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.
Menu Tags
What to order
Tiers reflect how diners actually talk about each dish — Diamond is the rarest. Tap a dish to cast your vote.
Stuffed Pizza is a true planning dish, not a generic pizza order: layered dough, sauce, toppings, cheese, another dough layer, and a 30-minute bake.
02
Comfort Beyond Pizza
Fried Ravioli, Baked Rigatoni, Lasagna, Cannelloni, Pizza Sub, and Tiramisu give the menu enough range for groups and non-pizza diners.
03
Regulars' Weekly Rhythm
The Tuesday pizza, Wednesday baked rigatoni, and Thursday stuffed-pizza specials create a simple repeat-visit pattern without bloating the specials surface.
Restaurantica Analysis
How the score breaks down
9.0
Uniqueness
9/10
Bang For Buck
9/10
Food Quality
9/10
Local Reputation
9.5/10
Popularity Factor
9.5/10
The Playbook
How to eat at Chicago Style Pizza
1
Make Stuffed Pizza the Shared Centre
Plan the meal around Stuffed Pizza rather than treating it like a regular pie. The construction and 30-minute bake make it best for guests who are willing to settle in, split slices, and use the rest of the order to keep the first half-hour moving.
2
Start with Fried Ravioli While It Bakes
Fried Ravioli is the easiest opener because it is crisp, compact, and directly useful during the Stuffed Pizza wait. Add Battered Mushrooms or the Appy Platter if the group is larger, but keep the first round simple enough that the pizza still lands as the main event.
3
Use Baked Rigatoni for Pasta Insurance
Baked Rigatoni gives the table a second comfort anchor when not everyone wants to go all-in on deep dish. It also works as the Wednesday value move, which makes it the easiest pasta to remember for regulars who plan by the weekly-special rhythm.
4
Keep Pizza Sub for a Quicker Mood
Pizza Sub is the off-centre move when the Stuffed Pizza wait does not fit the night. It keeps the Chicago thread in the order through garlic butter, pizza sauce, mozzarella, and add-on toppings, but it behaves more like a direct sandwich meal.
5
Close with Tiramisu If Dinner Lingers
Tiramisu is the cleanest dessert finish when the meal has already gone heavy on cheese, sauce, and baked pasta. The mascarpone, espresso, chocolate, rum, and cookie-crumb base give the ending a classic Italian note without needing another large savoury order.
Key Strengths
What this room does best
9.0
Epic Pizza
Stuffed Pizza is the reason to build the meal around this place: a deep-dish pie with sauce, toppings, a cheese-heavy middle, a second dough layer, and a 30-minute bake.
8.0
Comfort Food Specialists
The menu is built for hearty Italian-American comfort: baked rigatoni, lasagna, cannelloni, fried ravioli, battered mushrooms, and tiramisu all support the deep-dish centrepiece.
7.5
Group-Friendly
Stuffed pizza, shareable starters, and baked pasta make the best order easy to split, especially when one guest wants pizza and another wants pasta.
7.5
Budget Dining
The value is easiest to see on repeat visits: Tuesday pizza, Wednesday baked rigatoni, and Thursday stuffed pizza specials give regulars clear nights to plan around.
7.5
The Neighbourhood Anchor
A long-running Upper Sherman address, family-history frame, and unmistakable stuffed-pizza ritual make Chicago Style Pizza feel like a standing Hamilton answer for deep-dish night.
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