Windy city pizza chesapeake Menu – Chesapeake, VA

Type : Pizza restaurant

Location : Chesapeake, VA

Based on 836 reviews, the restaurant has received a rating of 4.4 stars. Price $$

✔️ Dine-in ✔️ Takeout ✔️ No-contact delivery

Windy city pizza chesapeake 23320

Address:
480 Kempsville Rd, Chesapeake, VA 23320

Phone: (757) 410-5550

Website: http://windycityvb.com/

Hours

Wednesday 11 AM–8:30 PM
Thursday 11 AM–8:30 PM
Friday 11 AM–9:30 PM
Saturday 11 AM–9:30 PM
Sunday 11 AM–9:30 PM
Monday 11 AM–8:30 PM
Tuesday 11 AM–8:30 PM

Menu

Appetizers
Breadsticks
Served with marinara
$4.95
Cheesy Breadsticks
Served with marinara
$6.84
Garlic Bread $3.95
Cheesy Garlic Bread $5.95
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
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
Sampler Platter
Create your own combo with your choice of Planks, Poppers, Pickles, Fritters, Sausage Bombs & Wings . Choose 3 or 4
$11.95
Sausage Bombs
Large garlic Italian sausage chunks tossed in hot sauce and served with ranch
$6.95
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
$6.95
Mozzarella Planks
Served with marinara
$7.95
Loaded Fries
A heaping mound of fries topped with real bacon, melted cheddar cheese & sour cream
$8.95
Crinkle Cut Fries $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
Seafood Dip
Real crab & shrimp (not surimi) blended with aged parmesan & spices. Served with fried pita chips
$9.95
Pizza Puff
Hand-folded flour tortilla stuffed with cheese, sausage, pizza sauce and spices, then deep fried to perfection!
$4.95
Lays Potato Chips $1.45
Pizza
Thin Crust
Chicago’s most popular pizza! Square cut – Signature Blend of 4 Natural Cheeses
$9.95
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
$23.95
Gluten-Free $15.95
Windy City Special
Our deep dish crust brushed with garlic & oil. Extra portions of fresh Italian sausage & fresh baby spinach
$29.95
BBQ Chicken & Bacon
Our deep dish crust loaded with diced chicken breast, real bacon & smothered with Sweet Baby Ray’s BBQ sauce
$28.95
Southside Special
Our deep dish crust topped with pepperoni, Italian sausage, mushrooms, green peppers & onions
$31.95
Heart Attack
Our deep dish crust topped with pepperoni, fresh Italian sausage, diced ham & beef
$29.95
Pulaski
Our thin crust topped with pepperoni, fresh Italian sausage, smoked ham & bacon
$17.95
Michigan Ave
Our thinl crust topped with mushrooms, bell peppers, onions & black olives
$16.95
Cicero
Our thin crust topped with pepperoni, fresh Italian sausage, mushrooms, bell peppers & onions
$18.95
Clark St
A thin crust white pizza – White sauce, fresh spinach, tomato slices & olives
$16.95
Stony Island
Our thin crust topped with Sweet Baby Ray’s BBQ Sauce, chicken & bacon
$16.95
Maxwell St
Our thin crust topped with white sauce, seasoned steak, bell peppers, onions & plenty of cheese
$16.95
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 $17.95
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 $21.95
Individual Greek Salad
Roma tomatoes, black olives, diced onions & feta cheese with your choice of dressing
$6.95
Family Greek Salad $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
$9.95
Cheesy Beef
Italian beef smothered in mozzarella cheese. Served with chips – Substitute fries for $1.50
$10.95
Italian Sausage Sand
A fresh mild link topped with red sauce and sweet peppers. Served with chips – Substitute fries for $1.50
$7.95
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
$14.95
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
$8.95
Chicken Parm Sand
Fried split chicken breast smothered in red sauce and topped with mozzarella cheese. Served with chips – Substitute fries for $1.50
$8.95
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
$9.95
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
$5.45
Chicago Hot Dogs (2) $9.95
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
$14.95
Dessert
Vanilla Cheesecake $5.95
Specialty Cheesecake
Made in house.
$6.95
Stawberries $1.00
Chocolate Syrup $0.50
Oreo Bar $6.95
Cookie $2.25
Brownie $3.75
Beverages
Bottled Water $2.25
Other Drink $3.50
2 Liter Pepsi $3.75
2 Liter Diet Pepsi $3.75
2 Liter Mountain Dew $3.75
2 Liter Dr Pepper $3.75

