix of fresh air, history, and delicious family fun.

• The Chicago Theatre - The Chicago Theatre is pure “wow” for families. On the Chicago Food & Bike Tour, you’ll roll into The Loop and see the legendary marquee glowing above State Street—one of the most photographed signs in the city. This 1921 landmark once hosted vaudeville acts and movie premieres, making it a living piece of Chicago entertainment history.

On this exciting Bicycle Tour in Chicago, kids love spotting the bright lights while guides share fun stories about performers and downtown’s golden age. It’s big-city energy without the overwhelm.

For those searching for memorable Kid-Friendly Things to do in Chicago, seeing the Chicago Theatre by bike blends history, architecture, and classic city excitement—plus tasty food stops that keep the whole family happy.

• Millennium Hall - A sweet Chicago dessert is the perfect finale on the Chicago Food & Bike Tour. After cruising downtown sights, families enjoy a local favorite—whether it’s rich chocolate, a classic bakery treat, or a famous Chicago confection. Dessert is part of the city’s food culture just as much as pizza and hot dogs.

On this flavorful Bicycle Tour in Chicago, kids light up when it’s time for that final bite. It’s the reward after a fun, active ride through iconic neighborhoods.

Among the tastiest Kid-Friendly Things to do in Chicago, pairing sightseeing with a delicious Chicago dessert turns this tour into more than a ride—it’s a full family experience everyone remembers.

• Cloud Gate - Cloud Gate—better known as “The Bean”—is a family favorite on the Chicago Food & Bike Tour. Ride into Millennium Park and watch kids light up as they see their reflections ripple across the mirrored surface with the skyline wrapped around them. Step underneath and look up—the distorted reflections create a funhouse effect that’s pure magic.

On this playful Bicycle Tour in Chicago, wide downtown paths make it easy for families to ride safely while guides share fun, bite-sized stories about how this iconic sculpture became a symbol of the city.

Among the most unforgettable Kid-Friendly Things to do in Chicago, experiencing Cloud Gate by bike—paired with classic Chicago eats—turns sightseeing into interactive family fun.

• Crown Fountain - Crown Fountain is pure fun for families on the Chicago Food & Bike Tour. Ride into Millennium Park and watch kids laugh as giant video faces “spit” water into the shallow reflecting pool. The faces are real Chicagoans—making this interactive artwork a celebration of the city’s people.

On this lively Bicycle Tour in Chicago, smooth downtown paths and open plazas make riding easy while guides share playful stories that keep everyone engaged.

Among the most refreshing Kid-Friendly Things to do in Chicago, splashing at Crown Fountain—then refueling with classic Chicago favorites—creates the perfect mix of art, movement, and delicious family adventure.

• Jay Pritzker Pavilion - Jay Pritzker Pavilion adds a wow factor to the Chicago Food & Bike Tour. Families ride into Millennium Park and see Frank Gehry’s sweeping steel design rise like a giant sculpture over the lawn. The overhead trellis isn’t just art—it’s engineered to deliver concert-quality sound across the entire park.

On this engaging Bicycle Tour in Chicago, kids love the open green space while guides share fun stories about summer concerts and city celebrations held right here.

Among the most inspiring Kid-Friendly Things to do in Chicago, experiencing Pritzker Pavilion by bike—paired with classic Chicago eats—blends architecture, music, and movement into one unforgettable family adventure.

• Tour guide
• Comfort bicycle
• Lunch
• Helmet

• $10 per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal)
• Alcoholic beverages

This Chicago Food & Bike tour, organized by Bobby’s Bike Hike, is ideal for the whole family. Their food tours have been recognized as Top 10 in America by USA Today and Top 20 globally by Tripadvisor in the past year. Chicago offers an easy biking experience with its extensive bike trails, flat terrain, and convenient connections between attractions. Participants will enjoy sampling Chicago’s famous and unique foods, including deep dish pizza, an authentic Chicago hot dog, and a delightful dessert. The tour also provides insights into the history of these foods while exploring some of Chicago’s most popular downtown areas, such as the Gold Coast, Chicago Riverwalk, Millennium Park, Buckingham Fountain, Museum Campus, Navy Pier, and the Lakefront. Whether during the day or at night, participants will enjoy stunning skyline views and the city’s lively atmosphere. Vegetarian options are available. Bikes, helmets, and all child equipment are included in this exciting bicycle tour of Chicago.

• If you have dietary restrictions, please add a note in the special requirements section when booking, and contact us after booking to confirm they can accommodate.
• Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
• VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
• TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
• Our Family-Friendly Chicago Food & Bike Tour groups have exclusive VIP access to locations we visit.
• Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
• Minimum numbers apply for the Kid-Friendly Chicago Food & Bike Tour. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
• Please note: children must be strong, capable riders and be able to bike for 9 miles. There are frequent stops for rest
• All Equipment included (bicycles, helmets, child equipment) in the Family Friendly Chicago Food & Bike Tour.

For a full refund, cancel at least 24 hours before the scheduled departure time.