We've literally just left from this place. I had to leave a review which I never do. This place is great! The owner is so friendly! We ordered the deep dish pizza and it was amazing! Our kids had a small thin crust pepperoni pizza and they ate the entire thing, which they've never done before. The place was clean, good music, great family games. We will certainly be going back to try more items off of the menu. read more

This time no mix-up on the deep dish toppings and it was very good! I'm usually not the biggest fan of deep dish, but they really do a good job from the tomato sauce to the toppings (sausage and pepperoni) this time around. Everything fresh and good amount too! Everything was promised to be ready when asked for! read more

Windy City Pizza - Sausage Deep Dish Pizza - Pizza Near Me - Chesapeake, Virginia

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That deep dish pizza is legit and represents Chicago with pride. I am so happy not to have to buy frozen pies and have them shipped, because I now have the real deal in my own back yard. Stands tall with the best of them! read more

This was our first experience at a Windy City Pizza. This was at their Chesapeake, VA location off Kempsville Rd. We were greeted and immediately seated. The atmosphere is cozy and reminiscent of pizzerias of New York. We started with the Mozzarella Planks. They arrived at our table hot a fresh. The marinara was sweet and had great flavor. The cheese pull was amazing. We ordered a medium deep dish pizza with pepperoni. Flavors were spot on. The waitress was extremely professional and made routine stops to inquire if we wanted drink refills. Chesapeake is not known for their pizza and Windy City Pizza is changing that, one pie at a time. We are definitely coming back to this location in the future. read more

Windy City Pizza - Windy City Deep Dish - Pizza Near Me - Chesapeake, Virginia

We catered from Windy City for our rehearsal dinner and it was delicious! Our guests (some from Chicago) were well pleased. The large greek salad was great, in my opinion. 3 deep dish pizzas fed many. We also had the beef sandwich set up. Highly recommend and am glad to have such a place in the Tidewater area. read more

So I was craving Chicago style deep dish pizza, and looking at one of my regular places, suddenly realized in a panic that my regular pizza place had closed! A quick search on yelp revealed that Windy City Pizza had good reviews so I stopped by to check it out. I got the southside pizza and it was very good with a nice blend of sauce, cheese and toppings inside. If you are looking for a whole meal of a pizza in a single slice, look no further - highly recommend! I recommend calling ahead because Chicago style pizza takes 40 minutes to make. I called it in to the Chesapeake location, and it was ready for pick up. If you do happen to eat inside, there's a lot of Chicago memorabilia decoration and I heard the owner is originally from Chicago so that's pretty cool. read more

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Was craving pizza so I had to come get their delicious thin crust. My church family introduced me to Windy City and I introduced my husband to it. I had to create my own pizza due to the fact my husband doesn't eat pork. The medium was a good size & had plenty of leftovers. I got olives, mushrooms & banana peppers with pepperoni & bacon on one side and beef on the other.The pizza was fresh & tasty. My husband enjoyed it too. Definitely will be coming back for pizza night. read more

Windy City Pizza - Medium Pizza half beef other half pepperoni and bacon with mushrooms, olives & banana peppers - Pizza Near Me - Chesapeake, Virginia

Classic tasting pizza. Thin, crispy, staying true to what a pizza should be. Cool atmosphere, awesome staff, and the rest of the menu looks awesome. read more

Windy City Pizza - Chicago tavern style pizza - Pizza Near Me - Chesapeake, Virginia

A little pricey, but, worth it. My small pizza was $34, but, I ate off of it for 2 days... delicious! I will definitely return.

My husband and I ordered takeout on a Thursday evening. He had just came back from a work trip in Chicago and really wanted Chicago style food so we were happy to have this so close by. Reviews online were very positive so we were optimistic. Hot dogs were okay, nothing special, but I do appreciate that they really do them Chicago style! The pizza was a bit disappointing. The cheese wasn't fully melted and we felt like they needed more sauce on top. I feel as though we may have just ordered on an "off" night since other reviews were so positive, so we may need to try again and get a thin crust pizza to try something different. read more

Windy City Pizza - Chicago style deep dish pizza and dogs - Pizza Near Me - Chesapeake, Virginia

Chicago style pizza.. we were excited about this but it didn't live up to it! We ordered the Deep Dish pizza (it takes 45 minutes to cook). While waiting we ordered a sampler platter (cheese planks, corn fritters and hot wings). They were mediocre, at best. Everything was like something you get in the frozen section of a grocery store. The pizza.. it was just OK. The sauce didn't taste like much, it needed something more to give it flavor. The toppings weren't anything special. The crust was pretty good. The place is decorated in all types of memorabilia representing Chicago. There was only 1 server taking care of everybody. read more

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We've been coming here for years, and somehow I've never reviewed it. This could be for the best though, as my early reviews lacked substantive detail or information. You come here for the pizza. That deep dish Chicago style pizza. The other pizzas do look good, and even tonight I heard some patrons commenting that their pizza was better than another local place that is known for great pizza. That being said, I've never ordered anything other than the deep dish. I've never been to Chicago, but from everything I've read, this pizza is the closest you'll come to true "Chicago" pizza outside of the Windy City. The other food is good, wings, gyros, etc. and I've sampled some of that, but I keep coming back for the pizza. It has a 45 minute cook time, so there's been a time or two I've called ahead to order it so we wouldn't be waiting. The walls are covered with all things Chicago. Bears, Cubs, Bulls, and Blackhawks are well repped. Pics of the skyline, local Chicago products help to make you feel like you're in a pizza place in the upper Midwest. The service is good, just keep in mind that it's a small family run joint. You may wait a beat or two, but they always give great and friendly service. read more

Windy City Pizza - Thai sweet wings - Pizza Near Me - Chesapeake, Virginia

Omg the food was amazing! They have a buffalo chicken dip with pita bread that taste better than getting wings. Was my first time eating and I would go back for that alone! I also had a deep dish pizza and my one complaint is I ordered it with steak and pepperoni, but the steak seemed almost non existent. Other than that, the food was really good! read more

We've been dying to try Windy City, mostly because it seems to be the only place in the 757 that has deep-dish pizza which just happens to be my husbands one true love. We made it to the Chesapeake location this past weekend with a group of friends and ordered a wide variety of their menu. First things first, ambiance and service are lacking. There seemed to be just one server on a Saturday night for the whole restaurant, which meant that we saw her at the beginning when we ordered and when she delivered our checks. Luckily, another employee from the host stand stepped in when she saw that the server was swamped. Our server definitely was trying, but there were many awkward conversations, specifically when the server complained to us about previous tips from other tables. Unprofessional and weird. Another issue was that the specials board was apparently irrelevant. We tried ordering the specials listed and the server stated "oh those aren't the specials anymore. They've been up there forever". Unprofessional and misleading, which is easily fixable. It just seemed as though no one is currently caring for the place. In addition to these few things, they still have Christmas decorations up and they have tables covered in crayons and coloring books, which just looked messy. Their music machine is apparently also broken, so the whole restaurant felt eerily silent with no music. Food-wise, it kept my review above a one-star. Because the deep-dish pizza was pretty good, we would come back but only for the pizza and only for takeout. The fries and the fried pickles were served lukewarm and mushy. The wings were pretty good and so were the mozzarella planks. Overall, like stated above.... I recommend sticking with the pizza and doing takeout because the dine-in experience was severely lacking. read more

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What a pizza, great flavor and piping hot! I had the Pulaski and cant wait to try the Deep dishes. Thank You​

Have ordered here a couple of times, usually for pickup to eat at home. The pizza is the best deep dish you can get around here. Staff is always pleasant, no complaints there. I would check the pizza before you leave though, last time I got a deep dish (during the bears-Rams playoff game) they forgot to cut the dang thing. Didn't see it till I got home. Not really tailored for dining in - dining area is a little shabby. Their Chicago dog is also delicious. read more

Make sure you have time. I knew it would be longer ordering the deep dish but they didn't say how long. It was just over an hour from the time we ordered to the time it got to our table. We ordered the heart attack and it was excellent. We also got the Italian sandwich with fries. I definitely wouldn't do the fries again. They tasted like they hadn't been cooked all the way. Although the sauce for the sandwich was nice and hot, the meat was not. read more

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My opinion has changed about Windy City Pizza, let's get into it... Admittedly, I'm generally not a fan of Chicago Deep Dish style pizza. That said, we recently had some friends over to our home for a get together and my Wife ordered pizza from Windy City. It was really good. The crust was beautifully cooked to a crispy golden brown. It was light and airy and everything tasted great. In retrospect, my first review was shortly after they opened their doors, so I'm willing to admit that it was unfair to be so harshly critical, for that I apologize. read more

Ordered a Chicago beef sandwich with fries. The fries are solid. The beef sandwich my husband liked and he would order it again. I like mine like Portillos-juicy and sloppy with all smoke (peppers and toppings on top). The sandwich was good just dry-for me. For my husband it was fine. read more

