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Windy city pizza chesapeake — Restaurant in Chesapeake

Name
Windy city pizza chesapeake
Description
Nearby attractions
Fun Forest Playground
900 City Park Dr, Chesapeake, VA 23320
Nearby restaurants
The Egg Bistro
501 Kempsville Rd, Chesapeake, VA 23320
Ang's Sushi Bistro
501 Kempsville Rd, Chesapeake, VA 23320
GOLDEN STAR
473 Kempsville Rd #104, Chesapeake, VA 23320
Atlas Pizza
517 Kempsville Rd Suite A And B, Chesapeake, VA 23320
Huddle House
473 Kempsville Rd #110, Chesapeake, VA 23320
Zeke's
517 Kempsville Rd Suite E, Chesapeake, VA 23320
China 1 Chinese Restaurant
517 Kempsville Rd, Chesapeake, VA 23320
Rita's Italian Ice & Frozen Custard
Greenbrier Shoppes, 501 Kempsville Rd, Chesapeake, VA 23320, United States
Nearby hotels
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Keywords
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Windy city pizza chesapeake things to do, attractions, restaurants, events info and trip planning
Windy city pizza chesapeake
United StatesVirginiaChesapeakeWindy city pizza chesapeake

Basic Info

Windy city pizza chesapeake

480 Kempsville Rd, Chesapeake, VA 23320
4.3(513)
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spot

Ratings & Description

Info

attractions: Fun Forest Playground, restaurants: The Egg Bistro, Ang's Sushi Bistro, GOLDEN STAR, Atlas Pizza, Huddle House, Zeke's, China 1 Chinese Restaurant, Rita's Italian Ice & Frozen Custard
logoLearn more insights from Wanderboat AI.
Phone
(757) 410-5550
Website
windycityvb.com

Plan your stay

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Featured dishes

View full menu
dish
Individual Greek Salad
dish
Family Greek Salad
dish
Heart Attack
dish
Cicero
dish
Windy City Special
dish
Brownie
dish
Lasagna
dish
Spaghetti
dish
Chicken Parm Dinner
dish
Chicago Hot Dogs (2)
dish
Italian Beef
dish
The "Ditka" Combo
dish
Italian Sausage Sand
dish
Chicago Hot Dog
dish
Gyros
dish
Corn Fritters
dish
Pizza Puff
dish
Cheesy Garlic Bread
dish
Breadsticks
dish
Fried Pickle Spears
dish
Mozzarella Planks
dish
Chicken Wings -Dozen
dish
Loaded Fries
dish
Crinkle Cut Fries

Reviews

Nearby attractions of Windy city pizza chesapeake

Fun Forest Playground

Fun Forest Playground

Fun Forest Playground

4.8

(773)

Open 24 hours
Click for details

Things to do nearby

Set Apart: A worship night for singles
Set Apart: A worship night for singles
Fri, Dec 12 • 7:00 PM
1101 Volvo Parkway, Chesapeake, VA 23320
View details
CSI Security- Securing Sacred Spaces 12/13/25
CSI Security- Securing Sacred Spaces 12/13/25
Sat, Dec 13 • 9:00 AM
4316 Bruce Road, Chesapeake, VA 23321
View details
NEON Holiday Market 2025
NEON Holiday Market 2025
Sat, Dec 13 • 12:00 PM
776 Granby Street, Norfolk, VA 23510
View details

Nearby restaurants of Windy city pizza chesapeake

The Egg Bistro

Ang's Sushi Bistro

GOLDEN STAR

Atlas Pizza

Huddle House

Zeke's

China 1 Chinese Restaurant

Rita's Italian Ice & Frozen Custard

The Egg Bistro

The Egg Bistro

4.7

(2.4K)

Click for details
Ang's Sushi Bistro

Ang's Sushi Bistro

4.5

(181)

Click for details
GOLDEN STAR

GOLDEN STAR

4.2

(163)

Click for details
Atlas Pizza

Atlas Pizza

4.4

(259)

