Welcome to
Hillary's Chicago Pizza
St. Augustine's best, ready to come to you
Bring Chicago to Your Party!
Hillary’s Chicago Pizza food trailer brings authentic Chicago favorites to tailgates, private parties, corporate events and celebrations throughout Northeast Florida—and beyond for select events.
BOOK HILLARY’S FOR:
Chicago Tailgates
Bears games, watch parties & Chicago sports events
Private Parties
Birthdays, graduations, anniversaries & neighborhood parties
Corporate Events
Employee appreciation, office lunches & customer events
Breweries & Pop-Ups
Bring Chicago food to your customers
HOA & Community Events
Neighborhood nights, apartment communities & resident events
Festivals & Large Events
Fast, crowd-friendly Chicago favorites
Not Just Another Food Truck.
A Little Piece of Chicago on Wheels.
Born from our love of Chicago food, sports and neighborhood gatherings, Hillary’s Chicago Pizza brings the flavors of home to Florida. Our trailer turns an ordinary event into a Chicago experience—with the pizza, Italian beef and game-day food we grew up loving.
CHICAGO PIZZA • ITALIAN BEEF • MEATBALLS • CHICAGO FAVORITES
Depending on your event, guest count and service style, menus can feature Hillary’s favorites like:
Chicago Tavern-Style Pizza
Deep Dish Pizza
Italian Beef
Italian Sausage
House-Made Meatballs
Chicago-Style Sandwiches & Sliders
Salads & Sides
Desserts
We’ll help you choose a menu that works for your crowd, service time and budget.
Booking Hillary's is Easy
1 — Tell Us About Your Event
Date, location, guest count and what you're planning.
2 — We'll Build Your Package
We'll recommend a menu and service style based on your crowd and budget.
3 — We Bring Chicago to You
We arrive, set up and serve your guests from the Hillary’s trailer.
Based in St. Augustine. Ready to Roll.
Regular service area:
St. Augustine • St. Johns County • Ponte Vedra • Nocatee • Jacksonville • Northeast Florida
Then make your larger-event positioning clear:
Planning something farther away?
For qualifying events, Chicago tailgates and larger bookings, Hillary’s can travel beyond Northeast Florida.
Tampa • South Florida • Orlando • Select Southeast Events
FAQ
How many people can you serve?
From backyard parties to large Chicago tailgates, Hillary's food trailer can accommodate events from approximately 40 to 300+ guests. For larger events, we'll customize the menu, staffing and service format to keep lines moving and food coming out hot
Is there a minimum to book the trailer?
Yes. Private food trailer bookings have a $700 minimum, which applies toward food and service. Minimums may vary based on event size, location, travel distance, date, and service requirements.
How far will the trailer travel?
Hillary's Chicago Pizza is based in St. Augustine and regularly serves St. Johns County, Jacksonville and Northeast Florida. We love a good road trip! For larger private events, festivals and Chicago sports tailgates, we're available to travel throughout Florida and to select destinations across the Southeast. Travel fees and event minimums may apply based on distance.
Can we choose our menu?
Absolutely! We’ll work with you to create a menu that fits your event, guest count and budget. Choose from Hillary’s favorites like Chicago tavern-style pizza, Italian beef, Italian sausage, house-made meatballs and other Chicago-inspired favorites. For larger events, we may recommend a streamlined menu to keep service fast and lines moving.
Do you cater Bears and Chicago sports events?
Chicago sports are our specialty! Hillary’s Chicago Pizza brings an authentic taste of Chicago to Bears tailgates, watch parties, fan club gatherings, alumni events and Chicago-themed celebrations. From tavern-style pizza and Italian beef to other Chicago favorites, we’ll help create a game-day menu your crowd will love.
Planning a larger Bears event or road-game weekend? We travel for select events throughout Florida and the Southeast. Ask us about bringing Hillary’s Chicago Pizza to your next Chicago tailgate!
What do you need from the event location?
We’ll need a safe, level space for the trailer with enough room to pull in, set up and operate. Depending on your event, we may also need access to electricity and water. Before your event, we’ll confirm parking, access, setup requirements and any venue restrictions with you. Not sure if your location will work? Send us the details—we’re happy to help figure it out.
