We Went to Chicago to Find the Best Pizza—Here’s What We Found

Some trips are booked for business. Some are booked for fun. And then there’s the rare trip that manages to be both—like our recent pizza pilgrimage to Chicago.

The plan was simple: try a ton of pizza, review it, and find out what makes Chicago slices stand apart. What happened was something better—we got a great meal in just about every zip code, and something about walking city blocks with a greasy slice in hand gave our team a new kind of energy. The day was pure delight as we hung out, stepped aside from the business as usual, hared stories over crust and sauce, and got out our score cards to be the judges of the best Pizza in the city.

First Impressions (and First Slices)

Landing in Chicago, the air had that chill that keeps your hoodie up and your senses sharp. We made our way to D’Amato’s Bakery, where the smell of warm bread hit like a welcome sign. A cozy, no-frills spot with character on the walls and history in every bite, it set the tone for what would become a deeply satisfying tour of flavor and texture across the city.

From there, we ventured into the Harry Potter Experience, an unexpected detour that turned out to be a full-on wand-waving adventure. Between robes, replica wands, and a sidewalk stag that looked like it stepped out of a movie set, the whole visit added a little magic to the day.

Later, we closed the day with one of the most iconic Chicago experiences—The Ledge at Willis Tower. Suspended 1,353 feet above the city in a glass box, you get a perspective you can’t unsee. It was breathtaking, surreal, and maybe a little nerve-racking, but everyone took that step—together, the group photo says it all.

The Pizza Mission

Of course, the reason we came here was for pizza—and Chicago did not disappoint. As part of our official Pizza Crawl Review, we covered a range of styles and neighborhoods, tasting everything from buttery tavern-style to crisp thin crust, each slice telling a different story.

You can read all the official reviews here, but let’s just say: the debate over best slice got louder with each stop. There were surprises. There were favorites. There were opinions—and then more pizza.

A Team That Eats Together

The rare chance to gather, outside the back-and-forth of daily emails and project deadlines, and see each other in a new light. This was the first time our team—Kurt, Dylan, Michael, Andrew, Sherry, Peter, Tom, and our newest addition Leo—were all together in one place, outside of work. And something clicked. Conversations that usually happen in inboxes turned into real moments between bites. Energy shifted. Trust grew. Everyone brought their A-game… and their appetite.

There was an exciting momentum to the day as the pizza opinions compounded as we indulged in Pizza Pie after Pizza Pie.

Why Chicago?

It’s a city that knows how to mix grit with beauty, attitude with generosity, where Skyscrapers meet mom-and-pop bakeries, and where you can go from architectural awe to butter crust within a few blocks.

If you’ve never been, go. If you’ve already gone, go again—with people you enjoy. Because Chicago has this way of pulling you into its rhythm, one slice, one view, one laugh at a time.