Click for details
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Posts

Tanjara HolleyTanjara Holley
I've purchased a pizza from Windy City 2 times before today, put it in my back seat, drove home and had no issues. I just purchased a deep dish pizza, placed it in my back seat, drove home and opened the box to a soggy mess. I called the restaurant explained the situation and was asked if I wanted to speak to a manager (Callie? Kelly?), she explained that it probably shifted during transport, which I told her made sense. I picked up the pizza right as it came out the oven, so it hadn't set yet. She said the pizzas can be fragile (due to the sauce on top). My issue is how rude and dry she was about the situation- Kallie's response being "ok... what do you want me to do about it?" I told her being given a warning before leaving the store, whether it was verbal or a warning on the box, to place the pizza on the FLOOR instead of my back seat would have been nice. I thanked her for providing clarity and suggested that I come back to the store with the pizza and have it re-made or be given a refund. Kayley says "no. I'm not doing that", leaving me to realize that the "what do you want me to do about it?" question was rhetorical, and instead, a way to add some humor to what I'm sure is a very exciting life of serving pizzas. I called back up to the store to ask for her name so I could write this review and the owner, John, came to the phone and explained that Kally is his wife and asked why she needed to tell me to travel with the pizza laying flat (cue laughter in the background). He hung up as I started telling him how surprised I am at how rude they were being. John is running what seems to be a relatively successful business, which takes a brain to do, so I doubt he actually thinks I drove with my pizza in hand or anywhere other that what I originally said- in my empty back seat. My experience before today has always been pleasant, because I've only ever dealt with the young woman on the register, which is why I was shocked to know that the people who actually run the place don't care how they speak to the people who pay them.
TERRY TIBBSGriffinTERRY TIBBSGriffin
I visited this location on Sunday August 22nd. First of all I now live in VA. but I grew up in Chicago. I discovered Windy City when it was fairly new. I was so excited to have some Chicago real deep dish pizza. I usually drive to the VA. Beach location, which is an hour or more. I decided this particular day I would try the Chesapeake store, a little less driving. ALWAYS stick to what you know so there will be no disappointment. I have been to the VA Beach location on several occasions. The problem was I ordered 2 pizza's drove almost an hour to get the pizza. Chicago deep dish pizza has sauce on top, sausage or whatever the meat is all across the pizza not skimpy, then the cheese. One pizza had sausage and the other had half cheese and half pepperoni. I have included a picture of what was left of the pizza. We literally had to look for the sausage. I called the VA Beach store on Monday to express my disappointment. The manager on duty was Tasha. She ask me to email her a picture since I still had some leftover. She said she would get back to me after she had a chance to look at the email. I waited 2 days she never responded. I called again by the third day because no one reached out. I spoke to Mike who said that's not my store I need to reach out to his brother who runs that store. He said he forwarded the email to his brother. I never heard from anyone at that store. I feel if the owner has been sent the email he should reach out to me the customer. I'm very disappointed in their lack of interest towards showing care or concern about the need of their customers. I refer people to Windy city pizza all the time, but they showed no concern at all about my situation. I have an issue with merchants who don't care if the customer is happy. If you look at the picture you will see no sausage. Normally the meat is plentiful. The picture is the sausage pizza. The sausage was very skimpy to none.
Myan KennonMyan Kennon
Wanted to see if I could get a REAL CHICAGO STYLE PIZZA, in the 757. And I think I found it! We got to the restaurant within an hour after they opened on a Saturday, and it was not busy at all! We were sat immediately and decided to out in an order for an appetizer. We chose the buffalo chicken dip. The dip was served with pita bread and they were the perfect texture. If you’re like me and don’t like your bread burnt or super crisp, then you would like the pita bread. Fluffy. The dip was amazing and the perfect amount of buffalo! Wasn’t too heavy either. The dip was 8.95. Now onto the pizza: it was a deep dish, Chicago style pizza. We added sausage as a topping, and it was so good! I honestly couldn’t speak highly enough of this pizza. It was so good! It was 22.99 before the topping, which was an extra 1.75. The price is up there for a pizza, but honestly it was worth it because the pizza is so filling, it would comfortably feed 3-4 people. My husband and I ended up taking some to our friends who couldn’t make it, cause we couldn’t finish it at the restaurant. If you’re trying to find a good pizza place to eat with some friends, this is it! Service was fast and our waitress was very friendly! Cash and card is accepted!
See more posts
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I've purchased a pizza from Windy City 2 times before today, put it in my back seat, drove home and had no issues. I just purchased a deep dish pizza, placed it in my back seat, drove home and opened the box to a soggy mess. I called the restaurant explained the situation and was asked if I wanted to speak to a manager (Callie? Kelly?), she explained that it probably shifted during transport, which I told her made sense. I picked up the pizza right as it came out the oven, so it hadn't set yet. She said the pizzas can be fragile (due to the sauce on top). My issue is how rude and dry she was about the situation- Kallie's response being "ok... what do you want me to do about it?" I told her being given a warning before leaving the store, whether it was verbal or a warning on the box, to place the pizza on the FLOOR instead of my back seat would have been nice. I thanked her for providing clarity and suggested that I come back to the store with the pizza and have it re-made or be given a refund. Kayley says "no. I'm not doing that", leaving me to realize that the "what do you want me to do about it?" question was rhetorical, and instead, a way to add some humor to what I'm sure is a very exciting life of serving pizzas. I called back up to the store to ask for her name so I could write this review and the owner, John, came to the phone and explained that Kally is his wife and asked why she needed to tell me to travel with the pizza laying flat (cue laughter in the background). He hung up as I started telling him how surprised I am at how rude they were being. John is running what seems to be a relatively successful business, which takes a brain to do, so I doubt he actually thinks I drove with my pizza in hand or anywhere other that what I originally said- in my empty back seat. My experience before today has always been pleasant, because I've only ever dealt with the young woman on the register, which is why I was shocked to know that the people who actually run the place don't care how they speak to the people who pay them.
Tanjara Holley

