Some restaurant stories are about the food. Others are about mystique and buzz that circulates long before you eat there yourself. Many are about the ambience and service. Hillary's Chicago Pizza is about the owners, Hillary Lake and Bruce Longanecker Jr., who have created their tiny restaurant out of passion for community and a lifetime of love for their city — Chicago!
The story unfolds its layers of history that began with The Sedgwick Stop, their first neighborhood tavern and eatery along Chicago's train line at one of the stops on Sedgwick Avenue. What a great name for Bruce and Hillary’s successful “Cheers-style gathering place” that was not only easy to locate but known for serving the best burger in town and best chicken sandwich in their gastro pub. Articles about them all agreed that their mission was “to make everyone feel at home.”
The neighborhood pub “where everyone knows your name” couldn't have been better suited to anyone other than Bruce and Hillary. Years later, their St. Augustine eatery now exudes the same heartfelt familiarity at Hillary’s Chicago Pizza, which seats 30 guests on any happy night at the bar or handful of tables.
Located at the crossroads of U.S. 1 and State Road 312 in St. Augustine, there is numerology happening here that couldn't be a better karma for Hillary: 312 is also the Chicago area code and their official address is 1974 (Hillary’s birth year)! This couple’s destiny was planned long before they landed in Northeast Florida.
Bruce and Hillary came to Florida for family connections, although they had no ultimate plan about their culinary future. What they did know was that they couldn’t find their favorite Chicago-style pizza anywhere.
Bruce was, at the time, commuting from Jacksonville to Chicago and always bringing a warm deep-dish pizza (in the overhead compartment) to his darling wife. The timing of the COVID pandemic prompted them to consider making these iconic pizzas themselves, becoming familiar faces at many farmers markets from Nocatee and Atlantic Beach to Fernandina Beach. Their fans counted the days until their return, and each weekend they “sold out.”
When they heard about a proper kitchen and small eatery in St. Augustine becoming available, the magic happened quickly. They purchased the space with a beer-and-wine license at a perfect crossroads for Hillary’s Chicago Pizza to call home. In a year, their reputation has grown in what they call their “launching pad” to excite pizza lovers and fans of food from the Midwest. And it offers “way more than pizza,” according to Bruce.
“It's our gathering spot,” said Hillary. “It's a happy neighborhood meeting place and especially a nightly reunion of new Midwest neighbors.”
With pride in their made-in-house scratch kitchen that somehow produces an overwhelming number of the most scrumptious Chicago deep-dish and thin-crust pizzas, their little Mecca is a magnet for pizza lovers who just can’t get enough of their distinctive flavors and top-drawer ingredients. With fans who are either dining in or taking out — or are counting the days until Bruce arrives with whole pizzas at the farmers markets — Hillary’s Chicago Pizza is gaining momentum.
The Tutorial: If you are the first timer, there are two types of pizza in Chicago.
The thin-and-crispy style that’s cut into squares and referred to as “tavern style” is often served complimentary in some Chicago taverns as a great way to get customers to buy more beer!
The deep-dish pizza, which was invented by a chef in a local Chicago pizzeria (around 1943 as the story goes), is more of a special occasion treat. The pizza is really deep, the cornmeal crust rolled out by hand with a lot of ingredients that takes at least 45 minutes to cook. In Chicago, the trick is to pre-order before you arrive. This is also suggested at Hillary’s. It’s worth the wait.
For the adventurous lover of “Crafts on Draft,” with 24 craft beers, ciders and prosecco on top, jump into a few favorites like Homemade Apple Pie Cider, Mad Manatee IPA, Peanut Butter Porter or Karate in the Garage IPA.
While waiting for your pizza, try a key lime Caesar salad, warm pretzel with beer cheese or an appetizer of goat cheese in marinara. You can always do what the locals do and take home your favorite pizzas. And for a crowd, their catering extends to delicious baked pastas from lasagna to spinach-and-ricotta stuffed shells, grazing boards, salads and creative Italian-inspired appetizers.
Shhh it's a Secret: If you care to enjoy a “mash up” of Chicago and St. Augustine, do not miss Hillary’s Hot Honey Thin Crust Pizza with pepperoni, goat cheese, mozzarella, provolone and finished with housemade datil honey. You will not want to share this, even with someone you adore!
Hillary’s Chicago Pizza is open daily (except Monday) from lunch through dinner. See the new menu at: HillarysChicagoPizza.com.
