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

Introduction: Exploring Chicago in a Day

If you’re visiting Chicago and looking to get a well-rounded taste of the city’s famous sights and flavors, the Full Day Food Walking Tour offered by Bobby’s Bike Hike might just be your ideal choice. For $100 per person, this five-hour adventure combines a lively stroll through downtown landmarks with sampling Chicago’s beloved cuisine and offers a free 2-hour bike or kayak rental to extend your exploration afterward.

One of the things we love about this tour is how it balances top sights like Millennium Park, Michigan Avenue, and the Chicago Riverwalk with delicious food stops, giving you both visual and culinary treats in one seamless experience. Another highlight is the guidance from local experts who share stories about Chicago’s history and current vibe, making the tour more than just a food crawl — it’s an engaging city introduction.

A potential consideration is that the tour covers quite a bit in five hours, so it’s best suited for those comfortable with some walking and standing. Also, keep in mind that the free bike or kayak rental is weather-dependent and must be used within a few days of your tour, which is a flexible perk but requires some planning. This tour suits travelers eager to combine sightseeing, local food, and active exploration into a single, memorable day.

Key Points

• Balanced Itinerary: Combines iconic sights with local eats for a comprehensive Chicago experience.
• Authentic Food Tasting: Sample Chicago-style deep-dish pizza, hot dogs, Italian beef, and desserts.
• Expert Guide: Enjoy insightful commentary about Chicago’s history, culture, and current events.
• Bonus Rental: Free 2-hour bike or kayak rental enhances your day, perfect for exploring more on your own.
• Accessibility: Designed to be leisurely and accessible for all fitness levels.
• Value & Awards: Recognized as one of the top food tours in the US and the world, offering excellent value.

You can check availability for your dates here:

The Full Experience: What You Can Expect

The Itinerary Breakdown

This tour takes you through Chicago’s most iconic landmarks — Millennium Park, with its famous Cloud Gate (the “Bean”), the bustling Michigan Avenue’s Magnificent Mile, the historic Chicago Theatre, and the lively Chicago Riverwalk. The guide, whose expertise we appreciate, shares stories and insights into the city’s development, architecture, and current scene.

As you meander through downtown, you’ll stop at several carefully chosen venues to sample signature Chicago foods. These include deep-dish pizza, a staple that truly defines the city’s culinary identity. You’ll get to taste a Chicago-style hot dog with all the fixings, a must-try for any visitor, and an Italian beef sandwich, another local favorite. And don’t forget the original recipe brownie — a sweet finish that pairs well with the tour’s savory flavors.

Authentic Food Stops and Tasting

The food stops are thoughtfully curated to give you a true taste of Chicago’s diverse culinary heritage. We loved the way each sample was part of a larger story — not just a bite but a glimpse into local traditions. One reviewer noted, “We had a terrific time exploring the food and city with an excellent guide,” highlighting how knowledgeable guides elevate the experience.

While the tour includes all food samples, there’s an optional VIP craft beer pairing for an additional $19.99. While not included in the base price, it’s a fun way to add a local brews experience, especially if you’re a beer enthusiast (note: over 21). During the stops, guides are attentive, ensuring everyone gets their fill and learns about each dish’s history.

Sightseeing & Commentary

Beyond food, you’ll marvel at the Chicago skyline, the Wrigley Building, and the Art Institute. The guide’s commentary enriches your understanding, blending historical tidbits with contemporary insights. We appreciated how they made the city’s stories come alive, making this more than just a walk and taste.

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The Bonus: Bike or Kayak Rental

After soaking in the sights and flavors, your ticket grants you a free 2-hour bike or kayak rental—a generous perk to extend your day. Bikes can be used along the 20-mile Lakefront Trail, giving you panoramic views of Lake Michigan and the city skyline. Kayaking from Ohio Street Beach offers a serene perspective of the city from the water, ideal from June to September.

The rental arrangements are straightforward: bikes are at Bobbys Bike Hike headquarters, and kayaks are at Ohio Street Beach. Conditions vary with weather, so it’s wise to plan your rental accordingly. Keep in mind, rentals are subject to weather restrictions and are not available during certain periods, like Saturday rentals between Memorial Day and Labor Day.

