Windy city pizza chesapeake Menu (2025 Update)
Welcome to Windy City Pizza Chesapeake, where authentic Chicago-style pizza meets a cozy atmosphere. Located at 480 Kempsville Rd, Chesapeake, VA, this spot is renowned for its deep-dish pizzas that ooze flavor with every slice. Customers rave about the Italian Beef sandwich, slow-cooked to perfection, and the crispy chicken wings that come in a variety of sauces.
Start your meal with a plate of loaded fries or their unique take on mozzarella sticks, served deep-fried and delightfully crispy. The main event, however, is undoubtedly the deep-dish pizza; a delightful feast that's enough to satisfy multiple diners.
With friendly staff and excellent service, Windy City Pizza Chesapeake promises an unforgettable dining experience. So gather your friends for a satisfying meal that transports you straight to Chicago!
Sandwiches
Chicago Hot Dog
Authentic Vienna beef "dragged through the garden" on a a poppy seed bun. For our East coast friends, the garden includes: mustard, relish, onions, tomatoes, pickle spear, sport peppers and celery salt. Served with chips - Substitute fries for 1.50
Gyros
Beef & lamb shaved fresh off the spit, tzatziki sauce, onions & tomatoes on warn pita bread. Add feta for 1. Served with chips - Substitute fries for 1.50
Italian Sausage Sand
A fresh mild link topped with red sauce and sweet peppers. Served with chips - Substitute fries for 1.50
Cheesy Beef
Italian beef smothered in mozzarella cheese. Served with chips - Substitute fries for 1.50
Chicago Hot Dogs (2)
The "Ditka" Combo
Da Coach's Favorite!! Italian beef piled high on top of an italian sausage link. Served with chips - Substitute fries for 1.50
Chicken Parm Sand
Fried split chicken breast smothered in red sauce and topped with mozzarella cheese. Served with chips - Substitute fries for 1.50
Meatball Sand
A delicious blend of beef, pork, two types of Italian cheeses, garlic & spices topped with red sauce & mozzarella. Served with chips - Substitute fries for 1.50
Italian Beef
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
Chicken Parm Dinner
Two boneless breaded chicken breasts, smothered in red sauce and topped with mozzarella cheese. Served over spaghetti... includes garlic bread
Lasagna
Layer upon layer of fresh Italian sausage, ground beef, ricotta, parmesan & mozzarella cheese... includes garlic bread
Spaghetti
With your choice of Italian sausage or two meatballs... includes garlic bread
Dinners
Appetizers
Crinkle Cut Fries
Chicken Wings -Dozen
Choose from: Mild, Hot, Sweet Baby Ray's BBQ, Sweet Red Chili, Garlic Butter, Garlic Hot or Naked. Served with ranch or bleu cheese
Lays Potato Chips
Cheesy Breadsticks
Served with marinara
Sampler Platter
Create your own combo with your choice of Planks, Poppers, Pickles, Fritters, Sausage Bombs & Wings . Choose 3 or 4
Corn Fritters
Deep fried and slightly spicy. Filled with corn, cream cheese & bacon. Served with ranch
Mozzarella Planks
Served with marinara
Cheesy Garlic Bread
Sausage Bombs
Large garlic Italian sausage chunks tossed in hot sauce and served with ranch
Fried Pickle Spears
Served with ranch
Buffalo Chicken Dip
Made in house! Creamy buffalo chicken dip(shredded chicken, buffalo sauce, ranch, cheddar and cream cheese) served warm with seasoned pita chips
Chicken Wings 2 Dozen
Pizza Puff
Hand-folded flour tortilla stuffed with cheese, sausage, pizza sauce and spices, then deep fried to perfection!
Southwest Rolls
Cheddar Jalapeno Poppers
Serve with sweet chili sauce
Breadsticks
Served with marinara
Chicken Wings- Half Dozen
Choose from: Mild, Hot, Sweet Baby Ray's BBQ, Sweet Red Chili, Garlic Butter, Garlic Hot or Naked. Served with ranch or bleu cheese
Loaded Fries
A heaping mound of fries topped with real bacon, melted cheddar cheese & sour cream
Garlic Bread
Other Drink
2 Liter Pepsi
Bottled Water
2 Liter Diet Pepsi
2 Liter Dr Pepper
2 Liter Mountain Dew
Beverages
Dessert
Specialty Cheesecake
Made in house.
Vanilla Cheesecake
Cake
Brownie
Cookie
Heart Attack
Our deep dish crust topped with pepperoni, fresh Italian sausage, diced ham & beef
Windy City Special
Our deep dish crust brushed with garlic & oil. Extra portions of fresh Italian sausage & fresh baby spinach
Pulaski
Our thin crust topped with pepperoni, fresh Italian sausage, smoked ham & bacon
Cicero
Our thin crust topped with pepperoni, fresh Italian sausage, mushrooms, bell peppers & onions
Michigan Ave
Our thinl crust topped with mushrooms, bell peppers, onions & black olives
Thin Crust
Chicago's most popular pizza! Square cut - Signature Blend of 4 Natural Cheeses
Deep Dish
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
BBQ Chicken & Bacon
Our deep dish crust loaded with diced chicken breast, real bacon & smothered with Sweet Baby Ray's BBQ sauce
Maxwell St.
Our thin crust topped with white sauce, seasoned steak, bell peppers, onions & plenty of cheese
Gluten-Free
Clark St.
A thin crust white pizza - White sauce, fresh spinach, tomato slices & olives
Stony Island
Our thin crust topped with Sweet Baby Ray's BBQ Sauce, chicken & bacon
Southside Special
Our deep dish crust topped with pepperoni, Italian sausage, mushrooms, green peppers & onions
Pizza
Salads
Individual Greek Salad
Roma tomatoes, black olives, diced onions & feta cheese with your choice of dressing
Family Greek Salad
Individual Antipasto Salad
Genoa salami, diced ham, black olives, banana peppers, provolone cheese & shredded mozzarella with your choice of dressing.
Family Antipasto Salad
Individual Garden Salad
Roma tomatoes, black olives, cheddar cheese & croutons with your choice of dressing. Add diced chicken for 2/6