Windy City Pizza
Windy city pizza chesapeake, 480 Kempsville Rd, Chesapeake, VA 23320, USAOpens 11:00 AM
Order for later
Featured Items
#1 Most liked
Thin Crust
$9.95+
#2 Most liked
Deep Dish
$12.95+
#3 Most liked
Southside Special
$16.95+
Heart Attack
$16.95+
Cicero
$15.95+
Pulaski
$14.95+
Chicken Wings -dozen
$15.45
Windy City Special
$16.95+
Mozzarella Planks
$7.95
Chicago Hot Dogs (2)
$10.95
Gluten-Free
$15.95+
Italian Beef
$10.95
Cheesy Garlic Bread
$5.95
Buffalo Chicken Dip
$8.95
Pizza Puff
$5.95
Cheesy Beef
$11.95
Fried Pickle Spears
$7.95
Maxwell St.
$13.95+
Crinkle Cut Fries
$3.95
Chicago Hot Dog
$5.95
Gyros
$10.95
Lasagna
$12.95
Loaded Fries
$8.95
Sausage Bombs
$6.95
Corn Fritters
$7.95
Full Menu
11:00 am - 7:55 pmMost Ordered
The most commonly ordered items and dishes from this store
Thin Crust
#1 Most liked
Chicago's most popular pizza! Square cut - Signature Blend of 4 Natural Cheeses
$9.95+•98% (77)
Deep Dish
#2 Most liked
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
$12.95+•96% (51)
Southside Special
#3 Most liked
Our deep dish crust topped with pepperoni, Italian sausage, mushrooms, green peppers & onions
$16.95+•96% (26)
Mozzarella Planks
Served with marinara
$7.95•100% (9)
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
$15.45•100% (8)
Cicero
Our thin crust topped with pepperoni, fresh Italian sausage, mushrooms, bell peppers & onions
$15.95+
Pulaski
Our thin crust topped with pepperoni, fresh Italian sausage, smoked ham & bacon
$14.95+•100% (17)
Heart Attack
Our deep dish crust topped with pepperoni, fresh Italian sausage, diced ham & beef
$16.95+•100% (10)
Chicago Hot Dogs (2)
Two Chicago-style hot dogs served with options of chips, fries, loaded fries, garden salad, Greek salad, or antipasto as side modifications.
$10.95•100% (8)
Cheesy Garlic Bread
Savory Garlic Bread Loaded with Melted Cheese
$5.95•100% (9)
Appetizers
Breadsticks
Served with marinara
$4.95
Cheesy Breadsticks
Served with marinara
$5.95
Garlic Bread
Crisp, buttery toasted bread infused with aromatic garlic and herbs.
$3.95
Cheesy Garlic Bread
Savory Garlic Bread Loaded with Melted Cheese
$5.95•100% (9)
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
$7.95•88% (9)
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
$15.45•100% (8)
Chicken Wings 2 dozen
Chicken wings in choice of sauce: Mild, Hot, BBQ, Sweet Chili, Garlic Butter, Garlic Hot, or plain. Served with Ranch or Bleu Cheese.
$29.95
Pizza Puff
Hand-folded flour tortilla stuffed with cheese, sausage, pizza sauce and spices, then deep fried to perfection!
$5.95•87% (8)
Cheddar Jalapeno Poppers
Serve with sweet chili sauce
$7.95
Corn Fritters
Deep fried and slightly spicy. Filled with corn, cream cheese & bacon. Served with ranch
$7.95
Fried Pickle Spears
Served with ranch
$7.95
Mozzarella Planks
Served with marinara
$7.95•100% (9)
Sausage Bombs
Large garlic Italian sausage chunks tossed in hot sauce and served with ranch
$6.95
Sampler Platter
Create your own combo with your choice of Planks, Poppers, Pickles, Fritters, Sausage Bombs & Wings . Choose 3 or 4
$11.95+
Loaded Fries
A heaping mound of fries topped with real bacon, melted cheddar cheese & sour cream
$8.95
Onion Rings
Sliced onions are typically breaded and deep-fried until golden brown, creating a crispy appetizer.
$4.95
Crinkle Cut Fries
Savory crinkle-cut fries, golden and crisply fried to perfection.
$3.95
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
$8.95•100% (6)
Pizza
Thin Crust
#1 Most liked
Chicago's most popular pizza! Square cut - Signature Blend of 4 Natural Cheeses
$9.95+•98% (77)
Deep Dish
#2 Most liked
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
$12.95+•96% (51)
Gluten-Free
Gluten-free pizza with customizable toppings. Available in 14" medium.
$15.95+•100% (7)
Windy City Special
Our deep dish crust brushed with garlic & oil. Extra portions of fresh Italian sausage & fresh baby spinach
$16.95+
BBQ Chicken & Bacon
Our deep dish crust loaded with diced chicken breast, real bacon & smothered with Sweet Baby Ray's BBQ sauce
$15.95+
Southside Special
#3 Most liked
Our deep dish crust topped with pepperoni, Italian sausage, mushrooms, green peppers & onions
$16.95+•96% (26)
Heart Attack
Our deep dish crust topped with pepperoni, fresh Italian sausage, diced ham & beef
$16.95+•100% (10)
Pulaski
Our thin crust topped with pepperoni, fresh Italian sausage, smoked ham & bacon
$14.95+•100% (17)
Michigan Ave
Our thinl crust topped with mushrooms, bell peppers, onions & black olives
$13.95+
Cicero
Our thin crust topped with pepperoni, fresh Italian sausage, mushrooms, bell peppers & onions
$15.95+
Clark St.
A thin crust white pizza - White sauce, fresh spinach, tomato slices & olives
$13.95+
Stony Island
Our thin crust topped with Sweet Baby Ray's BBQ Sauce, chicken & bacon
$13.95+
Maxwell St.
Our thin crust topped with white sauce, seasoned steak, bell peppers, onions & plenty of cheese
$13.95+•100% (7)
Salads
Individual Garden Salad
Roma tomatoes, black olives, cheddar cheese & croutons with your choice of dressing. Add diced chicken for $2/$6
$5.95
Family Garden Salad
Fresh mixed greens with choice of two dressings: ranch, bleu cheese, Italian, balsamic, or Greek. Option for no dressing available.
$18.95
Individual Antipasto Salad
Genoa salami, diced ham, black olives, banana peppers, provolone cheese & shredded mozzarella with your choice of dressing.
$6.95
Family Antipasto Salad
Family-sized antipasto salad with choice of two dressings: ranch, bleu cheese, fat-free Italian, balsamic vinaigrette, Greek, or no dressing option.
$21.95
Individual Greek Salad
Roma tomatoes, black olives, diced onions & feta cheese with your choice of dressing
$6.95
Family Greek Salad
Mixed greens, olives, feta, cucumbers, tomatoes. Choice of 2 dressings: ranch, bleu cheese, Italian, balsamic, Greek, or no dressing.
$21.95
Sandwiches
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
$10.95•85% (7)
Cheesy Beef
Italian beef smothered in mozzarella cheese. Served with chips - Substitute fries for $1.50
$11.95
Italian Sausage Sand
A fresh mild link topped with red sauce and sweet peppers. Served with chips - Substitute fries for $1.50
$8.95
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
$15.95
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
$10.95
Chicken Parm Sand
Fried split chicken breast smothered in red sauce and topped with mozzarella cheese. Served with chips - Substitute fries for $1.50
$10.95
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
$11.95
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
$5.95
Chicago Hot Dogs (2)
Two Chicago-style hot dogs served with options of chips, fries, loaded fries, garden salad, Greek salad, or antipasto as side modifications.
$10.95•100% (8)
Dinners
Spaghetti
With your choice of Italian sausage or two meatballs... includes garlic bread
$13.95
Lasagna
Layer upon layer of fresh Italian sausage, ground beef, ricotta, parmesan & mozzarella cheese... includes garlic bread
$12.95
Chicken Parm Dinner
Two boneless breaded chicken breasts, smothered in red sauce and topped with mozzarella cheese. Served over spaghetti... includes garlic bread
$15.95
Dessert
Vanilla Cheesecake
A creamy cheesecake infused with vanilla on a buttery graham cracker crust.
$6.95
Cake
$7.95
Cookie
Deliciously baked, classic sweet treat perfect with milk or coffee.
$2.95
Brownie
$3.95•75% (8)
Beverages
Other Drink
Soda: Typically includes options like Coke, Diet Coke, Sprite, Root Beer, and Mountain Dew.
$3.50
2 Liter Pepsi
Refreshing 2-Liter Pepsi: Crisp, Effervescent Classic Cola
$3.95
2 Liter Diet Pepsi
A 2-liter bottle of Diet Pepsi, offering a crisp and refreshing pop of sweet, fizzy bubbles, typically without the calories.
$3.95
2 Liter Mountain Dew
A 2-liter bottle of Mountain Dew, offering a unique citrus flavor.
$3.95
2 Liter Dr Pepper
A 2-liter bottle of Dr. Pepper soda, featuring a distinct combination of 23 unique flavors for a refreshing experience.
$3.95
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