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

Discover Chicago’s classic foods such as deep-dish pizza, hot dogs, Italian beef, and brownies on a 3-hour guided walking tour offered by Bobby’s Bike Hike. For $80 per person, this tour combines a taste of Chicago’s culinary treasures with visits to iconic sights like Millennium Park and the Chicago Riverwalk. An outstanding feature is the free 2-hour bike or kayak rental available within three days, giving ample opportunity to explore the Lakefront Trail or paddle around Ohio Street Beach. Perfect for those wanting an immersive day of food, culture, and sightseeing, this tour has earned a rating of 4.8 out of 5 from 140 reviews, thanks to its knowledgeable guides and generous servings.

While the tour accommodates a leisurely pace suitable for all fitness levels, it’s worth noting that the bike and kayak rentals are weather dependent and exclude Saturday rentals from Memorial Day to Labor Day. Still, this experience offers exceptional value, especially with the added perk of exploring Chicago’s scenery on your own afterward.

Key Points

• Price: $80 per person for a 3-hour tour combining food tasting and sightseeing
• Duration: 3 hours, usually available in the morning and evening
• Highlights: Chicago-style deep-dish pizza, hot dogs, Italian beef, brownies, and city landmarks
• Extra Perk: Free 2-hour bike or kayak rental within +/- 3 days of booking
• Guides: Knowledgeable, personable, with detailed stories behind each food and site
• Includes: Guided walk, food tastings, and rental equipment; drinks are available to purchase separately

You can check availability for your dates here:

Exploring Chicago’s Top Food Stops and Landmarks

Sampling Chicago’s Most Famous Foods

This tour shines in offering a taste of Chicago’s culinary inventions. You’ll get to try deep-dish pizza and Chicago-style hot dogs, two of the city’s most recognizable foods. The tour also features a classic Italian beef sandwich and an original recipe brownie, with daytime tours enjoying the brownie and evening tours offering hand-crafted gelato instead. These hearty servings ensure your stomach is satisfied and provide authentic local flavors.

Guided Stories from Local Experts

The guides lead with enthusiasm and detailed knowledge, sharing fascinating stories about each dish and Chicago’s food history. Guides like Julia, Jeff, and Gabe are praised for their personable nature and ability to make the tour engaging, whether explaining the origins of the foods or highlighting city landmarks. This storytelling makes the experience more than just food tasting—it becomes an insightful journey through Chicago’s cultural landscape.

Iconic Chicago Landmarks on Foot

While walking through downtown Chicago, the tour visits famous spots like Millennium Park, home to the Bean, the Magnificent Mile, the Wrigley Building, and the Chicago Theatre. The Chicago Riverwalk also features prominently, offering picturesque views and photo opportunities. For evening tours, stops include the Historic Chicago Water Tower and Holy Name Cathedral. The leisurely pace ensures all guests can comfortably enjoy the sights and stories along the way.

More Great Tours Nearby

The Unique Offer of Free Bike or Kayak Rental

A standout feature is the free 2-hour bike or kayak rental available within three days of the tour. Bikers can cruise along the 20-mile Lakefront Trail, enjoying Chicago’s lakeside scenery, while kayakers can paddle at Ohio Street Beach, a scenic spot on Lake Michigan. The bike rental takes place at Bobby’s Bike Hike headquarters on 540 N. Lake Shore Drive, open year-round except on major holidays. The kayak rental at 550 E. Grand Avenue is seasonal, from mid-May to October. This bonus encourages further exploration of Chicago’s vibrant waterfront.

Practical Details and Logistics

The meeting point varies depending on the selected option but is coordinated to ensure convenience. The tour includes a walking guide, food tastings, and rental gear, with no additional costs for the rental. Drinks are not included but can be purchased separately at each stop. The tour runs rain or shine, and wheelchair accessibility is available, making it suitable for most visitors.

The Value and Customer Satisfaction

Rated 4.8 out of 5 from 140 reviews, this tour consistently receives praise for its knowledgeable guides, generous food portions, and well-paced itinerary. Reviewers mention guides like Gabe, Julia, and Jeff as engaging and informative, making the experience memorable. Many appreciate the balance of food, sightseeing, and fun stories, with some noting the generous servings and the opportunity to explore Chicago’s scenic lakefront afterward.

Considerations and Limitations

Potential guests should plan for weather-dependent kayak rentals and note Saturday restrictions during peak summer months. The additional cost for craft beer pairings (around $19.99) offers a bonus for beer enthusiasts. Also, a tip of 15-20% for guides is customary, so bringing cash is recommended.

Why This Tour Works for Chicago Visitors

This food and sightseeing combo offers great value for those eager to sample Chicago’s most iconic dishes while exploring the city’s top attractions. The small group atmosphere and friendly guides ensure a personal experience, perfect for first-time visitors or locals looking for a fun way to rediscover their city.

The free bike or kayak rental is a superb addition, giving guests the chance to extend their day with self-guided adventures along Lake Michigan. Plus, the leisurely walking pace makes this accessible to most fitness levels, while the educational storytelling deepens the appreciation for Chicago’s culinary and architectural heritage.

In summary, this tour is ideal for food lovers, culture seekers, and outdoor explorers alike. It combines the best of Chicago’s flavors, sights, and scenery with an unbeatable bonus of rental equipment at no extra cost.

Frequently Asked Questions

What foods are included in the tour?
You’ll sample deep-dish pizza, hot dogs, Italian beef sandwiches, brownies (or gelato in the evening), and optional craft beer pairings.

How long is the bike or kayak rental?
The rental lasts 2 hours and can be used within three days of the tour. It takes place at Bobby’s Bike Hike headquarters and Ohio Street Beach for kayaking.

Is the tour accessible for all?
Yes, the tour is wheelchair accessible and designed with a leisurely pace suitable for most fitness levels.

Can I cancel or change my reservation?
Yes, full refunds are available if canceled up to 24 hours before the scheduled tour.

Are drinks included?
No, drinks are not included but are available for purchase at stops along the way.

What is the main highlight of this tour?
The combination of Chicago’s iconic foods, fascinating city sights, and the free outdoor rental experience makes this tour a well-rounded way to enjoy a day in Chicago.

You can check availability for your dates here: More Great Tours Nearby