Chicago Classic Food Walking Tour - 5 Tastings & Free Bike or Kayak Rental

Enjoy a hearty meal
of 5 Chicago classics

On this 3-hour guided walking tour, stroll through downtown at a relaxed pace and taste Chicago’s signature foods at 5 local restaurants. Choose between a noon tour and an evening tour; the tastings are generous enough to replace lunch or dinner. Your local guide shares stories about the food, the city and the people who shaped Chicago’s heritage.

From deep-dish pizza to Garrett popcorn,
taste Chicago’s icons

Taste deep-dish pizza with a buttery crust and rich tomato sauce, a Chicago-style hot dog piled high with toppings (never ketchup), and an Italian beef sandwich dipped in au jus and topped with spicy giardiniera. For dessert, the day tour serves the original-recipe brownie born in Chicago, while the evening tour serves warm churros (winter) or handmade gelato (summer). You will also sample Garrett Chicago Mix popcorn, a blend of sweet caramel and savory cheddar.

At check-in, you can add a pairing upgrade with 3 local craft beers, paid on site.

Walk past Chicago landmarks
like Millennium Park and the Mag Mile

The day tour visits the Magnificent Mile, the Chicago Riverwalk, the Chicago Theatre, Millennium Park, Cloud Gate (The Bean) and the Loop. The evening tour follows a slightly different route, stopping at the Mag Mile, the beautifully lit historic Water Tower, the Wrigley Building and the towering Holy Name Cathedral.

After the tour, keep exploring
with a free bike or kayak

Your ticket includes a free 2-hour bike or kayak rental. Ride a comfortable hybrid bike along the 20-mile Lakefront Trail, or paddle along the calm waters of Lake Michigan from Ohio Street Beach. Bikes are available year-round at the Bobby’s Bike Hike flagship location downtown (540 N. Lake Shore Drive).

※ The free rental can be used within 3 days after the tour.
※ Kayak rentals (550 E. Grand Avenue) are available only in the summer season when weather permits, and rentals are not available on Saturdays between Memorial Day and Labor Day.
※ The tasting menu is subject to change, and the tour runs rain or shine.