Chicago: Guided Food Tour + Bike or Kayak Rental

Chicago: Guided Food Tour + Bike or Kayak Rental

This Chicago guided food tour combines the city's legendary cuisine with active exploration options. You'll walk through downtown Chicago sampling four signature dishes whilst learning about the city's history and architecture. The tour includes a complimentary bike or kayak rental to use within three days, giving you two different ways to experience the Windy City.

Your guide leads you through the heart of Chicago, stopping at carefully selected spots to try deep-dish pizza, Italian beef sandwiches, Chicago-style hot dogs, and dessert. Between tastings, you'll walk along Michigan Avenue, the Chicago Riverwalk, and past landmarks including Millennium Park's Cloud Gate sculpture, the Chicago Theatre, and State Street. The tour covers both food history and architectural insights as you move through different neighbourhoods.

After your walking tour ends, you can choose between cycling the Lakefront Trail with skyline and Lake Michigan views, or paddling a kayak from Ohio Street Beach for a water-level perspective of the city. Both rentals offer flexible timing so you can explore at your own pace on a separate day.

What is Included

• Guided walking food tour with local guide
• Four food tastings: deep-dish pizza, Italian beef, Chicago-style hot dog, and dessert
• Complimentary bike rental (valid for 3 days after tour)
• Complimentary kayak rental alternative (valid for 3 days after tour)
• Optional VIP craft beer upgrade available (3 local brewery tastings)

Good to Know

The walking tour duration varies but expect around 2-3 hours moving between food stops and sights. You must arrive 15 minutes before your scheduled start time at the designated meeting point. Bring comfortable walking shoes as the tour is not wheelchair accessible.

Your bike or kayak rental must be redeemed within 3 days of your tour date. Bring a valid photo ID for the rental redemption. Instructions for claiming your rental will be provided at the end of your walking tour. Vegetarian options may be limited at some food stops due to Chicago's meat-heavy signature dishes.

For more Chicago experiences, consider the Chicago architecture boat tour to see the city's famous skyline from the water, or explore other local favourites with a Chicago craft beer walking tour through different neighbourhoods.