It sounds like a contradiction, but plenty of New Yorkers catch themselves searching for the best deep dish pizza in Chicago after one great trip to the Midwest — and then remember they live 700 miles from the Loop. Here is the local secret: New York already bakes thick, pan-born pizza that answers the same craving, and arguably beats it on texture. Sicilian squares and grandma slices deliver the crisp, almost fried bottom, the assertive sauce, and the knife-and-fork heft that deep dish devotees miss, without an airport in between. This guide works like a decision tree: figure out what you are really craving, then follow the branch to the right counter.
Standing in a slice shop wondering if you picked the right one? Text Karpo in iMessage and it will match your craving to the nearest square, tell you how the line is running, and coach your order before you reach the register.
Know your square before you choose
A quick taxonomy, because the terms get blurred. Deep dish is a tall-walled pie with cheese buried under a lake of sauce, baked in a round pan and eaten with cutlery. A Sicilian square is its New York cousin: a thick, airy, focaccia-like sheet-pan dough with a caramelized underside. A grandma slice is the sleeper hit — thinner and denser than a Sicilian, stretched into an olive-oiled pan the way Italian grandmothers made it at home, usually with garlicky crushed-tomato sauce striped over the cheese. If the best deep dish pizza in Chicago is about depth, New York squares are about ratio: crust, crisp, sauce, and chew in balance.
Now the routing. Want the closest spiritual match to deep dish, with history attached? Head to L&B Spumoni Gardens. Need pepperoni above all? Prince Street Pizza. Chasing whatever critics currently call the world's best? Mama's Too. Prefer something lighter and more modern? Fini Pizza. Each branch below tells you where, when, and what to order.
If you want old-school heft: L&B Spumoni Gardens
The Bensonhurst institution at 2725 86th Street has been feeding Brooklyn since 1939, and its Sicilian square is the borough's closest answer to deep dish gravity. The construction is famously upside-down: mozzarella goes on the dough first, sauce is ladled over the top, and a dusting of pecorino finishes it, so the cheese fuses into the crumb while the sauce stays bright. Skip the sit-down dining room and order at the dedicated walk-up pizza window outside — a separate window handles the spumoni, the tri-color frozen dessert you should absolutely get afterward. The shaded picnic tables fill with multigenerational families on weekends. Doors are open daily from 11 in the morning until 11:30 at night, so a late-evening square under the umbrellas is a legitimate plan.
If pepperoni is the point: Prince Street Pizza
The Nolita shoebox at 27 Prince Street built its reputation on one item: the Spicy Spring, a Sicilian square layered with spicy Fra Diavolo sauce, fresh mozzarella, pecorino, and thick-cut pepperoni that curls into crisp little cups holding pools of chili-tinted oil. The line is a fact of life here, but it has two weak points — the shop opens at 10 in the morning, and the first hour is the calmest the sidewalk ever gets. Better yet, since April 2026 there has been a second New York location at 271 Smith Street in Carroll Gardens, serving the same squares until midnight most nights — 3 in the morning on Fridays and Saturdays — with a fraction of the Nolita wait. If your visiting friend insists Chicago pepperoni is superior, this is the slice you hand them before continuing the argument.
If you follow the critics: Mama's Too
In February 2026, Time Out ranked the slice at Mama's Too, 2750 Broadway on the Upper West Side, the single best pizza in the world — not in New York, in the world. What earned it is engineering: the pepperoni square arrives with a frico crust, the ring of browned, lacy cheese where the dough meets the hot pan, and a crumb that stays custardy inside. Regulars branch out to the Angry Nonna, which piles hot soppressata over aged mozzarella and finishes with Calabrian chili oil and hot honey. Hours run noon to 11 nightly, and the counter moves faster than the hype suggests — a weekday mid-afternoon visit often clears in twenty minutes, while peak lunch and dinner stretch much longer. A West Village sibling now spares downtowners the trip uptown.
If you want it lighter: Fini Pizza
Grandma style is the branch for people who love the idea of a square but not the density, and Fini Pizza at 305 Bedford Avenue in Williamsburg makes the case elegantly. The shop comes from Sean Feeney, the restaurateur behind the pasta destinations Lilia and Misi, who applied fine-dining sourcing to a neighborhood slice counter. The grandma here is thinner than a Sicilian, olive-oil crisp at the bottom, with a balanced sweet-savory sauce that does not bury the crust. It keeps honest neighborhood hours, noon to 10 every day, and there is an outpost inside Barclays Center if you are catching a game. This is the square to eat while walking Bedford Avenue rather than the one that ends your afternoon.
Route it like a local
Putting the tree together: hosting a deep-dish loyalist for a weekend, start them at L&B and let the upside-down square do the talking. Downtown with one free hour, hit Prince Street at the 10 a.m. open, then walk Nolita while everyone else stands in line. Museum day uptown, fold Mama's Too into the afternoon between stops. Date night in Brooklyn, make Fini the walking snack before dinner. Whichever branch you take, you will stop searching for the best deep dish pizza in Chicago from a city that solved the thick-crust question its own way.
Practical notes
Transit is straightforward for all four: L&B sits a short walk from the 25th Avenue and Bay Parkway stations on the D line in Bensonhurst, Prince Street Pizza is minutes from the Prince Street R W station, Mama's Too is beside the 103rd Street 1 train, and Fini is a five-minute walk from the Bedford Avenue L stop. All four are counter-service shops that take cards, and none takes reservations for slices — if you want a whole pie or a half-tray from L&B, call ahead, especially on weekends. Lines peak at lunch, weekend afternoons, and the hour after sunset; late morning and mid-afternoon on weekdays are the calm windows. L&B's seating is outdoors at picnic tables, so check the weather, and note the Carroll Gardens Prince Street location runs until midnight on weeknights while Nolita goes later still.
Tags: #nycpizza #grandmaslice #sicilianpizza #brooklynfood #bensonhurst #nolita #upperwestside #williamsburg #nycfoodie #squareslice #pizzalovers #nyceats #neighborhoodguide
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Ask Karpo first
Want to know which window to order from, when the picnic tables clear out, or whether the Smith Street line is shorter than Nolita's right now? Ask Karpo for the latest square-slice updates, a craving-matched shortlist, and a live route from Bensonhurst to Williamsburg before you head out.
