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

Planning a trip to Chicago? If you’re looking for an experience that combines savoring iconic foods with exploring some of the city’s most famous sights, this tour might just be what you’re after. While we haven’t done it ourselves, we’ve looked into it carefully to give you a balanced sense of what to expect. It promises a smooth blend of delicious tasting stops, sightseeing highlights, and a bit of outdoor adventure afterward.

What caught our eye? First, the fact that it covers Chicago’s culinary staples — deep-dish pizza, hot dogs, Italian beef, and brownies — all in one go. Plus, the guided insights into Chicago’s attractions add a layer of local knowledge that’s hard to beat. We also love the complimentary 2-hour bike or kayak rental, giving you room to stretch your legs and enjoy the lakefront, which is a huge plus for combining food, culture, and outdoor fun.

However, one thing to keep in mind is that the price point is around $100 per person, which isn’t budget-friendly for everyone. It’s a decent value if you enjoy sampling multiple foods and want a guided tour with local insights, but if you’re on a tight budget or prefer independent wandering, this might feel a bit packaged.

This tour seems best suited for travelers who want a well-rounded day in Chicago—those who enjoy food, sightseeing, and outdoor activity—without the hassle of planning each detail. It’s a good fit whether you’re new to the city or just looking for a convenient way to hit the highlights.

Key Points

• Balanced experience with food tastings and sightseeing
• Expert local guide offering insights into Chicago’s history and current scene
• Includes a free outdoor activity (bike or kayak) to explore more of the city
• Accessible format suitable for most fitness levels
• Great for food lovers wanting a taste of Chicago’s iconic dishes
• Price reflects a comprehensive 5-hour experience with extras

You can check availability for your dates here:

What You Can Expect from the Tour

This five-hour adventure is carefully designed to give you a taste of Chicago’s culinary traditions and its most recognizable sights. Starting with a guided walk through downtown Chicago, you’ll visit landmarks like Millennium Park, Michigan Avenue, the Chicago Theatre, and the Chicago Riverwalk. The guide’s commentary isn’t just about food—it includes history and current events, making the experience educational as well as flavorful.

The Food

The star of the tour is, of course, the food. You’ll sample Chicago-style deep-dish pizza—a hearty, cheesy, buttery crust masterpiece—and a Chicago hot dog loaded with all the typical toppings. The tour also offers a classic Italian Beef Sandwich, renowned for its tender beef and flavorful broth, alongside a original recipe brownie that hits that sweet spot. If you opt for the VIP craft beer pairing (available on arrival), you’ll get three samples that complement the food, adding a fun adult twist.

Reviews highlight the food portion as generally satisfying, with some noting the stops are well-paced. One traveler remarked, “We had a terrific time exploring the food and city with an excellent guide,” which suggests most guests leave full and happy.

The Sightseeing

While the focus is on food, you won’t miss out on the sights. Your guide will point out Magnificent Mile, Wrigley Building, Chicago Theater, Millennium Park, and the Chicago Riverwalk, among others. The tour makes it easy to see Chicago’s highlights without feeling rushed, making it suitable for all ages and fitness levels.

The Outdoor Activity

Post-food, the fun continues with the FREE 2-hour bike or kayak rental, which you can use within three days of your tour. Bikes can be taken out on the famous 20-mile Lakefront Trail, perfect for a breezy ride along Lake Michigan with fantastic views. If you prefer water, kayaking at Ohio Street Beach offers a peaceful way to see Chicago from a different perspective—note that kayaking is seasonal (June-September) and weather-dependent.

This outdoor perk really adds to the value, especially because it’s free, and you get to extend your Chicago adventure beyond the guided tour.

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The Tour Logistics: Details That Matter

The tour is designed for a leisurely 5 hours, usually starting in the morning, giving you plenty of daylight to enjoy Chicago afterward. The group size isn’t specified but based on reviews, it’s probably moderate, enabling meaningful interaction without feeling crowded. The guide is described as knowledgeable and approachable, creating a lively and informative atmosphere.

The price of $100 per person seems fair, considering it includes all food samples, attractions, commentary, and the outdoor rental. Compared to booking each activity separately, it offers good value, especially for visitors eager to combine eating and sightseeing effortlessly.

What’s Included

• Expert, local guide providing insights beyond the basic tour
• All food samples at various stops
• Entry to attractions and commentary
• Free 2-hour bike or kayak rental

What’s Not Included

• Guide gratuity (a typical tip is appreciated)
• Optional VIP craft beer pairings, available at an extra cost
• Any personal expenses beyond what’s included

Meeting Point & Timing

Arrive 20 minutes early, look for a guide wearing a Bobby’s Bike Hike branded polo and holding a branded paddle. The tour runs in the morning, making it a great way to kick off a day of exploring Chicago.

Honest Feedback from Past Participants

While most reviews are glowing, a couple of comments offer valuable tips. One reviewer from the UK noted that their booking was moved to a different tour, and they found the food portions somewhat light for the $100 price, with a few small bites and a large beer that didn’t quite hit their expectations. The guide was described as new, which might affect the overall experience for some.

On the other hand, another traveler praised the guide D.K., mentioning the small group and the excellent views. They appreciated the safe, comfortable ride, reinforcing that the tour caters well to varying fitness levels.

This mix of feedback suggests that if you’re someone who appreciates engaging guides and generous tastings, you’ll likely be pleased. If you’re more particular about food portions or beer quality, it might be worth considering your expectations before booking.

Final Thoughts: Is This Tour for You?

If you’re after a convenient and comprehensive way to experience Chicago’s top sights along with its culinary icons, this tour offers a lot. The combination of guided sightseeing, food tasting, and outdoor activity makes it appealing for travelers who want variety in their day without the fuss of planning each piece.

It’s especially suited for first-time visitors who want to get the lay of the land and sample classics, or for those who enjoy trying local flavors in a social, guided setting. The free outdoor rental is a definite bonus, allowing you to extend your exploration on your own — whether biking along the lake or paddling in Lake Michigan.

That said, if you’re on a tight budget, prefer more food for your money, or are looking for a highly flexible or private experience, you might find this tour somewhat structured. Also, keep in mind that the food portions are described as satisfying but not overly generous, and the beer pairing is an optional upgrade.

This is a solid, enjoyable experience that balances food, sights, and outdoor fun. It’s an excellent way to see Chicago without overcommitting, leaving room to explore even more on your own afterward.

FAQs

Is this tour suitable for children? The tour is generally geared towards adults, especially with the optional craft beer pairing, which is for those 21 and over. The walking and outdoor activities are suitable for most ages, but check the specifics if traveling with little ones.

How long is the tour? The guided part lasts about 5 hours, usually in the morning, making it a good way to start your day.

Do I need to book in advance? Yes, it’s recommended, especially since you need to arrive early for check-in and the tour can fill up, as indicated by the booking process.

Can I use the free bike or kayak rental anytime? You can use it within three days of your booking, weather permitting. Biking is year-round; kayaking is seasonal (June-September).

What’s included in the price? All food samples, attractions, commentary, and the free outdoor rental are included. Tips and optional extras like craft beer are extra.

Is the outdoor activity strenuous? No, both biking and kayaking are suitable for most fitness levels, and the guide ensures a comfortable pace.

What should I bring? Comfortable shoes, a camera, and a reusable water bottle are all you need. Dress appropriately for the weather and walking.

In the end, if you’re eager to combine Chicago’s best eats with sightseeing and outdoor fun, this tour offers a well-rounded package. Just be prepared for some small bites and a possibly lively guide, but overall, it looks like a great way to spend a day exploring the Windy City.

You can check availability for your dates here: