When Kathryn Robin and Mark de Roo read our November 2023 rankings of our 25 favorite pizza joints, they took it, in their words, as “a citywide invitation.” 

“Pan, deep dish, tavern cut, Sicilian, Neapolitan. Old guard and new blood. Neighborhood institutions and ambitious newcomers. It mapped Chicago through dough, sauce, and time,” they wrote in a recent e-mail to us. “We looked at each other and said, should we try them all?” 

And that they did. All 25. Equipped with the list of restaurants and an elaborate spreadsheet — their own assessments factored in crust, sauce, cheese, toppings, and overall taste — the two began at Sfera Sicilian Street Food on November 5, 2023. Two years later, on December 26, 2025, they crossed the finish line at George’s Deep Dish.

“Growing up and being here my whole life, I didn’t know a lot of these places,” Robin says. “They felt fresh and new, not like the usuals. That’s what I love about Chicago. We’re all in this city together, learning and exploring.” 

The pair used the pursuit not just as an opportunity to explore unfamiliar pizza joints and neighborhoods but as a way to spend time together in a long(ish)-distance relationship: Robin, who works for a mortgage company, lives in Wheaton (she grew up in the Chicago suburbs and lived in Lincoln Park after college), and de Roo, a leadership coach, lives in Holland, Michigan. 

The pizza they would try on any given day largely depended on their schedules, which added an air of spontaneity to the exercise. When de Roo was coming back from visiting his kids on the East Coast for Thanksgiving, his flight got diverted and he had to take a bus from Cleveland to Chicago for the last leg. “Getting in at 10 o’clock in the morning, Kathryn nicely picked me up — and maybe not even a mile from the bus station was one of our pizza joints,” he says.

The couple estimates they traveled some 2,500 miles across the Chicago area in pursuit of pizza — but they consider that a worthy tradeoff for the good bites and the folks they met along the way. “What struck us was how much all of these business owners just love what they do,” Robin says. “They really take pride in it. The last restaurant we were at, George’s, his mom was there working. We were just chatting up a storm, hearing their struggles of how hard it is to open a restaurant and keep it sustained. You don’t realize that when you just walk in, get pizza, and go home.” 

Now, after their two-year odyssey, Robin and de Roo have crafted their own rankings — “not as a challenge to the original list,” they wrote in their e-mail, “but as a reflection of what stayed with us long after the plates were cleared.”

Their top five:

1. Villa Nova
2. George’s Deep Dish
3. Sfera Sicilian Street Food
4. Robert’s Pizza and Dough Company
5. Bungalow by Middle Brow

“We expected great food,” the couple added in their email. “We didn’t expect how meaningful the journey would become. Chicago pizza isn’t a single thing — it’s a conversation. We wanted to share this story because your list didn’t just spark debate—it sparked movement. It encouraged us to wander, to stay longer, to talk to strangers, and to experience the city slice by slice.”