Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

Lincoln Park, Chicago



Make the most of your day in Chicago by sampling Chicago's iconic style foods, seeing top attractions with a local, expert guide. Includes a FREE 2 hr bike or kayak rental to explore even more.

Chicago Food Tour with Free Bike or Kayak Rental

This 5-hour guided walking tour in downtown Chicago suits food lovers and explorers seeking iconic local flavors and landmarks.

Highlights

  • Sample five iconic Chicago dishes, enough for a full meal
  • Taste deep-dish pizza, Chicago-style hot dog, Italian beef sandwich, original brownie, and Garrett’s popcorn
  • Local expert guides share Chicago’s culinary history and stories while walking
  • Visit Millennium Park, Riverwalk, Magnificent Mile, Chicago Theater, Cloud Gate, and other landmarks
  • Includes a free 2-hour bike or kayak rental to extend your Chicago adventure

Description

Experience Chicago’s food and landmarks on a 5-hour walking tour led by local experts. This tour features generous tastings of classic dishes: deep-dish pizza with buttery crust and cheese, Chicago-style hot dog with all the traditional toppings, Italian beef sandwich dipped in au jus with giardiniera or sweet peppers, and the city’s original recipe brownie. Evening tours include a seasonal dessert choice of warm churro or house-made gelato. An optional VIP craft beer pairing with three local beers is available for $19.99 at check-in.

Along the way, explore notable landmarks such as the Magnificent Mile, Wrigley Building, Chicago Theater, Millennium Park, the Art Institute, Chicago Riverwalk, and Cloud Gate (“The Bean”). In colder months, some routes use the Pedway underground system for warmth; warmer months keep the tour at street level.

The tour’s relaxed pace and engaging storytelling make it accessible for all fitness levels. After the tour, use your included free 2-hour bike or kayak rental within three days. Bike rentals start from Bobby’s Bike Hike at 540 N. Lake Shore Drive, allowing you to explore the 20-mile Lakefront Trail. Kayak rentals (June–September only) are available at Ohio Street Beach, 550 E. Grand Avenue, weather permitting. Note that rentals are unavailable on Saturdays between Memorial Day and Labor Day and cannot be refunded or exchanged.

Includes

  • Cultural walking and food tour with five tastings from local restaurants, sufficient for a full meal
  • Slice of deep-dish pizza with buttery crust and cheese
  • Chicago-style hot dog loaded with classic toppings
  • Italian beef sandwich dipped in au jus with spicy giardiniera or sweet peppers
  • Original recipe rich chocolate brownie made in Chicago
  • Famous Garrett’s Chicago Mix popcorn combining caramel and cheddar
  • Optional craft beer pairing upgrade with three local samples ($19.99 at check-in)
  • Guided by a certified local expert sharing Chicago’s food and culture
  • Visits to Millennium Park, Cloud Gate, Riverwalk, Loop, Chicago Theater, Magnificent Mile, Wrigley Building, Holy Name Cathedral, Buckingham Fountain, City Hall, Daley Plaza, and the Library
  • Bonus free 2-hour bike or kayak rental for lakefront exploration

Excludes

  • Optional craft beer pairing upgrade ($19.99 at check-in)
  • Gratuity (suggested $10 per person)

Important Information

  • Arrive 15 minutes early for check-in
  • Tour operates rain, snow, or shine
  • Walking pace is relaxed and suitable for all fitness levels
  • Tastings are generous, equivalent to a full lunch or dinner
  • Notify in advance of any dietary restrictions
  • A 15% cash tip for the guide is suggested; no ATM on site
  • Food samples include deep dish pizza, Chicago-style hot dog, Italian beef, original brownie, and Garrett’s popcorn (items subject to change)
  • Free 2-hour bike or kayak rental valid within three days of the tour, weather permitting
  • Bikes can be used to explore the 20-mile Lakefront Trail
  • Kayak rentals available June–September at Ohio Street Beach, 550 E. Grand Avenue
  • Bike rental location: Bobby’s Bike Hike, 540 N. Lake Shore Drive
  • Kayak rentals unavailable on Saturdays between Memorial Day and Labor Day

Cancellation Policy

Cancel up to 24 hours in advance for a full refund.

For best experience, wear comfortable walking shoes, dress for the weather, and plan to book in advance. Take advantage of the included bike or kayak rental to explore Chicago’s lakefront at your own pace after the tour.

Frequently Asked Questions

You'll sample five iconic Chicago dishes including deep-dish pizza, Chicago-style hot dog, Italian beef sandwich, original brownie, and Garrett’s popcorn.
The guided walking tour lasts approximately 5 hours in downtown Chicago.
Yes, the tour visits Millennium Park, Riverwalk, Magnificent Mile, Chicago Theater, Cloud Gate, and other key landmarks.
Yes, a free 2-hour bike or kayak rental is included to extend your Chicago exploration after the tour.
Yes, you can choose either a 2-hour bike rental or kayak rental following the food tour in Chicago.
Local expert guides lead the tour, sharing Chicago’s culinary history and stories throughout the route.
The tour begins in downtown Chicago; check the website for the specific meeting point and current hours.
The tour involves walking around downtown Chicago for about 5 hours, so a moderate level of fitness is recommended.
Booking in advance is suggested as availability can vary; check the website for current dates and times.
The tour is family-friendly but may be best suited for older children and adults due to the walking distance and food portions.

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