The Bear Private Pedicab Food Tour of Chicago

If you’re looking to combine Chicago’s signature flavors, some local film lore, and a slow-paced sightseeing experience, this Private Pedicab Food Tour might just be what you need. Designed for those who want more than just a quick glance, it offers a relaxed ride through some of the city’s most charming neighborhoods with plenty of tasty treats along the way.

What we love about this tour is its casual, intimate feel — you get a guided look at Chicago’s culinary and cultural highlights while comfortably seated in a decorated six-passenger pedicab. Plus, the focus on authentic local food means you’ll be tasting some of the best Chicago has to offer, from deep-dish pizza to an iconic banana split.

One thing to consider is the duration and timing — the 2 to 3-hour window makes for a leisurely experience, but it’s still a fair amount of activity, so comfortable shoes and a love of food are recommended. This tour is ideal for food lovers, film fans, and anyone wanting a personalized Chicago adventure that blends sightseeing with delicious bites.

Key Points

• Food-focused experience with stops at renowned local eateries like Pequod’s Pizza and Margie’s Candies
• Relaxed pedicab transport providing open-air views and a fun, eco-friendly way to see the city
• Themed around Chicago and its pop culture, especially “The Bear” TV series, with iconic filming locations
• Knowledgeable guides offer insights into Chicago’s neighborhoods, landmarks, and culinary history
• Flexible schedule with options including group discounts and private transportation
• Highly rated for delicious food and engaging guides, though the tour’s length and activity level should suit those prepared for a bit of sightseeing and snacking

This private pedicab tour offers a unique way to experience Chicago—combining delicious local food, iconic city sights, and a bit of film-inspired fun. Priced at $200 per person, it’s a worthwhile expense if you value personalized attention, authentic bites, and an active but relaxed day.

Booking typically opens about 10 days in advance, making it accessible for most travelers planning a visit. With guides who are passionate and knowledgeable, you’re in good hands whether you’re a first-time visitor or revisiting the city’s beloved spots.

Your Guide to the Tour

The journey begins at Pequod’s Pizza, famous for its deep dish (more accurately, pan-style) pizza — a true Chicago classic that’s often lauded as one of the best in the city. The tour includes a personal-medium pizza, pre-ordered to avoid long waits, so you’ll get to savor a slice while comfortably seated in the pedicab. This is a fantastic way to start, as the aroma alone makes it hard to resist.

Next, the tour takes you on a leisurely ride through some of Chicago’s cutest neighborhoods, with open-air views that let you appreciate the city’s architecture and vibe. Because the pedicab is roofed but open on the sides, you’ll experience Chicago’s fresh air and city sounds while staying shaded and comfortable.

The second stop is Margie’s Candies, a Chicago staple since 1921. Here, you’ll indulge in an iconic banana split, a sweet treat that’s been delighting locals and visitors alike for over a century. The guide will explain a bit about the history of the shop and the significance of this dessert in Chicago’s culinary scene.

Crossing the Chicago River and Iconic Landmarks

From Margie’s, the pedicab will take you from the West Side across the Chicago River, offering memorable photos at LaSalle Flowers, a location that features in The Bear TV series. This part of the tour combines visual stories and the chance to snap some Instagram-worthy shots of Chicago’s skyline and river.

The open-air ride provides sweeping views of the Chicago River, with the canopy offering shade while still allowing for visceral city experiences. Expect the guides to share tidbits about Chicago’s neighborhoods, architecture, and the series’ filming locations.

The Film Connection & Optional Culinary Finish

The tour’s theme revolves around The Bear, a popular TV show set in Chicago that features several iconic landmarks. For fans, visiting La Salle Flowers and other filming sites enhances the experience, providing a behind-the-scenes perspective on the show’s Chicago backdrop.

You then have the choice to continue to Kasama, a highly-rated restaurant known for its fusion of Filipino cuisine and innovative flavors. While this stop is optional and not included in the price, it’s an excellent way to cap off your culinary adventure if you’re craving a more upscale or diverse meal.

Alternatively, the tour concludes at Mr. Beef, a legendary spot at 666 N Orleans St. Known for its authentic Italian beef sandwiches, Mr. Beef is featured prominently in The Bear and is a great spot for a hearty, satisfying meal. The guide’s insights about the significance of these locations in Chicago’s food scene make the visit all the more meaningful.