Food was really good, and as for portioning, it is great on that! The salad was super big, came with a good amount of dressing as well. Their ranch is nicely homemade, and their balsamic is also nicely blended. The pizza was really nice, the marinara was flavorful, the jalapeños were spicy enough, and you could actually pick up a slice if you wanted to. I'd go back if it weren't so far. read more

Windy City Pizza - 12" Deep Dish, half cheese, half jalapeño, onions, and salami - Pizza Near Me - Chesapeake, Virginia

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If you call this place for orders, always say hold on a second, after 6 minutes still waiting. I called again I told I was on hold 6 minutes. Can't you take 30 seconds to take an order? Then hanged up. Never never order this place... read more

We love Chicago style. A little disappointed in the pizza tonight but the flavor was good. My brother and sister in law come in all the time. They love this place. Apparently when the owner isn't here the kitchen staff goes wild and doesn't pay attention. Incorrect food orders. Substandard pizza. I'm leaving 4 stars because they are typically great. Just a bad night. While the cats away... read more

Windy City Pizza - Deflated Chicago style pizza. Not a typical experience. - Pizza Near Me - Chesapeake, Virginia

The first time in my life I've tried deep dish pizza, I'm glad I came here! We came at a time when it wasn't busy and got our food under the 45-minute mark. Also, we mentioned places in Chicago, and our waiter started naming names. The pizza was yummy yummy! Please try this place out! It is as authentic as you're going to get to true deep dish pizza! read more

Windy City Pizza - Southside Special - Pizza Near Me - Chesapeake, Virginia

This was my first time at the Chesapeake location. As someone who lives in west burbs of Chicago for 20 years, I think I know a few things about Windy City cuisine. I walked in and the host was on the phone taking an order, it took him about 3-4 minutes to realize that I was there. I felt like heel Roman Reigns, I just wanted to say to him, "Acknowledge me!" Anyway, I got sat and I had a very friendly and personable female server, she had a great attitude and approach. I ordered the Italian beef with cheddar, sweet peppers, and hot peppers with a side of fries. Very flavorful juicy beef, although I wanted to taste the Italian seasonings a little more. The hot peppers had that nice kick of heat and flavor. One thing that was different from what I'm used to is the sandwich was put under the salamander to melt the cheese. I like toasted rolls, but when you have so much gravy and juice it can just break the roll down. It was one of the better beef sandwiches I've had, and until Portillos come to Virginia, this is a fine place to go. read more

Windy City Pizza - Cheesy beef with fries. Cheddar Mozzarella - Pizza Near Me - Chesapeake, Virginia

Quick service I ordered a Cheese pizza. Pizza was hot and tasty for a late night snack c read more

the service was great from everyone except the owner. I came there afterwork for take out. got my daughter pizza and myself mild wings. when I got home my wings were not cooked. when I called the restaurant the lady kindly asked me to send her a picture which I did. she responded the next day and apologized for the late response and said she talked with the owner. I called the restaurant when I got off and spoke with Kelly (the owner) who proceeded to tell me that the wings were not uncooked and that the picture that she saw was actually bone marrow. I'm very unsatisfied with the way this situation was handled and even though the pizza was very good I will be spending my money elsewhere for now on. read more

WINDY CITY PIZZA is HORRIBLE their customer service is in the TOILET!!!!! As a company, we order from them all the time and they show no respect. The manager needs training even though this is a family business they are disgusting. I have attached a picture, the young lady said people order pizzas like this all the time..... GTFOH When my boos re-ordered they made him WAIT an additional 30 minutes because they are horrible rude people in that establishment! How embarrassing I wish I could give them a NEGATIVE 10 stars! 5 for the MANAGER and 5 for this hard crust! Just TRIFLING! read more

Windy City Pizza - This was supposed to be a thin crust cheese pepperoni - Pizza Near Me - Chesapeake, Virginia

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This is what a $20 1/2 cheese & 1/2 pepperoni looks like from Windy City Pizza Chesapeake, straight garbage. Would have done better getting a $10 frozen pizza. read more

Windy City Pizza - Pizza Near Me - Chesapeake, Virginia

The food is not good, it's definitely not Chicago tasting either. Don't be fool by the name Chicago. It's no where near. Customer service ridiculous. You ask for your food a certain way, they make as they see fit. Do Not order the Gyro sandwich read more

Windy City Pizza - Pizza Near Me - Chesapeake, Virginia

Have since been back a few times. Have learned a bunch about this place. One, it is worth that wait! They even advise now of the time it takes to bake a deep dish. Two, the service is always accommodating and on point. They are great at taking care of you. Three, this is a place that specializes in deep dish. So if you don't order deep dish, this may not be the place for you. Even though the other menu items are ok the deep dish is the reason we go. It has to delivered every time for us and this has become a pretty regular spot for us. So I am updating my initial review to reflect what we have learned. Enjoy! read more

