Craving real Chicago deep dish but stuck in Florida?
Hillary’s Chicago Pizza in St. Augustine proves the pie absolutely travels, bringing flaky crust, tangy sauce, and gooey cheese to the Sunshine State with heart and old school craft.
Tucked along US 1, this cozy, family run spot is where patience meets pay off.
Pull up a stool, sip a craft beer, and let that hour long bake transform your night.
The Chicago Pie That Started It All
You hear it before you see it, that soft hiss when the server sets down the Chicago pie. The rim is tall and burnished, a golden wall holding back molten mozzarella and a bright, tangy tomato sauce with a whisper of wine.
One slice in and you understand why an hour wait is part of the ritual.
The crust here bakes up flaky yet sturdy, a tender bite that carries sausage, pepperoni, or spinach without sagging. Sauce leans savory over sweet, layered with herbs so you taste tomatoes first.
Cheese stretches in long ribbons, the kind you twirl and laugh about because it refuses to let go.
What makes it special is intention. You can tell the dough was rested, the sauce simmered, the bake monitored, not rushed.
This is Chicago spirit translated for coastal Florida, proof that technique travels when you care enough to pack it properly. Bring friends, share the first slice, and save the corner piece for yourself.
Thin Crust Tavern Style Triumph
If you lean thin, Hillary’s still has your back with classic tavern style. The dough is rolled whisper thin, baked to a delicate crisp, then cut into squares that invite grazing.
Every bite snaps, a clean crackle carrying balanced cheese and zesty sauce.
There’s a satisfying contrast between edge and center, with corners that crunch and middle pieces that feel almost cracker light. Toppings stay modest so the bake shines.
You taste oregano, a faint garlic hum, and that signature tomato twang that keeps you reaching.
Order a pint and settle in, because this is social pizza, built for conversation and stories. It eats fast but lingers, the kind of pie you promise to have just one more square of.
Chicago roots, Florida ease, perfectly at home beside a cold beer and a friendly bar staff.
Meatballs Worth the Wait
Before the big pie arrives, meatballs. They come nestled in a bubbling red sauce, spoon tender but still structured, with a nutty Parmesan snow drifting on top.
One forkful and you taste the old school confidence that runs through this kitchen.
They are seasoned assertively, kissed with garlic, herbs, and a little pepper warmth. The sauce clings, bright and savory, perfect for dragging bread through every last streak.
It is a smart move to order these while the deep dish bakes to glory.
Share them, trade stories, and reset expectations for what a simple appetizer can do. When a place nails meatballs, it usually nails everything else.
Here, they set the tone for a meal made with care, reminding you patience and comfort belong together.
Cheesecake to Close the Show
After deep dish, dessert needs presence, and the cheesecake delivers. It is dense yet silky, balanced sweetness with a clean finish that keeps you from tapping out.
A ripple of strawberry on top adds brightness without overwhelming the cream.
The crust crunches softly, buttery and confident beneath the smooth filling. This slice feels celebratory, the kind you tuck into a to go box and then eat in the car anyway.
It is comfort in a tidy triangle, right when you think you cannot manage one more bite.
Pair it with coffee or a final sip of red, then call the night a win. You came for pizza, stayed for hospitality, and left with cheesecake memories.
That is how a small spot turns into your go to place faster than you expected.
Craft Beer, Easy Vibes
Hillary’s feels like a locals bar that happens to serve Chicago greatness. The craft beer lineup rotates with thoughtful picks that cut through rich cheese and sauce.
Grab something crisp while the deep dish bakes, and the wait becomes part of the fun.
There is no rush, just good conversation and classic tunes. Staff remembers faces and gives straight advice on sizes, slices, and timing.
You feel looked after, which is why a pint often turns into two and pizza turns into plans.
The pairing possibilities are easy to love. Lagers for Italian beef heat, malty ambers for sausage, citrusy pale ales for mushroom pies.
It is a bar program with purpose, tuned to the food and the neighborhood, never fussy.
How To Time Your Deep Dish
Plan your deep dish like a pro. Expect 45 to 60 minutes from order to slice, and treat that window as your appetizer hour.
Start with meatballs or cheesy garlic bread, grab a beer, and relax into the rhythm of a proper bake.
The result is worth it, because a rushed deep dish is never the one you remember fondly. Crust needs time to set, cheese needs time to melt into strata, and sauce needs time to concentrate.
When it lands, the table goes quiet for a reason.
If you are in a hurry, ask about slices or go thin crust. Otherwise, lean into the ceremony and let anticipation season the meal.
You came for Chicago patience and flavor, and Hillary’s serves both generously.
Small Space, Big Heart
It is a small room, which is part of the charm. You can see the bar, hear the kitchen rhythm, and watch locals trade stories with the owners.
That closeness turns dinner into a neighborhood moment rather than a transaction.
You will likely meet someone who swears by their favorite order, and you might leave with one of your own. Staff keeps things moving with candid advice and a trooper’s attitude on busy nights.
The friendliness feels earned, not scripted.
Come as you are, grab a table or a stool, and settle into the glow. This is where Chicago know how meets St. Augustine hospitality, no fuss needed.
The space may be small, but the welcome is big enough to bring you back.
Service With Chicago Soul
From the greeting at the door to the check in during the bake, service carries Chicago soul. You get straight talk about sizes, honest timing, and real menu guidance.
That authenticity builds trust fast and makes first timers feel like regulars.
Owners are present, engaged, and proud of the craft, and the team mirrors that energy. When it is busy, the bar still hums with patience and humor.
You notice the small touches, like water refills and fresh plates for a messy slice.
It is refreshing to be treated like a neighbor instead of a number. You leave with a handshake energy that lingers long after the last bite.
That is the kind of hospitality that turns a pizza joint into a destination.
Plan Your Visit
Hillary’s Chicago Pizza sits at 1974 US 1 in St. Augustine, an easy pull in off the highway. Hours lean afternoon to evening, with Wednesday through Saturday running 12 to 9 PM and Sunday until 7 PM.
Mondays and Tuesdays are closed, so plan accordingly.
Call ahead at +1 904 209 5960 if you want to check on slices or wait times. The website posts updates and specials, and the bar holds a smart rotation of crafts and wine.
It is a cozy room, so earlier arrivals help, especially on weekends.
Whether you are a local or passing through, map it once and save the pin. This is a repeat stop kind of place, where a perfect corner slice fixes a long day.
Come hungry, bring patience, and leave with leftovers and a smile.