Chicago: Classic Food Walking Tour with Bike or Kayak Rental

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Discover Chicago’s famous classic foods like pizza, hot dogs, and brownies on a guided food tour. Visit city highlights like Millennium Park and Chicago Riverwalk, and enjoy a bike or kayak rental.


  • Visit some of Chicago's most beautiful attractions, including Millennium Park
  • Sample Chicago-style deep-dish pizza and hot dogs
  • Enjoy a classic Chicago Italian Beef sandwich and original recipe brownie
  • Enjoy the stories of a local, professional guide
  • FREE 2 hour bike or kayak rental (to be used within 3 days of your tour booking)


Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 3-hour guided walk, you'll get to taste the foods Chicago is best known for inventing and doing right. Enjoy deep-dish pizza, the original recipe brownie, a Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional $19.99/person fee for 3 craft beer sample pairings (offered upon arrival). Leave the planning to the local experts. Bobby’s Bike Hike was awarded the following three awards just this year: “Top 10 Food Tours in America” by USA Today, “Top 20 Food Tours in the World” by TA, and “Top 15 Vacation Ideas in USA” by Entrepreneur Magazine. Seize the opportunity for the ultimate Chicago fusion of flavors and sights in a single, unforgettable day! Along the way, you’ll see some of Chicago's most iconic spots including the Magnificent Mile, the Wrigley Building, Chicago Threatre, Millennium Park, the Chicago Riverwalk, the Art Institute, and the world famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels. As a delightful bonus, enjoy a FREE 2-hour Bike or Kayak rental within +/-3 days of your tour date. Glide along Chicago's world-famous 20-mile Lakefront Trail on a comfortable hybrid bike, or paddle the serene waters of Lake Michigan at Ohio Street Beach, a picturesque gem in the heart of Chicago. FREE 2 HOUR BIKE or KAYAK RENTAL INFO: As an additional perk for booking this particular tour, you will get a FREE 2-hour bike or kayak rental (to be used within (+/-) 3 days of your tour booking. Terms below: To be used within +/- 3 days of your tour booking. Bike rentals take place at Bobby’s Bike Hike World Headquarters, 540 N. Lake Shore Drive, Chicago, IL60611. Bike shop is open year-round (excluding Thanksgiving & Christmas). Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611. Kayak shop open mid-May to mid-October, weather dependent. Offer excludes Saturday Bike/Kayak rentals between Memorial Day (end of May) Weekend to Labor Day (early September). Kayaking only available from June-September) No discounts for not using this activity or issues due to weather restrictions.


Walking tour Guide Food tastings Bike or kayak rental

Important Information

  • Bring a camera and then enter your best picture in a photo contest on Facebook A 15 % to 20 % tip is suggested for the guide. Please bring cash, there is no ATM on-site Tours run snow, rain or shine
  • As part of this experience, enjoy a Free 2-hour Bike Rental or Kayak Rental (weather permitting) to punctuate your full day Chicago Experience. Bikes can be used to explore the 20-mile Lakefront Trail. Kayaks from Chicago’s most photo-worthy beach, Ohio Street Beach (June-September).
  • Bike rentals take place at Bobby’s Bike Hike, 540 N. Lake Shore Drive, Chicago, IL60611 Kayak rentals take place at Ohio Street Beach, Bobby’s Kayak, 550 E. Grand Avenue, Chicago, IL 60611

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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