Chicago Style Pizza

The Stuffed Pizza at Chicago Style Pizza is a pie built inside another pie — dough pressed up the sides, then sauce, toppings, and a cheese blend, sealed under a second layer of dough and finished with more sauce across the top. The menu asks for thirty minutes, and that number sets the tempo for the whole table. This is deep dish treated as an occasion rather than a quick slice: the order a group on Hamilton Mountain settles in around, served from a long-standing Italian kitchen on Upper Sherman Avenue, just off Concession Street.

The named pies carry their own character. The Chicago Special arrives under Italian sausage, green pepper, and mushroom; the Shack Special comes fully dressed in pepperoni, green pepper, mushroom, onion, and green olive; the Cosmopolitan, the vegetarian option, layers tomato, black olive, onion, fresh garlic, and hot pepper. They come in two formats — a six-slice ten-inch and a ten-slice fourteen-inch — both generous enough that sharing is the assumption rather than the exception. The menu's true oddity is the Pizza Sub, an open-face submarine under garlic butter, pizza sauce, and mozzarella that the kitchen calls its own invention, carried north from Chicago.

Past the pizza, the cooking leans hard into Italian-American comfort. Baked rigatoni comes in a mushroom-meat sauce with meatballs and melted mozzarella; lasagna and cannelloni stuffed with seasoned beef and pork hold the heavier end; eggplant parmigiana and the Match Made in Heaven plate — a meat cannelloni set beside a spinach manicotti — cover the in-between. The Vitello and Pollo section adds chicken parmigiana and a chicken red and white, and gnocchi rounds out a pasta list that runs well past the pies. Portions skew large across the board, the kind that send a table home with a second meal.

That thirty-minute bake is the thing to plan around, and the menu is quietly arranged to make the wait pay off. The move is to open with the appetizer list — fried ravioli in tomato or picante sauce, battered mushrooms, or the Appy Platter that puts both on one plate — so there is something crisp to share while the oven does its work. A diner who would rather skip deep dish has the whole pasta side to fall back on, which is what makes it forgiving for a mixed group: one person waits on the Stuffed Pizza, another orders baked rigatoni, and the table never has to agree. When the evening stretches, the tiramisu — mascarpone, espresso, and a little rum over an Oreo-crumb base — is the unhurried finish.

The Chicago in the name is not borrowed branding. The family behind the restaurant traces its cooking to Triggiano, in the Puglia region of southern Italy, then to a Chicago chapter that began in 1946, before those recipes followed the family to Hamilton in the 1970s. The Upper Sherman kitchen opened in 1979 and has stayed in family hands since, which is why the menu reads less like a concept than an inheritance — the deep-dish format, the house sauces, and that transplanted Pizza Sub all handed from one kitchen to the next.

For regulars, the calendar matters as much as the menu. Tuesday brings a deal on a large pizza with three toppings, Wednesday turns on baked rigatoni, and Thursday is the night a small Stuffed Pizza comes with toppings built in — a standing weekly rhythm that rewards the diners who plan around it. The deals are narrow on purpose — three nights, three dishes — and that restraint is part of why they stick. It accounts for the name the restaurant answers to online, the Shack, and for the way the Mountain talks about the place: not somewhere you try once, but the deep-dish answer the neighbourhood keeps circling back to, thirty-minute wait and all.