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

Make the most of a single day in Chicago with this vibrant full-day food walking tour priced at $100 per person. Spanning approximately five hours, this experience combines famous city sights with Chicago’s beloved culinary staples, all led by an expert local guide. A unique feature of this tour is the FREE 2-hour bike or kayak rental that you can use within three days—a perfect way to extend your adventure along the Lakefront Trail or Lake Michigan.

This tour is especially appealing for visitors wanting a comprehensive taste of Chicago—from its iconic landmarks to its culinary treasures—without the hassle of planning. While the tour covers many highlights and includes delicious food samples, it’s worth noting that the food experience might feel somewhat brief for those seeking a full meal at each stop. This tour suits those who want a combination of sightseeing and food in a relaxed, guided setting.

Key Points

• Five-hour guided tour through downtown Chicago, focusing on food and city sights
• Includes food samples of Chicago-style deep-dish pizza, hot dogs, Italian beef, and brownies
• Led by an expert local guide providing commentary on history and current events
• Offers a FREE 2-hour bike or kayak rental to explore Chicago’s Lakefront within three days
• Tour costs $100 per person and is wheelchair accessible
• Optional VIP craft beer tasting available for an extra $19.99

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Chicago Landmarks: Millennium Park, Michigan Avenue, and the Chicago Theatre

The tour starts in downtown Chicago, where you’ll see the Magnificent Mile, Wrigley Building, and the Chicago Theatre. These landmarks are some of the city’s most recognizable features and set the scene for a day full of sights and stories. Your guide provides insights into both the historical significance and the current ambiance of these locations, helping you appreciate Chicago’s architectural beauty and vibrant culture.

Walking along Michigan Avenue, you’ll get a sense of Chicago’s bustling urban life. Observing the Millennium Park and the iconic Cloud Gate (the Bean) offers fantastic photo opportunities. Whether you’re a first-time visitor or returning, the guide’s commentary brings these places to life, making the sightseeing both informative and engaging.

Sampling Chicago’s Classic Foods: Deep-Dish Pizza, Hot Dogs, and Italian Beef

Food is at the heart of this tour, and you’ll get to taste some of Chicago’s most famous dishes. The experience includes deep-dish pizza, where you savor the city’s signature thick, cheesy, and hearty slice. Next, indulge in a Chicago hot dog loaded with all the traditional fixings, giving you a true taste of local street food.

A stop at a classic Italian Beef Sandwich shop allows you to sample the original recipe for this Chicago favorite. Plus, the tour features a delicious brownie, noted as a classic in Chicago’s culinary scene. For those interested in craft beers, an optional VIP pairing can be purchased upon arrival, offering three beer samples to complement your bites.

Engaging Commentary from an Expert Local Guide

Throughout the walk, the guide provides insights into Chicago’s history, culture, and current events. Based on recent reviews, guides like D.K. are praised for their storytelling skills and friendly approach. They make the city’s landmarks and food stops more meaningful by sharing background stories and interesting facts, enriching the overall experience.

The guide’s knowledge extends beyond food, offering context about Chicago’s architecture and neighborhood histories, which helps you connect what you see and taste in a deeper way. The commentary is suitable for all ages and fitness levels, ensuring everyone feels comfortable and engaged.

The Free Bike or Kayak Rental: Explore More of Chicago

A standout feature of this tour is the complimentary 2-hour rental of either a hybrid bike or a kayak, valid within three days of the tour. The bike rental takes place at Bobbys Bike Hike World Headquarters on North Lake Shore Drive, and lets you explore the famous 20-mile Lakefront Trail. This is an easy ride suited for all fitness levels, offering scenic views of the lake, parks, and city skyline.

Alternatively, the kayak rental at Ohio Street Beach is available from mid-May to mid-October, weather permitting. Paddling on Lake Michigan provides a peaceful vantage point to see the city’s skyline from a different perspective. It’s a relaxing way to extend your Chicago experience at your own pace.

Note that certain restrictions apply, such as no rentals on Saturdays from Memorial Day to Labor Day, and weather-dependent operation for kayaks.

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Practical Details: Meeting Point, Timing, and Accessibility

The tour departs from a conveniently located meeting point in downtown Chicago. It’s recommended to arrive 20 minutes early for check-in, where you’ll find your guide wearing a Bobbys Bike Hike branded polo. The tour operates mainly in the morning and has a 5-hour duration, making it easy to include in a full day of activities.

This tour is wheelchair accessible, and it’s advisable to wear comfortable shoes and bring a camera to capture the sights. A reusable water bottle is recommended to stay hydrated during the walk.

Value and Additional Options

For $100 per person, the tour offers an all-inclusive food experience, sightseeing, commentary, and the free bike or kayak rental—a combination that provides good value for a day of exploration. An optional VIP craft beer pairing is available at $19.99, allowing a tasting of three beers at certain stops.

While gratuities are not included, the tour’s awards—such as being listed among the Top 10 Food Tours in America by USA Today—highlight its reputation for quality and excellence.

Final Thoughts on the Chicago Food & Sightseeing Tour

This tour offers a well-rounded introduction to Chicago, combining famous landmarks with iconic foods. The presence of an expert guide ensures you’ll gain interesting insights while enjoying a relaxed pace suitable for all fitness levels. The inclusion of a free bike or kayak rental adds significant value, giving you a way to explore Chicago’s lakefront at your own speed.

However, those seeking a full meal experience at each stop might find the food sampling somewhat light. The tour is most suitable for visitors wanting a combination of sightseeing and quick bites, rather than a comprehensive culinary tour. With its high praise and awards, it remains a reliable choice for a fun and tasty day in Chicago.

Frequently Asked Questions

What is included in the tour?
The tour includes all food samples, a local expert guide, access to top attractions, and a free 2-hour bike or kayak rental (weather permitting).

How long is the tour?
The guided walk lasts about 5 hours, usually in the morning.

Where does the tour meet?
Tour check-in is at a location in downtown Chicago, with instructions to arrive 20 minutes early.

Can I do the bike or kayak rental later?
Yes, the free rental can be used within three days of booking at designated locations and times, with some restrictions.

Is the tour accessible for wheelchairs?
Yes, the tour is wheelchair accessible.

What food is included?
Expect to sample deep-dish pizza, Chicago hot dogs, Italian beef sandwiches, and brownies. The optional craft beer tasting is available for $19.99.

Can I customize the experience?
The basic package includes standard food samples and commentary. The VIP beer pairing is an add-on available upon arrival.

What should I bring?
Comfortable shoes, a camera, and a reusable water bottle are recommended.

Is gratuity included?
No, gratuity is not included and is at your discretion.

Is the tour suitable for families?
Yes, the tour’s relaxed pace and accessible routes make it appropriate for a wide range of ages and fitness levels.

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