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Chicago pizza without a doubt. The deep dish is OK when you're in the mood, but Chicago medium crust from the right place kills NYC's greasy thin pizza.
I don't have enough experience with New York pizza to have an informed opinion. I've only had a couple of New York pizzas and enjoyed them. I've also enjoyed many hundreds of Chicago pizzas, both "old neighborhood" thin crust and deep dish.
To tell the truth though a pizza has to be really bad that I don't enjoy it. Like Giordano's and Geno's East in Chicago, I'd rather have a frozen Red Baron than those.
New York for pizza. Not only do I love thin crust foldable pizza, but we also have Totonno's in Coney Island and Patsy Grimaldi's in DUMBO--two very different but both incredible pies. Also, New York is close to New Haven, with its own utterly delectable style of pizza (like at Frank Pepe's.)
Chicago, however, takes it for hot dogs, because the dogs are just as good and you can get so many awesome toppings. ALSO, Chicago Italian beef sandwiches slide in just on top of Philly cheesesteaks and hoagies as the BEST CITY-SPECIFIC FOOD IN AMERICA. Those sandwiches are heaven, especially if you get them as a combo with a sausage in it too.
Not all NYC pizza is saggy and greasy like that nasty Dominos Brooklyn style pizza
Infamous has brought up a good point, although hopefully when someone says the words "New York" and "pizza" in the same sentence, they're not referring to that nasty franchise stuff. If there was justice in the world, franchise pizzerias would be banned from New York. And Chicago, for that matter. If you live in either city and go to Domino's (or Papa John's, or any such place) for your pizza, then you get what you deserve.
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