Exploring Chicago's Iconic Pizza Scene

Written By: Brooke Scheer

Chicago has always been close to my heart. With family roots deeply embedded in the city, I've spent countless years visiting, exploring, and falling in love with all that it has to offer. Each visit feels like a homecoming, filled with pride for a place that's intertwined with both my family's story and my personal journey. As someone who has built a career in food and hospitality, when fellow pizza lover and maker Jason Winters of Speak Cheezy presented the opportunity to join him and Steve Dolinsky, the "Pizza King" himself, on an exclusive pizza tour of Chicago, I couldn't say no. This experience was more than just a culinary adventure - it was personal. Chicago has long been hailed as a pizza lover's paradise, with styles ranging from the iconic deep dish to the crisp, cracker-thin crusts. The trip became a heartfelt dive into the soul of a city that lives and breathes pizza, and it exceeded every expectation. With Steve leading the way, Chef Jason and I had the privilege of visiting some of Chicago's most iconic pizzerias: Vito & Nick's, My Pi Pizza, Labriola, Robert's Pizza, and Pat's Pizza. Each stop had its own distinct take on pizza-making, and I left with a renewed admiration for the artistry and passion that goes into creating the perfect slice.

Vito & Nick's: A Cracker-Thin Dream

We started the day at Vito & Nick's, an iconic pizzeria and southside institution that has been slinging pizzas since 1923. Known for their thin crust, I was immediately impressed by the simplicity and boldness of their pies. Steve had us try the "Dolinsky", a tribute to Chicago's classic tavern-style pizza topped with a combination of savory sausage and tangy Italian giardiniera – a mix of pickled celery, carrots, cauliflower, and hot peppers, that adds a pop of flavor and texture to every bite. It's a pizza that speaks to the heart of Chicago's pizza tradition, offering a perfect blend of comfort and bold flavors in each slice.

Steve shared some insights into the history of this style, explaining how Chicagoans have long adored their pizzas crispy, square-cut, and cooked to perfection. The owner, Rose, was an absolute gem. Her passion for her family's business was palpable, and her pride in celebrating over 100 years of operation made the experience even more special.

My Pi Pizza: A Deep Dish Delight

Next, we headed to My Pi Pizza, an unassuming pizzeria where the deep-dish reigns supreme. As a Californian who frequents the Windy City often, I thought I knew deep dish, but this was a whole new level. My Pi's version was a revelation: a buttery, flaky crust encasing layers of Wisconsin mozzarella, chunky San Marzano tomatoes, and sausage. No need for a fork and knife here. What stood out here was the balance - the richness of the cheese, the sweetness of the sauce, and the savory sausage all worked in harmony. Unlike some heavy, overbearing deep-dish pies, My Pi's was indulgent but still left you feeling light enough to enjoy more. A definite favorite of Chef Jason's!

Labriola: My Lesson in Indulgent Pan Pizza

Labriola was next on our journey, and this spot brought something truly unique to the table. Though many Chicagoans know Labriola primarily as a bakery, they've expanded into a full dining experience with Labriola Bakery Café & Neapolitan Pizzeria. We had the pleasure of trying their pan pizza, which quickly became one of my favorites of the trip. The crust had the perfect char from the wood-fired oven, with a layer of caramelized cheese encasing it, giving the pizza a chewy texture with just the right amount of crisp. Each bite was packed with rich flavors - the tang of San Marzano sauce, the creaminess of the cheese, and the savory punch of sausage all coming together harmoniously.

This pizza was a masterclass in pan pizza - a key lesson from Dolinsky, who explained the important difference between deep dish and pan pizza. While deep dish has a significantly deeper, bowl-like crust with tall sides, pan pizza has a more evenly thick crust throughout, often with a slightly crispier exterior. Labriola's pan pizza beautifully showcased this distinction, offering an unforgettable experience that stood apart from traditional deep-dish pies.

Robert's Pizza: Where Gourmet Meets Comfort

Robert's Pizza has become a must-visit destination for gourmet pizza lovers in Chicago, and after our stop there, it's easy to understand why. Their pizza comes with a special twist - Robert's uses a sourdough starter for their dough, much like our beloved recipe at Speak Cheezy. This gives the crust an extra layer of depth and flavor that sets it apart. We had the pleasure of trying the fennel pizza, topped with braised fennel, fennel fronds, fennel salami, fennel pollen, fresh mozzarella, and a drizzle of sweet honey. It was a beautifully balanced and elegant pie, bursting with flavors that complemented each other perfectly. With the serene backdrop of the patio seating along the river, Robert's Pizza felt both gourmet and approachable. It's no wonder they've earned a place at #50 on the list of the Top 100 Pizzerias in the World - an achievement that truly speaks to their quality.

Pat's Pizza: A Taste of Tradition

Our final stop was Pat's Pizza, another cherished family-owned Chicago institution known for its classic thin-crust pies. The pizza here was a true homage to tradition - no frills, just pure, unadulterated pizza. We tried the "Dolinsky" once again to compare the distinct difference in thin-crust styles between the south and north sides of Chicago. The crust was perfectly crispy, the cheese melted to perfection, and the toppings were fresh and simple, just as they should be. It was the kind of pizza you could enjoy for hours, sitting with friends and savoring slice after slice. Steve emphasized that this kind of pizza embodies the true spirit of Chicago—a city that deeply loves its pizza but doesn't need to overcomplicate it to make it exceptional.

The Takeaway

As our tour came to an end, I found myself not only in a blissful food coma but truly enlightened about Chicago's rich pizza culture. Chicago's pizza scene is much like its people - diverse, bold, and full of heart. From the cracker-thin slices at Vito & Nick's to the indulgent deep dish at My Pi Pizza and the gourmet creativity at Robert's, each stop offered a unique and delicious experience. Steve Dolinsky's extensive knowledge of the city's pizza culture made the journey even more special. He didn't just introduce us to the pizzas; he shared the stories behind them, which made each bite all the more meaningful.

If you ever find yourself in Chicago, I can't recommend taking a pizza tour enough. Pizza City USA offers both bus and walking tours featuring the city's most iconic pizzerias. It's more than just a culinary adventure - it's a journey into the heart of a city that takes its pizza seriously. Whether you're a fan of the classic thin crust or crave a deep dish stuffed with all the fixings, Chicago has you covered. And trust me, you'll leave with a newfound appreciation for every style of pizza, and perhaps even a craving for just one more slice.