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Hillary's Chicago Pizza

4.3 (100 reviews)
Open 12:00 pm - 9:00 PM

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HILLARY'S CHICAGO PIZZA ATMOSPHERE

What's the vibe?
Happy hour specials
Dogs allowed

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Recommended Reviews - Hillary's Chicago Pizza

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Ira B.

A number of people told me to visit Hillary's for some great pizza, and I have no doubt that they truly enjoy the unique flavor and texture of Chicago Pizza - it's not exactly my style, but Hillary's does do a nice job overall of providing a nice dining area, excellent Greek salad, and a quality of pizza that many others enjoy. I found the pizza better on the second day when I reheated it at home. I found the outside of the business not so enticing, being right next to a check cashing store. Once inside however, the Chicago themed artwork, lighting hanging from the rafters, and the bar area we're all quite attractive. Service was also good on the day of our visit, we were told that the standard thick crust Chicago style pizza generally takes between 45 minutes and an hour to prepare, in case you're expecting to enjoy in-restaurant dining. Pricing for a salad and a shared pizza with drinks, tip and tax average about $30 per person, a reasonable value. Overall, the quality of the product is excellent, it's just not necessarily my preferred style of pizza.

Crust was soggy.  And falling apart.   (DEFINITELY NOT A CHICAGO DEEP DISH PIZZA)

DO NOT GO TO THIS PLACE! I was deceived with the ratings on Google. Service was horrible! And the deep dish pizza was unfortunately.. the worst I have seen and tasted in many years. The lady that took our order at the bar... was uncomfortably loud. As in screaming the whole time. Not only me... but you can see the other clients uncomfortable as well. Also, she was coughing... all over the place while serving the food to clients! Agrrr . Just an all around negative experience!

Kelly T.

We had heard about this pizza place from some other friends and decided to give it a try today for lunch. They are known for their Chicago deep dish pizza. The menu also offers thin crust pizza as well as salads and sandwiches. They also have plenty of Chicago themed artwork and decor. We started with the Greek salad and it was really good with Romaine lettuce, tomatoes, cucumbers, onions, peppers, artichokes, olives and feta cheese. The dressing was also good. We decided to go with the Chicago thin crust pizza pie. It had sausage, mushrooms, green peppers and onions. It was tasty. Service was friendly and professional from our server, Linda.

Meat lovers slice
Bill C.

WOW!!! Welcome to CHICAGO... A True FIND. This is a family owned and operated business. The pizzas are made to the highest standards. A pizza lovers paradise. I had the meat lovers deep dish pizza. The meat was plentiful,sauce was excellent "Mom's perfected recipe ",just the right amount of cheese and the pizza crust was over the top. The friendly staff and local regulars make you instantly feel like you've walked into "Cheers" You MUST try the Italian Beef sandwich,best around and they import some of the best cheesecakes south of NYC... The deep dish takes 45 minutes so if that's what you're going for call in advance and they will have it ready .

MFW - Deep Dish Pizza: Personal Size
Delvin D.

We were so happy to find Chicago pizza and Italian beef on our trip to St. Augustine. This place absolutely deserves to have Chicago in the title of their restaurant. Everything was authentic Chicago! The owner, Bruce, knew we were from Chicago and wanted to make sure everything tasted delicious and just like home. We need you in The Villages! Thank you!

A Chicago Deep Dish in Saint Augustine.  Expect a 45-minute wait for it to cook properly.
Dave O.

Great food! Great seasonal beers! Great bartenders and employees! The best Chicago style pizza I've ever had. The best thin crust pizza I've had in Florida. I want to try some of their other food! The Chicago style pizza takes 45 minutes to cook so you may hay a few minutes to grab a cold one on a hot Florida day or evening. You really should. This way you can sample the beer specials at the bar. Some nights they also have wine sampling to try glasses or 1/2 bottles of wines. It's not just a pizza place but it can be because their pizza is fantastic. I'm a NJ/NY pizza guy with a Chicago pizza because of this place. Try it for more than a few reasons!

Roast beef and giardineira  pizza thin crust...
E M.

Ok folks yall know me when I say I think you should try a place then that's what I mean. Nestled in ST. AUGUSTINE FLORIDA, is a little restaurant called Hillary's Chicago Pizza. They have thin crust and chicago deep dish pizza (takes about 45 mins to bake) but worth it... sodas and beer and just good vibes. The food is great the service is mellow and they are a gem in a city that full of tourist and locals alike looking for something different... If you all know Chicago it's a city that revolves around good food, good conversations and friends and family.... Hillary's Chicago Pizza is the place for that. They also have homage chicago roast beef samiches (yes samiches) and ask about garlic dressing .... Just like I always say. Try it on for size. You can't miss. Yes I'm putting them on a high standard pedestal..... enjoy folks. You all can also check my reviews on instagram under: sailrbean It's review it anything and everything it's sailing .... Love peace yall...

