Chicago Pizza Tour

Experience the Flavor of Chicago’s Pizza Scene on a Guided Tour
Imagine exploring Chicago through its most beloved food—pizza. For just $89 a person, this Chicago Pizza Tour offers a 3.5-hour journey into the city’s iconic neighborhoods, with stops at four different pizzerias. Led by knowledgeable local guides—often full of humor and fascinating stories—you’ll get to taste a variety of pizza styles, from classic deep dish to thin tavern crust and coal-fired pies. Transportation is included, making it easy to hop from one neighborhood to the next without the hassle of parking or public transit delays.

What we really appreciate about this tour is how it combines delicious food with local history. The guides are praised for their warmth and expertise, making the experience both fun and educational. Plus, the small group size means there’s plenty of opportunity to ask questions and share opinions—no giant bus crowd here.

A possible consideration is the pace—if you’re not used to walking or standing for extended periods, keep that in mind. Also, since it’s a food-focused tour, skipping breakfast beforehand is wise to genuinely enjoy each slice. This tour is best suited for food lovers, history buffs, and anyone interested in seeing different parts of Chicago beyond the usual tourist spots.

Key Points

• Diverse pizza styles: From deep dish to thin crust, coal-fired, and New Haven style.
• Neighborhood exploration: Four different areas showcase Chicago’s vibrant food culture.
• Expert guides: Knowledgeable, funny, and passionate about pizza and Chicago history.
• Inclusive experience: All stops include a slice of pizza; great for shared dining and conversation.
• Transport included: Mini-coach ensures smooth travel between neighborhoods.
• Small groups: With a maximum of 20 travelers, it’s intimate and engaging.

Exploring Chicago Through Its Pizza Scene

Chicago’s pizza scene is legendary—an edible blueprint of the city’s immigrant roots, innovative spirit, and local pride. This guided tour offers a fantastic way to sample that history without the hassle of choosing restaurants or navigating unfamiliar neighborhoods.

The tour begins at a well-known pizzeria, Pizano’s, located near the bustling Magnificent Mile. Here, you’ll get a quick lesson on Chicago’s iconic deep dish pizza, often seen as the city’s signature dish. The slice is as hearty as you’d expect, with a buttery crust, gooey cheese, and rich tomato sauce. As one reviewer put it, “The guide was hilarious and extremely knowledgeable about the history of deep dish pizza and the city as a whole.” This initial stop sets the tone—delicious, authentic, and packed with stories.

After the first taste, your guide — possibly James, if reviews are any indication — will lead you to a mini-coach for the next neighborhood. The journey itself is part of the fun, as you drive through vibrant districts, getting a glimpse of Chicago’s diverse architectural styles and local vibe.

In-Depth Look at Stops and What Makes Them Special

Stop 1: Pizano’s Pizza (Magnificent Mile)
Located in a central and historic part of town, Pizano’s has roots dating back to 1943. It’s closely tied to the creation of Chicago’s famous deep dish, making it a must-visit for pizza aficionados. Expect a slice from a restaurant that’s practically part of the city’s culinary fabric. One reviewer mentioned, “The guide shared the history of Chicago deep dish while we enjoyed a slice from one of the best purveyors.”

Stop 2: Flo & Santo’s in Grant Park
Just steps from Grant Park, this spot offers Chicago’s thin crust tavern-style pizza, a lighter, crisper alternative to deep dish. The owners are a Polish grandma and an Italian grandpa, blending flavors from their backgrounds. This fusion is a delightful twist, with an emphasis on the social, casual tavern experience. “Flo was the Polish grandma and Santo was the Italian grandpa, so this menu is a fusion of both flavors,” notes a reviewer.

Stop 3: Pequod’s (Lincoln Park)
A true local legend since 1971, Pequod’s is famous for its caramelized crust, achieved by a special burnt cheese method that creates a crispy, flavorful edge. Reviewers rave about their “burnt cheese caramelized crust with the sweet sauce,” making it a memorable stop for serious pizza fans. It’s a bit off the typical tourist trail, which adds to its charm.

Stop 4: Coalfire (United Center area)
In the West Town neighborhood, Coalfire offers coal-fired pies, baked at temperatures exceeding 1000 degrees. The result? Pizzas with a distinctive, smoky flavor and a perfectly crisp crust. It’s a different take on pizza that has gained local and national acclaim. “Getting pizza in West Town can only mean one thing, Coalfire,” says one guide, highlighting its reputation.

Stop 5: Coalfire Southport (Wrigleyville)
Up north, near Wrigley Field, this second Coalfire location continues the coal-fired tradition. This neighborhood is lively and sports-oriented, perfect for grabbing a slice before or after a Cubs game. “Enjoy some of the best pizza in Chicago in one of the best neighborhoods the city has to offer,” a review notes.

