Cheddar Jalapeño Poppers
Served with Sweet Chili Sauce.
Windy city pizza chesapeake
Chesapeake, VA
480 Kempsville Rd, Chesapeake, VA, 23320-386858 itemsUpdated March 21, 2026
Structured menu data
Appetizers, Wings & Sides
Chicken Wings - 2 Dozen
Choose from: Mild, Hot, Sweet Baby Ray's BBQ, Sweet Red Chili, Garlic Butter, Garlic Hot, Naked. Served with Ranch or Bleu Cheese.
Chicken Wings - ½ Dozen
Choose from: Mild, Hot, Sweet Baby Ray's BBQ, Sweet Red Chili, Garlic Butter, Garlic Hot, Naked. Served with Ranch or Bleu Cheese.
Corn Fritters
Deep-fried and slightly spicy. Filled with Corn, Cream Cheese and Bacon. Served with Ranch.
Fried Pickle Spears
Served with Ranch.
Loaded Fries
A heaping mound of Fries, topped with Real Bacon, Sour Cream and Melted Cheddar Cheese.
Mozzarella Planks
Served with Marinara.
Sampler Platter - Choose 3 or 4
Create your own combo with your choice of Bombs, Planks, Fried Pickles, Fritters, Wings and Poppers.
Seasoned Crinkle-Cut Fries
Southwest Chicken Rolls
Chicken, corn, beans and cheese wrapped in a fried tortilla. Served with sweet chili sauce.
Spicy Sausage Bombs
Large Garlic Italian Sausage Chunks tossed in Hot Sauce. Served with Ranch.
The Original Chicago Pizza Puff
Hand folded Flour Tortilla stuffed with Cheese, Sausage, Pizza Sauce and Spices, then deep-fried to perfection!
Beverages
2 Liter Diet Pepsi
2 Liter Dr. Pepper
2 Liter Mountain Dew
2 Liter Pepsi
Desserts
Cheesecake - Vanilla
Try it topped with Chocolate Syrup.
Chocolate Chunk Cookie
Baked fresh daily.
Specialty Cheesecake
Made in-house. Ask about this month's selection.
Triple Fudge Brownie
Simply the best Brownie on the planet and made in-house!
Dinners
Chicken Parmigiana
2 Boneless Breaded Breasts, smothered in Red Sauce and Mozzarella. Served over Spaghetti. Served with Garlic Bread.
Italian Spaghetti
With your choice of Italian Sausage Link or 2 Meatballs. Served with Garlic Bread.
Lasagna
Layer upon layer of fresh Italian Sausage, Ground Beef, Marinara, Ricotta, Parmesan, and Mozzarella Cheeses. Served with Garlic Bread.
Original, Gluten Free & Deep Dish Pizzas
Brush the crust with real garlic butter
$1.50Deep Dish Pizza - 12" Medium
The Famous Chicago Pie with the Sauce On Top. Please allow up to 45 minutes bake time.
Deep Dish Pizza - 14" Large
The Famous Chicago Pie with the Sauce On Top. Please allow up to 45 minutes bake time.
Deep Dish Pizza - 8" Personal
The Famous Chicago Pie with the Sauce On Top. Please allow up to 45 minutes bake time.
Gluten Free Crust - 14" Medium
Made in a kitchen that may contain trace amounts of Gluten.
Original Thin Crust Pizza - 10" Personal
Chicago's Most Popular Pizza. Square Cut. Signature Blend of 4 Natural Cheeses.
Original Thin Crust Pizza - 14" Medium
Chicago's Most Popular Pizza. Square Cut. Signature Blend of 4 Natural Cheeses.
Original Thin Crust Pizza - 16" Large
Chicago's Most Popular Pizza. Square Cut. Signature Blend of 4 Natural Cheeses.
Premium Deep Dish Pizza
BBQ Chicken and Bacon
Loaded with Diced Chicken Breast, Real Bacon and smothered with Sweet Baby Rays BBQ Sauce.
Heart Attack
Pepperoni, fresh Italian Sausage, Diced Ham and Beef.
Southside Special
Pepperoni, Italian Sausage, Mushrooms, Green Peppers and Onions.
Windy City Special
Crust brushed with Garlic & Oil. Extra portions of fresh Italian Sausage and fresh Baby Spinach.
Salads
Antipasto Salad - Family Size
Genoa Salami, Diced Ham, Black Olives, Banana Peppers, Provolone Cheese and Shredded Mozzarella.
Antipasto Salad - Individual
Genoa Salami, Diced Ham, Black Olives, Banana Peppers, Provolone Cheese and Shredded Mozzarella.
Garden Salad - Add Diced Chicken Breast
Garden Salad - Family Size
Roma Tomatoes, Black Olives, Cheddar Cheese, Croutons.
Garden Salad - Individual
Roma Tomatoes, Black Olives, Cheddar Cheese, Croutons.
Greek Salad - Family Size
Roma Tomatoes, Black Olives, Diced Onions and Feta Cheese.
Greek Salad - Individual
Roma Tomatoes, Black Olives, Diced Onions and Feta Cheese.
Sandwiches
Bread Sticks
Served with Marinara and Garlic Dip.
Cheesy Beef
Italian Beef smothered in Mozzarella. Served with Chips.
Cheesy Bread Sticks
Served with Marinara and Garlic Dip.
Cheesy Garlic Bread
Served with Marinara and Garlic Dip.
Gyros - "Off the Spit"
Beef & Lamb shaved off the Spit, Tzatziki Sauce, Onions and Tomatoes. Served on warm Pita Bread. Served with Chips.
Italian Beef - Chicago Southside Original
Beef "imported" from Chicago, slow cooked in Italian Seasonings, thinly sliced & drenched in its own juices, piled high on French Bread, topped with Sweet Peppers. Giardiniera extra. Served with Chips.
Italian Sausage
A fresh mild Link topped with Red Sauce and Sweet Peppers. Served with Chips.
Meatball
A delicious blend of Beef, Pork, two types of Italian Cheese, Garlic & Spices, topped with Red Sauce and Mozzarella. Served with Chips.
Original Chicago Hot Dog
Authentic Vienna Beef on a Poppy Seed Bun topped with Mustard, Relish, Onions, Tomatoes, Pickle Spear, Sport Pepper and Celery Salt. Served with Chips.
The "Ditka" Combo - "Da Coach's Favorite!!!"
Italian Beef piled high on top of an Italian Sausage Link. Served with Chips.
Specialty Pizzas
The "Cicero"
Pepperoni, Fresh Italian Sausage, Mushrooms, Bell Peppers and Onions.
The "Clark St."
Fresh Spinach, Tomato Slices, Olives and White Garlic Sauce.
The "Maxwell St."
Seasoned Steak, Bell Peppers, Onions, 2 Layers of Cheese and White Garlic Sauce.
The "Michigan Ave."
Mushrooms, Bell Peppers, Onions and Black Olives.
The "Pulaski"
Pepperoni, Fresh Italian Sausage, Diced Ham and Bacon.
The "Stony Island"
Sweet Baby Rays BBQ Sauce, Chicken (NO, it's not fried) and Bacon.