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  • Beer and food from Tlayuda Cruz Blanca Restaurant in Chicago
  • group of people riding bikes along a street on Bobby's Bike Hike Chicago Bike & Food Tour Neighborhoods
  • bike tour group enjoy food and drinks
  • Fulton Market District entrance sign
  • Tour group showing off their muscles outside of Bucktown Pub beer garden
  • bike tour group with the downtown chicago skyline in the background

Chicago Westside Food Tour

Westside Foodie Bike Tour

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. Consider a VIP upgrade to include alcohol/beer pairings.

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.

What To Bring

  • Please bring an ID
  • Please bring a bottle of water. A few restaurants will serve water, but not all of them. So it’s highly recommended to bring a bottle of water.
  • Wear comfortable clothing/shoes
  • Face masks required at some restaurant venues

What’s Included

  • Tour prices include all food samples. *VIP Alcohol Pairing Upgrade at $19.99
  • Three craft beers with the VIP Alcohol Pairing Upgrade
  • Storied history of Chicago’s classic dishes and the establishments that created them
  • Informative bike tour of Chicago’s west side neighborhoods
  • Additional costs might be incurred for restricted diets or changes to menu items.
  • Please arrive 15 minutes before scheduled tour time!
  • Tours run snow, rain, or shine!

Departure Location

The Chicago River is the only river in the world that flows away from its mouth, and the reason for Chicago’s entire history of trade and commerce.

For the first 100 years of Chicago’s history, Fulton Market was a center of meatpacking and produce distribution. Now the trendy neighborhood and its low-rise warehouse buildings is home to some of the Windy City’s most esteemed restaurants and corporate headquarters.

There are few things that Chicagoans love more than craft beer. Microbreweries and big name beer brands have found a home and a loyal audience here for generations.

In 2016, online real estate brokerage Redfin named Ukrainian Village “the hottest neighborhood in the country” due to booming real estate prices and boasts an abundance of restaurants serving Eastern European fare.

Wicker Park is Chicago’s most famous arts district, home to more bookstores, record shops, and coffee houses per capita than any other neighborhood in Chicago.

The 606 Trail is a converted elevated freight line that now serves as a winding 2.7-mile bike and walking path on Chicago’s west side.

Old Town is one of Chicago’s most historic North Side neighborhoods. Beloved by beatniks in the 1950s and 60s, and hippies in the 70s, Old Town is now a quiet, tree-line arts district.

Drinking chocolate, also known as “sipping chocolate,” is a rich treat made by melting small bits of fine chocolate and blending with milk or cream.

The Lakefront Trail has been connecting Chicago’s north and south side neighborhoods since 1963. It spans 18 miles of the beautiful Lake Michigan waterfront and has played a large role in connecting Chicago’s vibrant cycling community.

Our Restaurant Partners

Kuma’s Corner is a Chicago institution that has been ‘harshing your mellow’ since 2005. Kuma’s is known for three things — their love of heavy metal, promoting locally crafted beer, and creating the finest burgers available on this planet (or any other for that matter).  You will get to sample two out of three of these loves, and all three if you choose the VIP Alcohol Upgrade.

Kasia’s Deli has been a West Town institution since the 1980s and was chosen as one of Chicago’s favorite comfort foods by Chicago’s Best in 2017.

Recently awarded the title ’50 best Tacos in America’, Antique Taco is a combination of everything husband/wife owners Rick & Ashley Ortiz love: flavorful food, antique style, and the comfort of home.

Terry’s ToffeeHand-crafted. Family-owned. Elevated ingredients. Following a recipe passed down from Terry’s Grandmother McCall, they make artisanal toffee with the best ingredients we can source from our partners around the world.

Cocoa & Co is a gourmet chocolate cafe and coffee bar in the Old Town neighborhood, with a heavy focus on sustainability and terroir.

Westside Burger on Chicago Food TourFlat Iron Building near Wicker Park in Chicago
Carnitas Tacos on Chicago Food Tour with Bobby's Bike Hikedining room at Cruz Blanca in Chicago
Pierogis on Chicago Food Tour with Bobby's Bike HikeFulton Market District entrance sign
Chicago Pub Crawl Tourscraft beer flight
trip advisor review

What Our Customers Are Saying“The Westside Foodie tour took us to many neighborhoods we would not have stumbled upon on our own – all of which were extremely safe and welcoming to our group. All of the food is excellent quality. Would definitely recommend…”

– Joe D.   London, UK

5/5 (1 Review)

Westside Foodie Ride Bike Tour

Duration: 4 hours
Length: 12mi / 20km
Level: Easy/Moderate
Schedule: 12:30pm Fri-Sun
Age: 21+

(Discount Online Rate includes Bike and Food, VIP Drink optional)

Price: Fri-Sun Mon-Thurs
Adults (Ages 21+) $84.99 $79.99
VIP Alcohol Pairing Upgrade $19.99
Electric Bike Upgrade $29.99

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Private Tour