Menu
Mike B.

Drove to St. Augustine and, as a Chicago native, had to visit Hillary's Chicago Pizza for some authentic thin-crust pizza. If you're a fellow Chicagoan craving a taste of home in the form of delicious thin-crust pizza with flavorful sausage and fennel seeds, reminiscent of your local tavern, then this is a must-visit. In addition to thin crust, they serve deep-dish pizza and Italian beef, accompanied by an impressive selection of craft beers. Definitely worth the detour to St. Augustine!

Italian Beef - Thin Crust Pizza

The thin crust Italian beef pizza was good. It was cooked well and had plenty of giardiniera. I prefer more beef and will order extra beef next time. Based on other reviews, my next trip will be for a combo. The owners are a very friendly couple who take pride in their menu. If you're missing your Chicago favorites, this is the place to find a few of them!

Laura P.

Came down for a yelp event and decided to eat here first. Super unassuming location but pizza really delivered. Ordered the monthly special brisket pie and the hot honey. Both delicious on the Chicago crust. Super crispy and tasty. They had Prosecco on tap which was so tasty. We also tried the dessert special cheesecakes made by a local chef. The chocolate covered key lime was legit. We will def be back. Love the place and the owners were so nice!!

Had to get a pie..  oh boy, they nailed the crust, tasted amazing.  It had a little kick to the sauce and gave it that chi town flavor.

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6 months ago

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Hillary L.

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7 months ago

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2 years ago

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1 year ago

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5 months ago

Our pizza and sandwich was amazing. Family friendly atmosphere serving wine and beer. TIP order ahead for your Chicago pizza.

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2 years ago

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Hillary L.

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8 months ago

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2 years ago

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3 years ago

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3 years ago

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3 years ago

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1 year ago

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2 years ago

Amazing Chicago style food!! Love the deep dish mushroom pizza!! My Mother loves the Italian beef dipped with hot peppers.

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Ask the Community - Hillary's Chicago Pizza

Any consideration to opening on Sundays once football season starts again? There are TONS of Bears fans that would love an authentic Chicago spot to eat, drink and watch The Beloved play.

ABSO-FREAKING-LUTELY! BEAR DOWN!

Beer prices? Can't eat pizza without beer :-)👍🍺🤪?

We have 24 rotating taps of craft beer, prices range from $4-$8.50

Do you have beer & wine?

Yes! 24 taps and a small wine list.

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Five Star Pizza

Five Star Pizza

4.1
(223 reviews)
1.1 mi
$

One of the few places in St Augustine open late for food other than Denny's or an Americana…read morerestaurant. I ordered the chicken bites and garlic knots. The knots were drowned in a flavourless oil with some garlic. I threw them out. They did however have good ranch and hot sauce for the chicken. I would give them a second chance w the pizza if I was in a pinch for a late night meal.

Shoutout to our local community heroes!!! We are so grateful for this venues fast delivery of…read morequality products!!! We needed this today! A busy weekend after weeks of holiday travel... thank you for this amazing save Five Star Pizza! We had a flyer in the mail for a free large pizza and the reviews have been fantastic. We opted for the family special once I created a pizza profile. A large 2-topping, garlic bread, and a 2-Liter soda!!! My husband made it home just in time to get the pizza hot and fresh!!! He made me look forward to my first bite as he enthusiastically said, "We can order from this place anytime! This is some of the best pizza that I've had in a while!". I definitely do agree!!! The cheese pull was perfect!! I loved the spice level in the pepperoni!!! And it was thin slices so they crisped up magnificently!!! The crust was the quality!!! Cooked well and the texture was wonderful!!! Not burnt or gooey... I am very picky. I was impressed! Their garlic bread (made daily) was generously swimming in their secret recipe garlic butter! Yummm! Then, the hot wings that we added to our dinner were cooked well-done as we ordered. Yay!!! This all washed down perfectly with our cold bottle of Pepsi!!! Yay!! And they added a sheet of coupons on our pizza box that lead us to a QR code that gave us yet ANOTHER coupon!!! Talk about a win win!!! As a veteran pizza maker (@2 years at Pizza Hut)... I am proud to support the masterpieces coming from this venue! And shoutout to exceptional speedy delivery time and the professionalism of the delivery person!!! He was very presentable and personable! God bless! 5 stars indeed!!!

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Five Star Pizza
Awesome cheese pull on my double pepperoni!!
Awesome cheese pull on my double pepperoni!!
Thin crust pizza

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Thin crust pizza

Hillary's Chicago Pizza - pizza - Updated July 2026

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