A Chicago Couple Opened A Deep Dish Spot In Florida And People Can’t Stop Talking About It

Some places serve pizza. Others serve a craving you did not even know you had until the smell pulls you in.

Somewhere in Florida, there is a spot where the air feels warmer near the door, the ovens glow like stage lights, and the scent of slow simmered sauce drifts out as if it knows exactly how to find you. You step inside curious, and within seconds you realize this is not just dinner.

This is an experience people talk about long after the last slice disappears.

Ever tasted a deep dish so rich it makes conversation stop? Wondered why strangers suddenly start comparing orders like they have known each other for years?

Or how one hidden pizza spot can quietly build a reputation strong enough to travel by word of mouth alone?

This is the kind of place locals hesitate to reveal and visitors never forget once they find it.

Exact Location And How To Find It

Finding Hillary’s Chicago Pizza is simple once you know the route. The restaurant sits just south of the historic district, close enough for an easy drive yet far enough to avoid heavy tourist gridlock.

If you pass local auto shops and small plazas, you are getting warm. Watch for the sign and the cozy storefront tucked into a compact retail strip.

The pin drops right where you need it, at 1974 US 1 in St. Augustine, with a straightforward pull-in off the main corridor and parking out front.

Arrival feels relaxed, like dropping by a neighbor who happens to have a serious oven. The entrance opens to a friendly greeting and the comforting aroma of tomato, cheese, and toasted dough.

Traffic on US 1 hums along outside while inside a pocket of Chicago warmth holds steady. Navigation is stress free, especially midday, and street visibility is good.

For pickup, slide into a spot near the door, run in, and you are back on the road with dinner under your arm.

First timers should note the posted hours: currently closed in the morning and opening at 12 PM on Thursday, with operating hours listed on the door and website. A quick call to +1 904-209-5960 confirms timing.

Backstory, Ownership, And Chicago Roots

Story matters here, and you feel it as soon as the owner greets you to walk through the menu. Hillary’s Chicago Pizza is run by true Chicago transplants who built the place around a shared affection for classic deep dish and tavern-style thin crust.

Reviews mention conversations with Hillary and Bruce, a duo often found on the floor explaining sauce choices, dough, and timing. That hospitality does not feel scripted.

It is the neighborly cadence of a mom and pop who remember what you ordered last time.

Public details about the full origin timeline are not exhaustively documented, so what you get instead is the living history on the walls and in the pie pans. Guests who lived in Chicago say the flavor transports them back.

Others try deep dish for the first time and grin like they have just learned a useful secret. The recipe stories revolve around patience, careful sourcing, and that signature tomato sauce, repeatedly praised for balance.

Ownership presence is palpable. Questions about crust, heat, or portion sizes often bring a quick, thoughtful answer.

There is pride in the process, but no rush. If you love hearing how something good gets made, linger near the counter and let the conversation find you.

Decor, Ambiance, And First Impressions

Inside, the space is intentionally intimate, the kind of room where a couple of tables turn into a friendly chorus during dinner rush. Expect compact seating, cheerful lighting, and the lived-in charm of a working pizzeria that prioritizes food and conversation.

There is an easy back-and-forth between counter and table, with staff sliding hot pies past a chalkboard or printed menu. It feels neighborhood grounded rather than polished showroom, which suits a place that pours its energy into the oven.

The vibe builds as pies come out and you hear the heel-tap of servers keeping pace. Guests chat about toppings and timing while the scent of roasted tomatoes hangs in the air.

It is small, so it fills quickly, and that closeness actually makes the experience more Chicago. The hum of US 1 fades to a background hush once the first slice lands.

Clean lines, sturdy tables, and practical touches frame the setting. Decor is not fussy, and the focus remains squarely on the plates.

The overall impression is warm and unpretentious, a room that invites return visits. Walk in with a plan, but leave room for dessert and a quick compliment to the kitchen on your way out.

Menu Overview And Notable Dishes

The menu at Hillary’s reads like a love letter to Chicago classics with a Florida-side smile. You will find deep dish as the headliner, tavern-style thin crust cut into squares, and the crowd-pleasing Italian beef, often praised for its faithful flavor.

Starters include meatballs, a pillowy pretzel with house cheese dip, and cheesy garlic bread on focaccia that regulars will nudge you to try. Slices of deep dish appear as a quicker option during lunch, easing the time crunch without sacrificing the experience.

Customization is encouraged. Build a pie with sausage sourced from Chicago, layer in peppers or spinach, and let the signature tomato sauce do its thing.

That sauce draws raves for depth and balance, leaning savory with a bright finish. The tavern pizza runs crackly and thin, perfect for sharing across the table.

Daily specials shift with the mood, often pairing a slice and a drink for value seekers. Portions are generous.

Expect leftovers from a family-sized deep dish unless your group is extra hungry or determined. The kitchen keeps it classic while avoiding gimmicks.

The story line is simple: a few things done really well, by people who care.

Signature Deep Dish: Taste, Texture, And Timing

Deep dish here respects tradition. Cheese goes in first, then toppings, then the bright red sauce blanketing the top like a quilt.

A proper bake takes patience, so plan for about 45 to 60 minutes on a fresh pie, depending on size and toppings. While you wait, enjoy an appetizer and relax.

The payoff is a pie that cuts clean, releases steam, and showcases that savory tomato pop. The crust is sturdy enough to hold the stack, with a gentle crunch on the edge and a tender interior.

Flavor-wise, expect a balanced tomato presence, not sugary, with a hint of herbal lift. Sausage is a standout, especially when sourced Chicago-style, offering fennel warmth without overpowering the cheese.