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. We started with a Greek salad, and it was fantastic. The dressing was great as well. We couldn't decide between the Windy City Special and the Heart Attack, so the waitress recommended d we do half in half. PERFECT!!!! Excellent food, great service, and definitely worth the visit. read more

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I'm new to the area, born in IL and this is by far an exact of Giordano's in Chicago. Nothing else is even close to Windy City. Not only is the food outstanding but the owners are very friendly and you feel like family when you walk in the door. They also have games for adults/kids to pass the time as you wait for your true Chicago style pizza pie! We will definitely be back! read more

Ordered the 14-inch sausage and onions last night for dinner. The pizza was literally tasteless. It's as though they forgot to season the pizza. The only saving grace was the pizza was ready when I went to pick it up. read more

I only tried the cheese pizza on a thin crust. I can't believe I'm saying this, but it had way too much cheese. The thin crust was cooked perfectly but it was too much cheese. It was like chewing cheese bubble gum. If they would have gone light on the cheese, this pizza would've been amazing. I don't know if I would go back. read more

My husband and I have both called Chicago home at some point, and while deep dish isn't something we ate often while living there, it's so nice to have an authentic taste of Chicago here in Hampton Roads. On our most recent visit we did the Windy City Special- the crust is brushed with garlic & oil, and toppings include Italian sausage an baby spinach. The sausage is my favorite thing about Chicago deep dish, large flavorful chunks adorning the thick bed of cheese and covered in sauce, and theirs is authentic in every way. The ovens even come from Chicago! The spinach was just enough to make you feel like you are eating SOMETHING healthy amidst the heavenly solid inch of cheese. Windy City is run by two brothers from Chicago, and the wife of the Chesapeake shop's owner was our server. She was incredibly nice! We have never experienced anything less than wonderful service with Windy City. We're looking forward to coming back to try some of their other Chicago favorites. read more

Windy City Pizza - The Windy City Special- garlic and oil topped crust with Italian sausage and spinach. - Pizza Near Me - Chesapeake, Virginia

This is the most authentic Chicago style deep dish I've had outside of Chicago. The box weighed like 10 lbs! The sausage and pepperoni were fresh and the mozzarella was good and plentiful! Was absolutely amazing! read more

Windy City Pizza - 12" Medium Pizza "The Cicero" - Pizza Near Me - Chesapeake, Virginia

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My son and I came in on Friday afternoon about 2 o'clock & sat in the dining area. The dining room is open on Friday and Saturday otherwise it's takeout only. I enjoyed a couple IPA beers, sausage bites, and Gyro with fries. The sausage bites were a surprise to me because of how juicy and flavorful they were. My son rated the fries a nine out of 10 and later change his mind and said they were a 10 perfect! The gyro meat and sauce was as it should be and tasted like it was right from Chicago. The pita bread could have been placed on the grill for another minute. I ordered a deep dish sausage pizza to go which I won't rate because it was cold when I ate it later that night. However it was fantastic even cold. Round trip was about 60 miles which I would happily do again, I strongly recommend Windy City Pizza. Cheers! read more

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At first, I was not sure what to expect but when I opened the box and I saw that oooey gooey goodness oozing underneath all that marinara, my mouth began to water and I knew that I was in for a treat! I ordered a half pepperoni for pops and a half spinach and pineapple for myself. Spinach and pineapples she says? Don't knock it until you try it! Perfect hint of sweet to accompany the bitterness of spinach, tang of sauce and plethora of savory cheese. Overall, really great pizza for Chicago style deep dish not located in Chicago. Definitely a hidden gem in the VA. read more

Windy City Pizza - Deep dish - half pepperoni, half pineapple, spinach and mushrooms all over - Pizza Near Me - Chesapeake, Virginia

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For those who are gluten sensitive, their gluten free pizza is the best in the area. So, so good. (Just a note: I do not have celiac so I do not know about their cross contamination.) I'm always looking for people to review GF items so I hope this helps someone too! read more

Don't let the Karen's complaining fool you: no one knows Chicago food better than a Chicagoan. This place is home; great beef, great dogs, great pizza. I would give it 6 if I could. P.S. make Maxwell St. Polish! read more

Windy City Pizza - Italian Beef, Hot Dog, Pizza Puff. - Pizza Near Me - Chesapeake, Virginia