Stop 6: Piece Pizza in Wicker Park
Rounding out the tour is Piece Pizza, known for New Haven-style pies. It’s a contemporary flavor, offering a break from the more traditional styles, and remains a favorite among tour regulars. “Their New Haven style pies have been enjoyed on the tour ever since we opened,” notes a reviewer, emphasizing how this stop consistently delights.

What to Expect During the Tour

You begin with a downtown meeting point, where your tour guide greets you and quickly shares the history of Chicago pizza. From there, it’s a mix of walking, riding, and eating, with stops lasting about 30-45 minutes each. The transportation by mini-coach is comfortable and air-conditioned, vital given Chicago’s unpredictable weather.

Each stop includes a slice of pizza, with options to purchase extra drinks—an added bonus for pacing yourself or enhancing the experience. The tours draw a vibrant, diverse crowd—local residents, travelers, and repeat visitors, all here to enjoy Chicago’s pizza heritage.

The pacing is generally well-balanced, allowing time to savor each slice and soak up local stories. Guides are praised for their humor and wealth of knowledge, making the experience both educational and entertaining. “James was an amazing guide,” one review states, “full of knowledge about the city and pizza.”

Food and Sightseeing Combined

While the tour’s main focus is pizza, the neighborhoods themselves offer a glimpse into Chicago’s varied character. From the bustling Magnificent Mile to the laid-back vibe of Wicker Park, you’ll see a slice of local life. The drive through neighborhoods allows for a relaxed overview, especially if you’re new to the city.

The pizza itself is the star—each place serving a signature style that highlights Chicago’s culinary diversity. You’ll learn about the ingredients, baking techniques, and cultural influences that make Chicago pizza unique. For example, Pequod’s’s caramelized crust is a definite highlight, as is the smoky flavor of Coalfire’s coal-fired pies.

Authentic Experiences and Honest Opinions

Reviewers consistently note the tour’s authenticity and fun atmosphere. Many have done the tour multiple times, appreciating how each visit brings new insights or different restaurants. “This is my third time doing this tour,” a reviewer shares, “and each one is different with new restaurants.”

The guides’ storytelling and humor add to the experience, making each stop more than just a taste test. They share local lore, pizza trivia, and personal anecdotes, making the history feel alive.

Some minor drawbacks mentioned include the possibility of the pizzas not being “super wowed” at every stop, but most agree the overall experience is well worth it. The tour is designed for those who are genuinely hungry and ready to eat, so a light breakfast is recommended.

The Sum Up: Who Should Consider This Tour?

If you’re a pizza enthusiast eager to taste multiple styles and learn their origins, this tour is a treasure. It’s perfect for food lovers who want a relaxed, informative day exploring Chicago’s neighborhoods and culinary traditions. The small-group setting ensures a personal, engaging experience—ideal for travelers, locals, or anyone with a curiosity for Chicago’s food culture.

For those who enjoy stories behind the food, this tour offers a lively mix of history, humor, and deliciousness. It’s also a great choice for families with older children who can appreciate the variety of flavors and the city’s stories.

While not a casual, quick snack, it offers genuine value—sampling some of the city’s best pizzerias in one afternoon, with expert guidance and a friendly vibe. For anyone wanting to see Chicago through its most iconic dish, this tour will leave you full of food, stories, and a newfound appreciation for the city’s pizza mastery.

FAQ

How long is the tour?
It lasts approximately 3 hours and 30 minutes, including travel and tasting stops.

What does the tour include?
You get four slices of pizza at different pizzerias, transportation by an air-conditioned mini-coach, and a knowledgeable local guide.

Are drinks included?
No, drinks are not included, but there is an opportunity to purchase additional beverages at each stop.

Is this tour suitable for children?
Children under 6 are free but should be notified to reserve a seat. Most travelers with older kids find it enjoyable, especially if they love pizza.

Are there any dietary considerations?
The tour is focused on pizza, so if you have allergies or specific preferences, it’s best to check with the operator beforehand.

What neighborhoods are visited?
Stops are made in the Magnificent Mile, Grant Park, Lincoln Park, West Town (near United Center), Wrigleyville, and Wicker Park.

Is transportation included?
Yes, the tour offers transport by mini-coach between stops for comfort and convenience.

Do I need to book in advance?
Yes, most people book about 38 days ahead, but last-minute availability can be checked.

What is the maximum group size?
The tour is capped at 20 travelers, ensuring an intimate experience.

Can I cancel if my plans change?
Yes, you can cancel for free up to 24 hours before the tour, getting a full refund.

This guided pizza tour in Chicago offers more than just a meal—it’s a culinary adventure through the city’s neighborhoods, culture, and history. Perfect for those with a hearty appetite and a love for authentic, memorable food experiences.