Chicago: Classic Food and Walking Tour with Free Bike/Kayak

Chicago Food Tour: Iconic Local Eats and City Sights

This 3-hour guided walking tour in downtown Chicago features five iconic local foods and visits top city attractions, suitable for food lovers and first-time visitors.

Highlights

• Savor five iconic Chicago bites—enough food 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 food history and city stories
• Walk to Millennium Park, Chicago Riverwalk, Magnificent Mile, Chicago Theater, and Cloud Gate (morning tour)
• Includes a free two-hour bike or kayak rental to extend your Chicago adventure

Description

Recognized among the top food tours in America and the world, this award-winning Chicago Food Tour offers an authentic taste of the city through its most famous dishes. On a relaxed 3-hour walk, you’ll sample deep-dish pizza with rich tomato sauce and buttery crust, a fully loaded Chicago-style hot dog (no ketchup), a juicy Italian beef sandwich dipped in au jus with spicy giardiniera, and the original Chicago brownie recipe. Evening tours substitute the brownie with a handcrafted gelato from one of the city’s standout dessert locations. An optional craft beer pairing, available at check-in for $19.99, includes three local beer tastings.

Guides lead you past iconic Chicago landmarks while sharing stories about the food, city, and its people. Daytime tours stop at Millennium Park, Cloud Gate (“The Bean”), Chicago Riverwalk, Art Institute, Magnificent Mile, Wrigley Building, and the Chicago Theater. Evening tours include the illuminated Historic Water Tower and Holy Name Cathedral. You’ll capture memorable photos, learn local history, and appreciate Chicago’s food culture.

Your ticket includes a free two-hour bike or kayak rental valid for three days before or after your tour. Bikes allow exploration of the 20-mile Lakefront Trail from Bobby’s Bike Hike downtown headquarters. Kayak rentals, offered May to October from Ohio Street Beach, provide a scenic paddle on Lake Michigan. Note that rentals are not available on Saturdays between Memorial Day and Labor Day.

This tour suits both visitors and locals seeking an engaging way to experience Chicago’s food and stories. Guides are local experts passionate about the city’s culinary scene and history. Booking in advance is recommended; dress for walking and check seasonal availability for kayak rentals.

Includes

• Cultural walking and food tour with five tastings from top local restaurants—enough for a full meal
• Slice of legendary deep dish pizza with buttery crust and gooey cheese
• Classic Chicago-style hot dog loaded with traditional toppings
• Savory Italian beef sandwich dipped in au jus with spicy giardiniera or sweet peppers
• Original recipe brownie on daytime tours; warm churro (winter) or house-made gelato (summer) on evening tours
• Famous Garrett’s Chicago Mix popcorn, a sweet and salty blend of caramel and cheddar
• Optional craft beer pairing upgrade: 3 local beer samples for $19.99 at check-in
• Certified local expert guides who share Chicago’s flavors and stories
• Day Tour stops: Millennium Park, Cloud Gate, Riverwalk, Loop, Chicago Theater, Magnificent Mile
• Evening Tour stops: Magnificent Mile, Historic Water Tower, Wrigley Building, Holy Name Cathedral
• Bonus: Free 2-hour bike or kayak rental to explore the lakefront

Excludes

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

Important Information

• Arrive 15 minutes early for check-in
• Tour operates rain or shine, snow included
• Relaxed walking pace, suitable for all fitness levels
• Tastings are generous, sufficient for a full lunch or dinner
• Notify in advance for dietary restrictions
• Suggested 15% cash tip for guides (no ATM on site)
• Taste samples include deep dish pizza, Chicago-style hot dog, Italian beef, original brownie (day), warm churro or gelato (evening), and Garrett’s Chicago Mix popcorn (items may vary)
• Free 2-hour bike or kayak rental valid within 3 days of the tour
• Bike rentals available year-round at Bobby’s Bike Hike, 540 N. Lake Shore Drive
• Kayak rentals seasonal (June–September) at Ohio Street Beach, 550 E. Grand Avenue
• Kayak rentals not available Saturdays between Memorial Day and Labor Day

Cancellation Policy

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