Windy City Pizza

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480 Kempsville Rd
Chesapeake, VA 23320

Phone: (757) 410-5550

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Neighborhood: Chesapeake

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Popular Menu Items

• Deep Dish $28.69
• The famous Chicago pie with the sauce on top! Please allow 45 minutes bake time... It's worth the wait!! Add garlic butter to the crust for $1.50
• Thin Crust $11.44+
• Chicago's most popular pizza! Square cut - Signature Blend of 4 Natural Cheeses
• Chicken Wings -dozen $17.77
• Choose from: Mild, Hot, Sweet Baby Ray's BBQ, Sweet Red Chili, Garlic Butter, Garlic Hot or Naked. Served with ranch or bleu cheese
• Pulaski $21.79+
• Our thin crust topped with pepperoni, fresh Italian sausage, smoked ham & bacon
• Italian Beef $11.44
• A Chicago Southside original! Beef "imported" from Chicago, slow cooked in Italian seasonings, thinly sliced & drenched in its own juices, piled high on French bread and toped with sweet peppers. Giardiniera served on request for $0.50. Served with chips - Substitute fries for $1.50

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Reviews for Windy City Pizza

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  4.1 stars - Based on 38 reviews

#103 out of 656 restaurants in Chesapeake

#7 of 55 Pizza in Chesapeake

5 star				9 reviews	24%
4 star				24 reviews	63%
3 star				4 reviews	11%
2 star				0 reviews	0%
1 star				1 review	3%

Top Reviews of Windy City Pizza

04/11/2025 - Caitlin D.
I discovered an incredible restaurant that serves the most amazing dishes. The atmosphere is inviting, and the staff is exceptionally friendly. It's a fantastic experience that I think everyone should try.

05/28/2024 - Aaron C.
Awesome

04/01/2021 - MenuPix User
Horrible customer service and unsanitary. They also make fun of customers.