Chicago in a Day: Food & Walk Tour+Free Bike or Kayak Rental

Highlights

• Savor five iconic Chicago bites—enough food to satisfy a full hearty meal.
• Taste deep dish, hot dogs, Italian beef, brownie, and Garrett’s popcorn.
• Local expert guides share Chicago’s rich stories as we explore top sites on foot
• Stroll to Millennium Park, Riverwalk, Magnifecent Mile, Chicago Theater, Cloud Gate
• Includes FREE 2-hour bike or kayak rental to extend your Chicago adventure.

Description

Experience the perfect blend of flavor, history, and iconic landmarks with Bobby’s Bike, Hike & Food Tours, proudly named a Top 10 Food Tour in America by USA Today, one of the Top 20 Food Tours in the World by TripAdvisor, and one of the Top 15 Vacation Ideas in the USA by Yelp. This 5-hour walking adventure is one of the best things to do in Chicago, designed for food lovers and explorers who want to experience Chicago in a Day. Your ticket also includes a FREE 2-hour bike or kayak rental, so you can keep the adventure going after your tour.

As you explore downtown on foot, your local guide will introduce you to the bold flavors that define Chicago’s culinary heritage. Enjoy a slice of rich, cheesy deep-dish pizza, savor a fully loaded Chicago-style hot dog, bite into a juicy Italian beef sandwich topped with spicy giardiniera or sweet peppers, and indulge in the original recipe brownie—created right here in Chicago. Evening guests can enjoy a seasonal dessert of either a warm churro or house-made gelato. To elevate the experience, a VIP craft beer pairing is available at check-in for an additional upgrade.

Beyond the food, this immersive experience showcases some of the city’s most beloved landmarks. You'll stroll past the Magnificent Mile, take in the beauty of the Wrigley Building, admire the Chicago Theater, and explore Millennium Park, the Art Institute, the Chicago Riverwalk, and Cloud Gate, affectionately known as "The Bean." In colder months, part of the route may use the city’s underground Pedway system for warmth, while warmer seasons keep you immersed in the vibrant Loop at street level.

With its relaxed pace and engaging storytelling, this tour is accessible to all fitness levels and is one of the most enjoyable and enriching Chicago Food Tours available.

As a bonus, your ticket includes a FREE 2-hour bike or kayak rental, valid within three days of your tour. Ride along the stunning 20-mile Lakefront Trail from Bobby’s Bike Hike downtown headquarters at 540 N. Lake Shore Drive, or paddle the peaceful waters of Lake Michigan from Chicago's most photo-worthy beach, Ohio Street Beach at 550 E. Grand Avenue (kayak rental available June–September, weather permitting). Please note: rentals are not available on Saturdays between Memorial Day and Labor Day and cannot be refunded or exchanged.

Whether you're a first-time visitor or a curious local, this experience delivers the sights, flavors, and spirit of Chicago in a Day—a truly unforgettable way to taste and explore the city.