Stop 1: Pequod’s Pizza
Starting your journey with Pequod’s, you experience more than just a pizza; you taste a city’s pride. Known for its pan-style pizza, this spot’s crust, caramelized cheese edges, and hearty toppings make it a must-try. Since the pizza is pre-ordered, you won’t wait forever — a smart move that lets you start eating right away.

Stop 2: Margie’s Candies
A short ride takes you to this historic ice cream parlor. The banana split is a large, nostalgic dessert that feels like a throwback to Chicago’s old-school charm. You’ll learn about the shop’s history and the role of ice cream parlors in Chicago’s social fabric.

Stop 3: La Salle Flowers
Here, you’ll get a quick but memorable photo op of a location seen in The Bear. The guide will share some behind-the-scenes stories or film trivia, making the city’s scenery even more meaningful.

Stop 4: Kasama (Optional)
This optional stop offers a chance to indulge in creative, upscale Asian-inspired dishes. If your group feels like ending on a more refined note, Kasama provides a taste of Chicago’s culinary innovation.

Stop 5: Mr. Beef
The tour’s finale at Mr. Beef is a true Chicago experience. The Italian beef sandwich is a messy, flavorful treat, and the location’s connection to The Bear makes it especially appealing to fans. Here, you get to see the real Chicago—both its food and its streets.

The pedicab itself is part of the charm. Decorated and comfortable, it seats up to 6, but for a more relaxed experience, groups of 4-5 adults work best. It’s an eco-friendly way to cruise through neighborhoods, with guides who are both knowledgeable and enthusiastic about sharing stories, history, and culinary tips.

The food is a big highlight. Unlike typical food tours that may just offer a snack or small bites, this tour provides substantial, iconic dishes at each stop. The pizza from Pequod’s, the banana split from Margie’s, and the beef sandwich from Mr. Beef are all hearty, well-loved options that will fill you up.

The guides are often praised for their local knowledge and friendliness, adding context to each stop and making the experience more engaging. Since this is a private tour, the pace and focus can be tailored slightly to your group’s interests, which adds to the value.

The duration of 2 to 3 hours offers a good balance—enough time to enjoy the food, see some sights, and learn about Chicago without feeling rushed. The cost of $200 per person reflects the personalized nature, private transportation, and quality of food, making it a solid value for those seeking an authentic, localized experience.

This Private Pedicab Food Tour offers a rare combination of culinary delights, sightseeing, and pop culture in one relaxed package. It’s perfect for foodies, TV fans, or anyone seeking an engaging way to explore Chicago’s neighborhoods without the fatigue of traditional walking tours.

The experience’s highlight is the personalized, intimate atmosphere—you’re not just another tourist with a headset, but a guest treated to inside stories and delicious bites. The guided storytelling about Chicago’s iconic locations and The Bear filming spots enriches the experience, making it more meaningful than just a food crawl.

While the price might seem high for some, the quality of food, private setting, and expert guide make it a worthwhile investment for a memorable day in Chicago. Be prepared for a full belly by the end, and perhaps a few extra pounds if you’re not careful!

If you’re looking for a fun, tasty, and culturally immersive way to enjoy Chicago, especially if you’re a fan of its TV series, this tour is a sure bet.

Is this tour suitable for kids?
Yes, the pedicab is comfortable for children, and the stops are family-friendly, especially since it involves food and sightseeing.

How long does the tour take?
The tour lasts approximately 2 to 3 hours, depending on the group size and stops.

Do I need to book in advance?
Yes, booking about 10 days ahead is recommended, especially during peak season, to secure your preferred date.

What is included in the price?
The price covers private transportation, a pizza from Pequod’s, a banana split from Margie’s Candies, an Italian beef sandwich, and bottled water.

Can I customize the stops or itinerary?
Since it’s a private tour, you can discuss preferences with the guide, especially regarding optional stops like Kasama.

Is this tour accessible for people with service animals?
Yes, service animals are allowed on the pedicab.

What should I wear or bring?
Comfortable clothing and shoes are best, as you’ll be riding in an open-air pedicab. Bringing a hat or sunglasses for sun protection is advisable.

This tour offers a wonderful blend of Chicago’s best bites, film lore, and neighborhood charm. Perfect for those who love to eat well and soak in local culture in a relaxed, fun setting.