Tanjara Holley

hotel
Find your stay

Affordable Hotels in Chesapeake

Find a cozy hotel nearby and make it a full experience.

Get the Appoverlay
Get the AppOne tap to find yournext favorite spots!
I visited this location on Sunday August 22nd. First of all I now live in VA. but I grew up in Chicago. I discovered Windy City when it was fairly new. I was so excited to have some Chicago real deep dish pizza. I usually drive to the VA. Beach location, which is an hour or more. I decided this particular day I would try the Chesapeake store, a little less driving. ALWAYS stick to what you know so there will be no disappointment. I have been to the VA Beach location on several occasions. The problem was I ordered 2 pizza's drove almost an hour to get the pizza. Chicago deep dish pizza has sauce on top, sausage or whatever the meat is all across the pizza not skimpy, then the cheese. One pizza had sausage and the other had half cheese and half pepperoni. I have included a picture of what was left of the pizza. We literally had to look for the sausage. I called the VA Beach store on Monday to express my disappointment. The manager on duty was Tasha. She ask me to email her a picture since I still had some leftover. She said she would get back to me after she had a chance to look at the email. I waited 2 days she never responded. I called again by the third day because no one reached out. I spoke to Mike who said that's not my store I need to reach out to his brother who runs that store. He said he forwarded the email to his brother. I never heard from anyone at that store. I feel if the owner has been sent the email he should reach out to me the customer. I'm very disappointed in their lack of interest towards showing care or concern about the need of their customers. I refer people to Windy city pizza all the time, but they showed no concern at all about my situation. I have an issue with merchants who don't care if the customer is happy. If you look at the picture you will see no sausage. Normally the meat is plentiful. The picture is the sausage pizza. The sausage was very skimpy to none.
TERRY TIBBSGriffin

TERRY TIBBSGriffin

hotel
Find your stay

The Coolest Hotels You Haven't Heard Of (Yet)

Find a cozy hotel nearby and make it a full experience.

hotel
Find your stay

Trending Stays Worth the Hype in Chesapeake

Find a cozy hotel nearby and make it a full experience.

Wanted to see if I could get a REAL CHICAGO STYLE PIZZA, in the 757. And I think I found it! We got to the restaurant within an hour after they opened on a Saturday, and it was not busy at all! We were sat immediately and decided to out in an order for an appetizer. We chose the buffalo chicken dip. The dip was served with pita bread and they were the perfect texture. If you’re like me and don’t like your bread burnt or super crisp, then you would like the pita bread. Fluffy. The dip was amazing and the perfect amount of buffalo! Wasn’t too heavy either. The dip was 8.95. Now onto the pizza: it was a deep dish, Chicago style pizza. We added sausage as a topping, and it was so good! I honestly couldn’t speak highly enough of this pizza. It was so good! It was 22.99 before the topping, which was an extra 1.75. The price is up there for a pizza, but honestly it was worth it because the pizza is so filling, it would comfortably feed 3-4 people. My husband and I ended up taking some to our friends who couldn’t make it, cause we couldn’t finish it at the restaurant. If you’re trying to find a good pizza place to eat with some friends, this is it! Service was fast and our waitress was very friendly! Cash and card is accepted!
Myan Kennon

Myan Kennon

See more posts
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Reviews of Windy city pizza chesapeake

