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This feature is not meant to settle arguments about which style is best—as if we could—but rather to celebrate the blessed landscape. So I, a man with a huge pizza passion and no deep-seated regional biases, spent months in search of pies that were particularly fresh, balanced, and distinctive. This being Chicago, I found them in every corner of the city and suburbs. Here, the 25 tastiest pizzas in town and where to get them. (Launch the gallery.) Plus, “64 Lines About 32 Pizzas,” my song and video tribute to the world of Chicago pizzerias.
Cremini mushrooms, Dante cheese
Thin: Nick Lessins, the chef/owner of Great Lake, is not just in a league of his own; he’s the only one playing his particular sport. You may have heard him called a genius, a god, or a grump, depending on whom you ask and how long they waited for their pizza, but I’ve spent enough time in his tiny Andersonville storefront to conclude that he is none of the above. Lessins—a man with two college degrees and no car—is simply more dedicated and consistent than the competition. Whether the line is out the door or he’s stone alone, the Detroit native focuses on his craft rather than his customers, a fact that a percentage of the public will never understand, much less accept. But he’s exactly the same as he was before GQ, Food & Wine, The New York Times, and everyone else began telling him how great he was. Maybe better.
The creations he shapes so meticulously at his 12-seat BYO are launching pads to remarkable galaxies of flavor that no other Chicago pizzamaker comes close to matching. In his inspired combinations (only three options a night, depending on how Lessins feels and what he finds at the market), smoked bacon may dance with viscous crème fraîche and chives; roasted sunchokes might whisper sweet nothings to sheep’s milk cheese. His latest beauty has a legion of thin, black-peppery cremini mushrooms sinking into decadent aged Dante cheese on a dynamic, bulbous crust. The bread’s collar emphasizes a minuscule crispy exterior embedded with sea salt; its interior is impossibly airy. How Lessins coaxes such miracles from his tiny Montague HearthBake gas oven is one of Chicago’s great mysteries and treasures. 1477 W. BALMORAL AVE.; 773-334-9270
Plain with artichoke hearts
New Haven: When Billy Jacobs opened Piece in 2001, he was told New Haven– style pizza would go over like a lead pepperoni in Deep-Dish Land. Wrong. Piece’s astonishing plain pie (sauce, garlic, Parmesan, and oil on a chewy-crisp, hand-formed crust) replicates New Haven’s legendary Sally’s Apizza without the coal oven (Piece uses a Middleby gas oven). For Jacobs, a Connecticut native whose great-uncle’s produce market was intertwined with Sally’s in the 1940s, the sun still rises and sets in New Haven. “I can confidently say that the third-, fourth-, or even fifth-best pie in New Haven would be the best pie almost anywhere else,” he boasts. And you thought New Yorkers were pizza snobs. 1927 W. NORTH AVE.; 773-772-4422
Neapolitan: At some point, we’ve all done “pizza math,” wherein you silently tally the number of slices everyone has eaten before deciding whether you’re allowed to grab another one. At Castel Gandolfo, a criminally underappreciated place with a coal-fired oven, I avoid this dilemma by going alone. I order the tremendous 14-inch Margherita takeout and marvel at it for a moment: concentric circles of oregano-sparked sauce, melted bufala mozzarella, big basil leaves, and a sooty crust besieged with majestic bubbles. Then I eat the whole damn thing on the steps of a brownstone around the corner. The math is easier that way. 800 N. DEARBORN ST.; 312-787-2211
Thin: A traditional German Flammkuchen (“flame cake”) is basically a thin pizza with crème fraîche instead of tomato sauce, similar to the tarte flambée that the Alsatians claim just over the border in France. In Wicker Park, Crust replaces crème fraîche with caraway-seasoned béchamel, reinforcing it with crisp bacon chunks and flawlessly caramelized purple onions. The béchamel basically serves as the sauce and the cheese, allowing the char-marked crust some room to breathe. The effect is so creamy and clean you can’t help but turn up your nose at the greasy muddle that passes for most American pizza. 2056 W. DIVISION ST.; 773-235-5511
Neapolitan: After softball games at Union Park, which my team almost always loses, we often go to Coalfire. No matter how much we order, it’s never enough. Last time, we polished off eight pies (which may have been linked to the losing). The issue, if you can call it that, is how easy Coalfire’s East Coast–style pizzas are to eat: After two minutes in the oven, they come out so deliciously smoky, pliable, and light that each slice takes about 45 seconds to polish off. You just sort of keep going, and next thing you know, the team’s in last place. 1321 W. GRAND AVE.; 312-226-2625