Portion sizes are generous; two to three slices will satisfy most appetites. Families often order large to guarantee leftovers, which reheat beautifully.

Servers will remind you to let the pizza rest so the molten center can settle. That little pause keeps the layers intact and avoids a cheese avalanche.

If time is tight, consider the deep dish slice option when available. Either way, the signature pie defines the experience, making good on the promise that drew you through the door.

Tavern-Style Thin Crust And Other Favorites

Not every craving calls for a fork and a skyscraper slice. The tavern-style thin crust at Hillary’s delivers a crisp, square-cut pie that eats fast and pairs well with conversation.

Expect a delicate crunch and a sauce-to-cheese ratio that keeps each bite light yet satisfying. Topping loads vary from classic pepperoni to veggie blends, while sausage remains a reliable favorite.

Because the crust is rolled thin, bakes run quicker than deep dish, making this a solid pick for weeknights or lunch.

Beyond pizza, the Italian beef earns applause for its Chicago faithfulness. Meatballs arrive tender with a savory sauce that has depth, and the pretzel with house cheese dip often steals the appetizer show.

Cheesy garlic bread on focaccia comes blanketed in mozzarella and begs to be swiped through that balanced red sauce.

For newcomers, a clever approach is thin crust for the table and deep dish as the main event. That pacing lets you taste the menu’s range while giving the big pie its needed time.

Leftovers hold up well, especially thin crust reheated to restore snap. Variety is the promise, and the kitchen keeps delivering.

Service Style, Pace, And Hospitality

Service at Hillary’s balances cheerful conversation with practical coaching about the bake. Staff greet at the door, walk newcomers through the timing, and help calibrate orders so nobody overcommits.

That includes honest estimates for deep dish, smart appetizer suggestions, and reminders to rest the pie before slicing. You will notice a steady presence from ownership, which sets the tone: friendly, attentive, and unpretentious.

Questions about ingredients or sourcing get real answers, not canned lines.

Because the room is small, pacing depends on order mix and peak hours. When a few tables go deep dish at once, service becomes a choreography of timers and trays, which the team manages with good humor.

Conversations often turn personal, like food memories from Chicago or first-timer curiosity about the sauce. The staff lean into those moments, which makes the meal feel more like a visit than a transaction.

Expect table checks that are timely without hovering. Refills and napkins appear right when you think to ask.

Pickup orders get the same attention, with clear handoffs and quick clarifications. In short, hospitality lives front and center, shaped by people who clearly love what the oven can do.

Pricing, Portions, And Value

Value here comes from generous portions and the kind of satisfaction that lingers into tomorrow’s lunch. Deep dish prices reflect the time, ingredients, and heft in the pan, with family sizes designed to feed a crew and still promise leftovers.

Thin crust offers a friendlier ticket while keeping flavor front and center. Daily slice combos create a quick-win option when you are watching the clock.

Appetizers are shareable and smart for bridging the deep dish bake.

While exact pricing can shift, the experience consistently feels fair for the quality. Reviews call out that a big pie easily covers multiple meals, especially when paired with a starter.

The sauce and cheese quality show up in each bite, which matters at this price tier. Consider it a splurge you can stretch, not a one-and-done.

Pro tip: Ask your server about half-bake or reheating guidance to maximize leftovers at home. That small step protects your investment and keeps the crust in good shape.

If you are feeding a mixed group, order a thin crust alongside deep dish to balance budget and timing. The net effect is high-value comfort, plated with care.

Hours, Wait Times, And Best Times To Visit

Planning pays off at Hillary’s, because deep dish is not a sprint. The restaurant lists hours on the website and door, with Google noting Thursday open from 12 PM to 9 PM at the time of writing.

Schedules can change, so a quick phone call to +1 904-209-5960 is the safest move, especially on holidays or during local events. Early lunch or late afternoon windows tend to be the smoothest if you are hoping to skip peak waits.

Dinner rush fills the small room fast.

Build in a 45 to 60 minute cushion for deep dish bakes. If you have kids or a tight timeline, order a thin crust to arrive earlier or try the deep dish slice when available.

Staff are upfront about pacing and will help stage appetizers to keep everyone happy. For takeout, consider calling ahead and arriving at the quoted pickup time to avoid idle minutes at the counter.

Parking is typically manageable, though the plaza can get lively. Weather rarely interferes with the plan, since most of the experience is indoors.

With a few expectations set, the wait becomes part of the fun. Let the clock work while the oven does the heavy lifting.

Tips For First-Timers And Unique Features

First time at Hillary’s Ask at the counter about bake times and portion sizes before choosing your pie. If deep dish is your mission, start with an appetizer and settle in.

That hour becomes part of the ritual. The team will remind you to let the pizza rest, which keeps the layers neat and the crust crisp.

For quicker eats, grab slices at lunch or go tavern-thin for a faster turnaround. Leftovers are a feature, not a bug, and reheat nicely.

Unique touches include Chicago-sourced sausage, a sauce locals rave about, and that rare combination of deep dish and thin crust done with equal care. Italian beef brings another taste of home for Midwestern transplants.

The room’s size adds to the camaraderie, and the staff’s menu walk-through makes newcomers feel set up for success. Ask about recommendations if you are undecided.

Travelers can pin the exact GPS coordinates 29.863569, -81.3220376 for easy navigation. Check the website for updates and specials before you roll in.

If the place is hopping, consider takeout or call ahead for timing. With a little planning, your first visit reads like a seasoned regular’s playbook, minus the trial and error.