Family-owned and steeped in tradition, Bartoli’s keeps things laid-back and delicious at both their Roscoe Village and West Town locations. Start with fresh, flavorful bruschetta before diving into their award-winning deep-dish, known for its signature zingy tomato sauce. If you’re up for sharing (good luck), split Nonna Bertoli’s Famous Meatball Sub with a side of crispy beer-battered fries. But the tiramisu? That’s all yours.

There’s a reason you’ll find a Lou Malnati’s on practically every corner in Chicago—their deep-dish recipe is pure magic. The crispy, buttery crust, chunky tomato sauce, and perfectly seasoned flat sausage, all nestled under a blanket of rich Wisconsin mozzarella, make every bite unforgettable. Step into one of their funky, eclectic dining rooms, grab a slice and taste why they’ve been a staple for over 70 years.

This cozy, minimalist joint is always packed, so reservations and pre-orders are a must. Every pizza here is named after a famous George, and the pies are baked to perfection with a light, focaccia-style crust. Go bold with Michael’s S&M, loaded with spaghetti and meatballs, or keep it fresh with Orwell’s Farm, a veggie lover’s dream.

Pequod’s isn’t just a cult favorite—it’s been name-dropped by The Food Network, FX’s The Bear, and pretty much every Chicago pizza list. Their pan-style deep dish is famous for its caramelized crust, and the sizzling scent of garlic bread and molten cheese hits the second you walk under their neon marquee. Make a reservation or order ahead, then grab a drink at Whale Tale next door while you wait.

Milly’s keeps it casual and a little retro, but the pizza? It’s anything but old-school. The Updog is a standout with fresh Kumato tomatoes, pepperoni, and sausage, while Untitled #1 brings the heat with Glory’s tomatoes, jalapeños, and mozz. For an extra kick, drizzle on Mr. Bing’s Chili Crunch—it’ll wake up your taste buds in the best way. Heads up: they only make a limited number of pizzas each day, so order ahead.

Don’t let the no-frills vibe fool you—Art of Pizza is serious about their pies. Their pan-stuffed creations, made with vine-ripened tomatoes and Wisconsin cheese, hold their own in Chicago’s competitive pizza scene. Stick with classics like sausage and pepperoni, or mix things up with Art’s Southwestern, a BBQ-based specialty. Want something extra? Try the breaded zucchini or go all in with the chicken parmigiana.

Labriola brings a little extra flair to the Chicago pizza scene. On a sunny day, grab a seat on the patio and sip an Almafi Coastin’ (tequila-based) or Tropic Thunder (a tropical twist). The pizzas here range from fluffy, Sicilian-style deep dish with a crisp, airy crust to prosciutto and arugula-topped Artisan pizzas on thin ciabatta dough. Don’t skip the pasta—served in elegant blue china with crispy smashed potatoes and charred broccolini on the side.

A Chicago staple since 1970, Tortorice’s is known for its deeply caramelized crust and casual, easygoing atmosphere. Grab a massive meatball sandwich, order at the counter, and take in the Italian villa murals while you wait. If you’re feeling adventurous, try the loaded antipasto salad, jumbo wings, or XL fried calamari rings. But let’s be real—you’re here for the pizza, and every crispy bite is worth it.

Pizano’s has been winning over pizza lovers for 30+ years, and with five locations, it’s easier than ever to get your fix. Their buttery, flaky crust is a must-try, best enjoyed at a red-and-white checkered table with a glass of red wine. Start with a bowl of tortellini soup, grab a carb-free or gluten-free option if that’s your thing, or take home a frozen Hey Hey Jack Brickhouse Special for later.