Chicago: Classic Food & Walking Tour with Free Bike or Kayak｜United States

Voted Top 10 Food Tours in America by USA Today, Top 20 Food Tours in the World by KKday, and one of the Top 15 Experiences in the USA by Yelp, this award-winning Chicago Food Tour offers a flavorful way to explore the best of the city.

On this 3-hour guided walking tour, you’ll experience an authentic slice of Chicago through its most iconic foods while enjoying a laid-back stroll through downtown. You’ll taste the dishes that made the city famous: a slice of deep-dish pizza with its rich tomato sauce and buttery crust, a fully loaded Chicago-style hot dog piled high with toppings (and absolutely no ketchup), a juicy Italian beef sandwich dipped in savory au jus and served with spicy giardiniera, and the original recipe brownie, a decadent dessert born right here in Chicago. Guests on the evening tour will enjoy a handcrafted gelato instead of the brownie, a cool and creamy treat from one of the city’s best dessert spots. For those looking to elevate their experience, an optional craft beer pairing is available at check-in for an additional $19.99 fee and includes three tastings of locally brewed favorites.

As you enjoy each bite, your guide will lead you past some of the most iconic Chicago attractions, sharing the stories behind the food, the city, and the people who built its legacy. On daytime tours, you’ll stop at Millennium Park, Cloud Gate (known as “The Bean”), the Chicago Riverwalk, the Art Institute, the Magnificent Mile, the Wrigley Building, and the historic Chicago Theater. Evening tours offer a slightly different route, with stops including the beautifully lit Historic Water Tower and the towering Holy Name Cathedral. Whether day or night, you’ll walk away with incredible photos, fun facts, and a newfound love for Chicago’s rich food culture.

Your ticket also includes a free two-hour bike or kayak rental, valid within three days before or after your tour. You can use this to ride the scenic 20-mile Lakefront Trail on a comfortable hybrid bike or paddle along the peaceful waters of Lake Michigan from Ohio Street Beach. Bike rentals are available year-round at Bobby’s Bike Hike downtown headquarters, while kayak rentals are offered seasonally from May to October, weather permitting. Please note that rentals are not available on Saturdays between Memorial Day and Labor Day.

Whether you're a first-time visitor or a lifelong local, this tour offers one of the most fun and flavorful things to do in Chicago. With generous tastings, fascinating stories, and access to top attractions, it's the perfect way to spend a day in one of America’s greatest food cities. Bobby’s Bike, Hike & Food Tours is Chicago’s only locally owned and operated food tour company. Our guides have lived the stories, know the chefs personally, and share a passion for showcasing the real flavors and culture of their hometown. Join the locals who love to share their city, and experience Chicago like never before—through its food, its stories, & its streets.