Every Chicago transplant in New York hits the same wall around week three: the craving. Not for skyline views or Lake Michigan, but for a knife-and-fork pie with a buttery crust and a molten interior that takes half an hour to bake. The bad news first — nothing here will perfectly clone the best deep dish pizza in Chicago, and the sooner you stop demanding it, the happier you'll eat. The good news: New York's pizza bench is deep enough that homesick Chicagoans tend to follow a predictable arc, from hunting replicas to going fully native. This guide maps that arc — what visitors and brand-new arrivals do, what settled transplants actually do, and where the two camps finally agree.
Homesick and hungry is no way to plan dinner — ask Karpo which of these pizzerias is closest to you right now, whether the wait is worth it tonight, and what a first-timer should order.
What visitors do: hunt for a deep dish clone
The first stop on every homesick itinerary is Emmett Burke's little Chicago empire. Emmett's on MacDougal Street in SoHo has been baking genuine deep dish since 2013, and for a visitor with one night in town, it is the closest thing to a direct flight home. But the move insiders know is his second act: Emmett's on Grove, at 39 Grove Street in the West Village, which skips deep dish entirely in favor of Chicago's true hometown order — tavern-style thin crust, rolled cracker-thin, baked extra crispy, and party-cut into shareable squares. Chicagoans know the secret that the best deep dish pizza in Chicago is mostly for special occasions and out-of-towners; the tavern cut is what locals there actually eat on a Tuesday. Order the Hot Poppy, book ahead, and note the supper-club room only gets going from late afternoon onward.
What transplants actually do: defect to the square
Give it a few months and something shifts. The transplant stops chasing depth and discovers that New York has its own pan-pizza religion, older than most of Chicago's famous rooms. L&B Spumoni Gardens has been serving Sicilian squares in Gravesend since 1939, and the build is the revelation: the mozzarella goes down first, directly on the dough, with the tomato sauce ladled over the top so the cheese fuses into the crust and the sauce stays bright. It is the same upside-down logic that makes deep dish work, compressed into a two-inch square you can eat standing at a picnic table with a cup of spumoni waiting. The 86th Street original runs long hours daily, and there is now a Dumbo outpost by the Brooklyn Bridge for anyone who can't face the trek.
The natural second stop is Emmy Squared at 83 First Avenue in the East Village, the room that taught downtown Manhattan to argue about Detroit-style pizza. Its squares rise fluffy in the middle, crisp underneath, and carry a caramelized frico halo from cheese baked directly against the pan walls, with the sauce striped on after the bake rather than buried below. For a Chicagoan raised on sauce-on-top construction, it reads as instantly familiar and completely different at once — proof that the upside-down build is a shared dialect between the Midwest and New York, not a monopoly held by the best deep dish pizza in Chicago. Come at lunch on a weekday and the corner pieces, the ones with two caramelized edges, are still on the board.
Where both camps agree: the fold
Full conversion arrives the night you fold a slice without thinking about it. Joe's Pizza on Carmine Street has been the city's reference slice since 1975, when Joe Pozzuoli of Naples opened the standing-room counter that still refuses to modernize; it stays open until 3 a.m. most nights and 4 a.m. on Friday and Saturday, which is precisely when a transplant's loyalty finally flips. For the sit-down version of the argument, Rubirosa in Nolita bakes an ultra-thin Staten Island-style crust that makes even tavern cut feel thick, crowned by the Tie-Dye pie — vodka sauce, tomato, and pesto swirled over fresh mozzarella. Walk-ins routinely face two-to-three-hour waits, so grab a Resy or put your name in and wander Mulberry Street. Neither room will remind you of the best deep dish pizza in Chicago, and that is exactly the point: this is the stuff you'll miss when you eventually leave New York.
The transplant's cheat sheet
Week one, homesick: Emmett's on MacDougal for actual deep dish. Month one, curious: Emmett's on Grove for the tavern cut Chicagoans quietly prefer. Month three, converting: L&B's upside-down Sicilian square and Emmy Squared's frico-edged Detroit pan. Month six, native: a folded Joe's slice at 2 a.m. or a Tie-Dye at Rubirosa, defending New York pizza to your visiting parents. The craving never fully dies — it just gets outvoted, one square at a time. Keep the phases in order: skipping straight to the slice era means missing the squares entirely, and the squares are where a Chicago palate and a New York pantry actually make peace.
Practical notes
Everything here is subway-friendly. Emmett's on Grove sits two blocks from the Christopher Street 1 train, and Joe's on Carmine is a short walk from the West Fourth Street hub; Rubirosa is closest to Spring Street on the 6, and reservations there go fast on Resy, so book ahead or expect a multi-hour walk-in wait at dinner. Emmy Squared is near the First Avenue L and takes reservations. L&B Spumoni Gardens is the one real journey — deep in Gravesend on 86th Street, open late morning to late night daily — though the Dumbo location near the Brooklyn Bridge shortens the trip. Cards are fine in every dining room, but carry some cash for L&B's walk-up window just in case. Squares there move fastest from that window; order spumoni before you think you want it.
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Ask Karpo first
Wondering whether the Rubirosa wait has cleared, when L&B's takeout window is calmest, or how to string three of these pizzerias into one afternoon? Ask Karpo for the latest NYC pizza intel, a homesickness-proof dinner plan, and a live route from the West Village to Gravesend before you head out.