4.3
(513)
avatar
1.0
16w

I've purchased a pizza from Windy City 2 times before today, put it in my back seat, drove home and had no issues. I just purchased a deep dish pizza, placed it in my back seat, drove home and opened the box to a soggy mess. I called the restaurant explained the situation and was asked if I wanted to speak to a manager (Callie? Kelly?), she explained that it probably shifted during transport, which I told her made sense. I picked up the pizza right as it came out the oven, so it hadn't set yet. She said the pizzas can be fragile (due to the sauce on top). My issue is how rude and dry she was about the situation- Kallie's response being "ok... what do you want me to do about it?" I told her being given a warning before leaving the store, whether it was verbal or a warning on the box, to place the pizza on the FLOOR instead of my back seat would have been nice. I thanked her for providing clarity and suggested that I come back to the store with the pizza and have it re-made or be given a refund. Kayley says "no. I'm not doing that", leaving me to realize that the "what do you want me to do about it?" question was rhetorical, and instead, a way to add some humor to what I'm sure is a very exciting life of serving pizzas. I called back up to the store to ask for her name so I could write this review and the owner, John, came to the phone and explained that Kally is his wife and asked why she needed to tell me to travel with the pizza laying flat (cue laughter in the background). He hung up as I started telling him how surprised I am at how rude they were being. John is running what seems to be a relatively successful business, which takes a brain to do, so I doubt he actually thinks I drove with my pizza in hand or anywhere other that what I originally said- in my empty back seat. My experience before today has always been pleasant, because I've only ever dealt with the young woman on the register, which is why I was shocked to know that the people who actually run the place don't care how they speak to the people...

   Read more
avatar
2.0
4y

I visited this location on Sunday August 22nd. First of all I now live in VA. but I grew up in Chicago. I discovered Windy City when it was fairly new. I was so excited to have some Chicago real deep dish pizza. I usually drive to the VA. Beach location, which is an hour or more. I decided this particular day I would try the Chesapeake store, a little less driving. ALWAYS stick to what you know so there will be no disappointment. I have been to the VA Beach location on several occasions. The problem was I ordered 2 pizza's drove almost an hour to get the pizza. Chicago deep dish pizza has sauce on top, sausage or whatever the meat is all across the pizza not skimpy, then the cheese. One pizza had sausage and the other had half cheese and half pepperoni. I have included a picture of what was left of the pizza. We literally had to look for the sausage. I called the VA Beach store on Monday to express my disappointment. The manager on duty was Tasha. She ask me to email her a picture since I still had some leftover. She said she would get back to me after she had a chance to look at the email. I waited 2 days she never responded. I called again by the third day because no one reached out. I spoke to Mike who said that's not my store I need to reach out to his brother who runs that store. He said he forwarded the email to his brother. I never heard from anyone at that store. I feel if the owner has been sent the email he should reach out to me the customer. I'm very disappointed in their lack of interest towards showing care or concern about the need of their customers. I refer people to Windy city pizza all the time, but they showed no concern at all about my situation. I have an issue with merchants who don't care if the customer is happy. If you look at the picture you will see no sausage. Normally the meat is plentiful. The picture is the sausage pizza. The sausage was very...

   Read more
avatar
1.0
3y

This place is trash !! They don’t do refunds but serve you burnt nasty food. Went here because I’m from Chicago so I know real Chicago style pizza this ain’t it !! Pizza taste like it was frozen pizza you buy at a grocery store. Keep in mind this place is a franchise & the owner has a NO REFUND policy. I retuned my food untouched uneaten I ordered a medium Chicago style thin crust and a sampler came close to $40. When I opened the sampler it was obvious it was cooked in old dirty grease it was burnt black the wings looked disgusting the pizza looked ok so we kept that. I politely asked the owner white female with glasses I don’t know her name but I asked her if I could please be refunded for the sampler due to it being burnt. She rolled her eyes at me and said no you can’t just order food and get your money back cause you don’t like it. I couldn’t believe the way she was talking to me rude didn’t offer a remake or refund. I said well we don’t want it she then took it and gave the food to the employees in the back. I can’t make this stuff up. I called the police but they said it was a civil matter I throw the pizza away so I’m out of almost $40 because the owner is trash !! She’s claiming not to be a racist because she has a black husband or boyfriend she was so unprofessional and I think if I was a white female I would’ve gotten better treatment. I contacted the Virginia Beach location and asked them their policy they stated there’s been several complaints about the Chesapeake location and they do things differently over there. So I’m guessing I’m not the first to complain. If you decide to go here hopefully you like the food cause if not there’s a NO REFUND or remake policy if they feel the food looks fine it’s up to their discretion. Wish we would’ve...

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