Practical Considerations for Travelers

• Duration & Group Size: The five-hour guided walk is leisurely enough for most fitness levels, with plenty of stops for food and photos. The group tends to be small enough for personal attention but large enough to enjoy a lively atmosphere.
• Cost & Value: At $100, the tour delivers a lot of value — multiple signature foods, sightseeing, expert commentary, and a bonus rental. Considering the awards and recognition it has received (Top 10 in America, Top 20 in the World), it’s a solid choice for those wanting an all-in-one city experience.
• Accessibility: The tour is wheelchair accessible, making it inclusive for many visitors.
• What to Bring: Comfortable shoes, a camera, and a reusable water bottle are recommended. Weather can vary, so dress accordingly.
• Tips & Extras: While gratuities aren’t included, tipping guides for good service is customary. The optional VIP craft beer upgrade is worth considering if you enjoy local brews.

Authentic Feedback from Travelers

One traveler from the US shared, “We had a terrific time exploring the food and city with an excellent guide,” confirming the tour’s quality. Conversely, a UK visitor expressed some disappointment, citing that their experience was modified and that the food portions and beer options didn’t quite meet expectations. This highlights that experiences can vary, especially with changes to the original plan.

A positive review highlighted the stunning views and safe, comfortable bike ride, noting, “There were no steep hills and the guide made sure the ride was safe and comfortable for everyone.” This reassures potential riders that the biking component is accessible even for those less confident on two wheels.

Why This Tour Matters

In the end, this tour offers a comprehensive taste of Chicago — from its famous landmarks to its iconic foods — all under the guidance of local experts. It’s perfect for travelers who want a structured yet flexible way to see the city, try its signature dishes, and enjoy some active fun afterward.

The free bike or kayak rental adds real value, making it an excellent choice for those wanting to extend their Chicago adventure without extra cost. Whether you’re a first-time visitor looking for an immersive overview or someone wanting to indulge in Chicago’s flavors and sights in a single day, this tour balances fun, education, and taste brilliantly.

Who Will Love This Tour?

If you enjoy guided walks that combine sightseeing and food tasting, you’ll find this tour engaging and satisfying. It’s especially suited for travelers who appreciate local insights and want to see top Chicago landmarks while sampling delicious regional dishes. The active component makes it ideal for those who like to combine culture with a bit of exercise, and the flexible rental option caters to those wanting to explore even more on their own.

However, if you prefer a more relaxed, less structured experience or have specific dietary restrictions, you might want to consider other options. Still, for most visitors wanting a lively, authentic, and varied introduction to Chicago, this tour hits the mark.

FAQ About the Chicago Full Day Food Walking Tour

Is this tour suitable for all fitness levels?
Yes, it’s designed to be leisurely and accessible, with plenty of stops and mostly flat walking. The bike portion is also suitable for most skill levels.

How long is the walking portion?
The guided tour lasts around five hours, including food tastings and sightseeing.

What foods will I sample?
Expect classic Chicago-style deep-dish pizza, hot dogs with all the toppings, Italian beef sandwiches, and a brownie. Optional craft beer pairing is available.

Can I upgrade to include craft beer?
Yes, there’s an option to add a VIP craft beer sample for about $19.99, available upon arrival.

Where do the bike and kayak rentals take place?
Bikes are at Bobbys Bike Hike headquarters on Lake Shore Drive; kayaks are at Ohio Street Beach. Both are within walking distance from the tour meeting point.

Are the tours wheelchair accessible?
Yes, the experience is wheelchair accessible.

What should I bring?
Comfortable shoes, a camera, and a water bottle are recommended. Weather-dependent, so check the forecast.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is there a guide included?
Yes, a local expert guides you through the sights and shares stories about Chicago’s history and culture.

When can I use my free rental?
The bike or kayak can be used within about three days of your tour date, with specific locations and times depending on weather and season.

To sum it up, this Chicago food and sightseeing tour offers excellent value for travelers eager to experience both the city’s landmarks and its culinary delights in one well-organized, engaging day. Its mix of guided exploration, tasty samples, and active options makes it a versatile choice for a wide range of visitors. Whether you’re in town for a short visit or simply want a lively introduction to Chicago, this tour is worth considering.

You can check availability for your dates here: