Loading Events
  • A bike tour riding past Chicago landmarks
  • Hot Italian Beef Sandwich on Chicago Food Tour
  • A Chicago bike tour in front of Buckingham Fountain
  • A Chicago style hot dog found on our food tours of Chicago
  • A Chicago Bike tour on the lakefront trail

Family-Friendly Tour of Chicago

Food & Bike Tour with Top Chicago Attractions

This could very well be the best family bike tour and food 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. While we love our walking and food tours to get into the nooks and crannies of the City, a bicycle allows us the freedom to explore so many parts of the City and sample delicious treats as we go. 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 offer a VIP craft beer upgrade on this tour, so that you can really get into that vacay mode! 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. Consider a VIP upgrade to enjoy a locally crafted beer pairing at three of the food stops. 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.

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.

What To Expect

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.

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.

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.

Deep-dish pizza is one of Chicago’s most famous recipes and lures pizza enthusiasts from all over the world. Learn the history of this epic pie and taste some of the best for yourself!

The Gold Coast neighborhood is known for its leafy upscale real estate, as well as its high-end dining and shopping. Check out this area and see the historic Gibson’s steakhouse, the original Playboy mansion, and the home of former Chicago bull, Dwyane Wade.

Located at the northwest corner of larger Grant Park, Millennium Park is home to Chicago’s most beloved works of public art, including Cloud Gate, The Crown Fountain, and the Pritzker Pavilion.

Gelato, is a delicious frozen dessert of Italian origin.

Marvel at the breathtaking design and natural beauty of the brand new Chicago Riverwalk.

When the Buckingham Fountain was built in 1927, it was the largest fountain in the world. Now the centerpiece of Chicago’s famous Grant Park, the fountain attracts crowds from all over the world to see its stunning light and water shows.

The Chicago-style hot dog is unlike any sausage creation you’ve had before—all beef frank, mustard, tomato, pickle, relish, onion, sport pepper, celery salt… But never ketchup! Have one and change the way you eat this ballpark favorite.

Chicago is making a name for itself as an American craft beer capital. We’re home to some of America’s favorite breweries, with new microbreweries appearing every year. Taste some of the most refined and refreshing pours as you learn about Chicago’s rich brewing history. Guests who are over 21 can add-on the VIP Craft Beer Package for only $19.75, which includes three 9oz pours of our favorite local brews.

The 18-mile Lakefront Trail has been contributing to Chicago’s cycle success since 1963. The paved path provides walkers, runners, and bicyclists with a safe and fun way to travel along Lake Michigan, for both recreation and commuting.

On summer weekends, Oak Street Beach is packed with the blankets and swim gear of up to 300,000 Chicagoans. Pop-up bars, volleyball nets, and easy access to downtown make this one of Chicago’s finest sandy spots.

Head Off on Chicago’s Family Food & Bike Tour

Is your mouth watering at the thought of trying all these incredible bites? We promise you will love this Chicago food and bike tour. It’s the best food tour of Chicago as well as the most unique since you bike to each location. Here are a few other excellent reasons to sign up for our day or evening tour:

  • You don’t have to be an expert biker to go: As long as you can ride a bike at a moderate pace, you can keep up with our tour.
  • You will learn something: Even Chicago residents often sign up for our tours because they want to know more about the place they call home.
  • You become part of the action: If you like to be active and engaged when touring a city, a bike tour is a perfect fit for your personality.

Plus, when you go on a tour with us, you get the opportunity to sample not just Chicago’s best food, but also it’s most desirable. If you try to get into these restaurants yourself, you may face a wait. On our tour, not only do you get to sample the food, but you may even get some off-menu items the chef decides to toss in there for fun. If you love food, that’s an opportunity you cannot pass up.

We love giving tours because it’s fun and because people really enjoy them. We think you will, too. Contact us today to book your family-friendly food tour of Chicago, by bike, and get ready to have one spectacular time on one of the best Chicago food tours.

Our Vendors

Lou Malnati’s Pizzeria has been a Chicagoland favorite since 1971, and was voted Best Pizza by Chicago Magazine’s Readers Choice in 2017.

Located directly below the world-famous “Cloud Gate,” Park Grill serves upscale American food and delicious beverages to Millennium Park visitors every day of the week. Enjoy a cozy of view of the McCormick Ice Rink skaters in the winter, and vibrant patio people-watching in the summer!

Located in the heart of the Chicago Riverwalk, Chicago Kernel serves up gourmet Chicago-mix popcorn – setting higher standards for taste, quality and customer service. Locals often refer to Chicago Kernel as “The City’s Best Kept Secret.”

Specializing in gelato and Italian beef, Bongiorno’s is a family-run business and takes pride in providing you with the best home-cooked Italian food and service in Chicago. Their many awards from the Hungry Hound, Chicago Magazine, and TripAdvisor speak well for their work.

Take Chicago’s Ultimate Food Tour by Bike

This bike-friendly city has loads for visitors to explore, and you’ll hit it all during the best family tour of Chicago, by bike! You learn the history of the area while also indulging your appetite. When you finish the tour, you will feel like you belong in the city. Other benefits of heading out with us include:

  • Getting fresh air on your vacation or staycation
  • Seeing parts of downtown you won’t find on other tours — places the natives also enjoy
  • Being amused for hours by our friendly guides and fun fellow bikers
  • Working off all the pizza, hot dogs and dessert you consume as you pedal around the city

Plus, Bobby’s Ultimate Chicago Food Tour by bike is so much more than just your average family food tour! We provide a chance to experience all of Chicago’s top food groups!

A Chicago style hot dog on a food tour of ChicagoGroup on Bike Tour of Chicago
Cloud Gate, or The Bean, in Millenium Park of ChicagoA cheesy slice of Chicago style deep dish pizza being served.
The Chicago theater marquee.A tour group sampling classic Chicago fare at a table during a Chicago food tour.
Palmer House Brownie on Chicago Food TourA view of boats and the Chicago riverwalk
  • Excellent overview of the Chicago downtown and lakefront area. Biking was fun, got to see and learn a lot on out short visit to Chicago. Tour guides paul and gave were excellent. Food was good, wish it was spread out a bit more.

  • We took our family of six to see and taste the highlights of Chicago. They had comfortable bikes for all sizes, even a trailer for our youngest. The food and beer was excellent with soda and cupcake stops for the kids to enjoy as well. Tough to keep up against... read more


Chicago Family Food & Bike Tour (with Top Attractions)

Duration: 4 hours
Length: 9mi / 14km
Level: Easy
Schedule: 11:00am & 4:30pm Daily
Age: 1+

(Discount Online Rate includes Bike, Food & Water)

Price: Fri-Sun Mon-Thurs
Adults(Ages: 12+) $74.99 $69.99
Youth (Ages 4-11) $64.99 $59.99
Infant(under 4 – if no extra food required) $10.99 $9.99
Electric Bike Upgrade $19.99
VIP Craft Beer Upgrade $19.99

Reserve Now
Private Tour
Get map to starting location

More Tours