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Menu Photos

Photo Gallery

Reviews

NC Traveler
I liked the reviews I read, so we gave Windy City a shot. We ordered three pizzas for pick-up (one of their specialty pizzas, a Hawaiian, and a pepperoni – all well done). The pizza was just not good, and I really don’t like giving bad reviews. The ingredients were average, the crust was the worse part. The dough was dense, with little taste and absolutely no crispiness to it. They only had one style of dough thickness, no thin crust option. For the price I would not consider giving this place another shot. On a good note, the staff was very nice, the place was clean, and looks like a good place to eat dinner.

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Tim Ainsley
Been here quite a few times over the years and the pizza has always been top notch. I guess they have a lot of new people in the kitchen now as this was about the worst pizza I’ve ever had. They only put half the toppings I ordered on our pizzas, but still left them on the bill. If the kids they have in the kitchen would put as much effort into making the pizzas as they did into looking at their phones maybe the food would be better. It will be awhile before I go back there. Frozen pizzas from the grocery store would be better, and wouldn’t cost $60

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Makael George
Love their deep dish pizza! The sauce and cheese is fantastic absolutely worth checking out.

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James Mariner
Southside pizza was Amazing! Our waitress was just as awesome as our food!

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George Brooks
First time visiting this location. Had a craving for a meatball sub. Decided to get some wings also. Having grown up in the northeast in Connecticut I have a high standard for meatball subs or grinders. This was the worse one I’ve ever had. The meatballs were ok but almost no sauce and no cheese an no taste. You don’t want too much sauce, but it shouldn’t be dry. It’s like they ran out of cheese and sauce. Look how little cheese was on it!! The bread was terrible also. I’ve come to expect less here in Virginia when it comes to Italian bread. Not only was it spongy but it was 5 inches long. The shortest meatball sub I’ve ever had. I’ve had good experiences at the other Windy City location. This was terrible. The Buffalo wings were tiny, had no taste. It was like they tossed them in some Texas Pete and called it good. I’ll give them another chance but this was terribly disappointing.

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Nicki Hepler
Service was great, we were the only table there. I have to say I have had their pizza on 3 other occasions all were great. This time however I should have just stayed home and had Dijiornos. Honestly this may have been the worst pizza I have ever had. I even through away the leftovers.

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Sam Lopez
This location tends to be closer to my friend’s house. I’d wanted him to try this Chicago-style deep dish pizza. So I’d ordered the loaded cheese fries as an appetizer. And put in the order for the Heart Attack deep dish. I only ate one slice. I’m not trying to actually have a heart attack. Ah man, reminds me of WCP of VB. The same stuff at a different location. Just like home! It’s so good!

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Scott Tyree
This place is awesome. The pizza was kind of expensive. I literally got one speciality Chicago style and spent over 30 dollars. But last time I got chanellos it was like over 20 a pie. At any rate it was well worth the price. The pizza I received had to weigh like 3 to 5 pounds and what was inside was ooey gooey mozzarella. A generous portion of marinara and no skimping on the toppings. It took me like 3 days to finish it. a meal is maybe two slices. Highly recommend this place. You’re missing out if you don’t try it

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David Chaney
Had better microwave wings. I was told my food would be ready in a few. After waiting 25 minutes I asked how much longer to a different person. They handed me a medium warm pizza and cold wings. As I was leaving they started laughing. Service and atmosphere was worse than the wings. Pizza was above average but not great. If you like pizza served by Marjorie Taylor Greene and Lauren Boebert this is it.

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Steve Waddell
My wife and I came here on one of our Pizza Safaris, which is where we try a new pizza restaurant. Normally thin crust pizza fans, we did enjoy Giiordanos on a trip to Florida many years ago which also has deep dish.

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