Celebrate Deep Dish Pizza With the Best in Florida—A Must-Try Hotspot for Pizza Lovers

Anyone who knows me knows of my deep-rooted obsession with pizza. I cannot get enough. I'm the type of person who enjoys piping hot slices for Friday night dinner, then wakes up and indulges in cold pizza for breakfast Saturday morning. This culinary obsession has turned into more than just ordering from my local spot, but a quest to find some of the best pizza in the country, one trip at a time.

I stumbled upon a bit of a gem in St. Augustine, Florida, after a recent trip up the east coast. And while deep dish pizza was never my forte (I prefer a solid New York slice), Hillary's Chicago Pizza in St. Augustine quickly changed my mind. Could this be the best deep-dish pizza in Florida? Let's find out.

If you've visited Chicago or have any knowledge of their pizza preferences, then you are aware that the sauce-forward, built upside-down, deep-dish pizza that hails from this city cannot be challenged. Unless, of course, you're from Detroit, but that's a rivalry for another time. The world-famous Chicago deep dish is a culinary icon in its own right. This hearty, cheese-loaded creation was first crafted in 1943 by a local pizza chef, and it’s been making headlines ever since. What sets Chicago deep dish apart is its buttery, thick crust that’s more like a pie than a traditional pizza. It’s layered in reverse—cheese goes down first, then toppings, and finally, a robust tomato sauce is poured on top. Some argue that it’s not just pizza—it’s a whole experience.

Here's the thing - not everyone is going to be traveling to the Midwest to snag a slice of pizza, which is why we're ever-grateful that places like Hillary's Chicago Pizza exist, bringing this culinary icon to us here in Florida. Co-owned by Hillary and Bruce Lake, both native Chicagoans, the restaurant specializes in traditional Chicago-style deep-dish and thin-crust "Tavern Style" pizzas. Their deep-dish pies are particularly noteworthy, featuring a rich, buttery crust and generous layers of cheese, meats, and vegetables.

Understanding that quality takes time, especially when crafting deep-dish pizzas from scratch, patrons should anticipate a cooking time of at least 45 minutes for a full pie, with waits extending during peak hours. To minimize wait times, especially on busy weekends, it's advisable to call ahead and place an order. Or sit, grab a craft brew, and get to know the locals.

Beyond pizzas, the menu offers a variety of specialty sandwiches, fresh salads, and delectable desserts. To complement your meal, Hillary's boasts an impressive selection of 24 craft beers on tap, focusing on artisanal brews from Florida and Illinois, as well as a curated wine list.

So, next time hunger hits, and you want to sink your teeth into a deep-dish pie, head on over to Hillary's Chicago Pizza in St. Augustine. It's a taste of Chicago in the heart of Florida's oldest city.

Want to try more family-friendly experiences in the Sunshine State? Check out the great activities and tours available through Viator!