The Windy City on Wheels

10/19/2026

👻🚨 WARNING: CHICAGO FOOD IS ABOUT TO HAUNT ST. JOHNS COUNTY! 🚨👻🎃

WINDY CITY ON WHEELS IS GETTING SPOOKY THIS WEEKEND! 🌭🥩🔥

Forget the ghosts, goblins, and things that go bump in the night… the REAL horror is showing up hungry and finding out we’re SOLD OUT! 😱😂

We’re rolling into TWO Halloween events this weekend, bringing authentic Chicago food, big flavor, and enough Italian beef to raise the dead! 💀🥩

🎃 FRIDAY, OCTOBER 23 | 6–9 PM 🎃

👻 SILVERLEAF SPOOKTACULAR!
📍 Johns Island
501 Johns Island Pkwy
St. Augustine, FL 32092

Come out for a SPOOKTACULAR evening featuring:

🎡 Rides
🏰 Bounce Houses
🎸 Live Music
🎨 Face Painting
🌭 Delicious Chicago Food & MORE!

Bring the kids, bring the neighbors, bring your appetite! Just don’t blame us when your costume doesn’t fit after dinner! 😂

💀 SATURDAY, OCTOBER 24 | 6:30–9:30 PM 💀

👻 NOC SO SCARY!
📍 Nocatee Station Field
400 Nocatee Center Way
Ponte Vedra, FL 32081

Get ready for a frightfully good time featuring:

🏚️ Haunted House
🐐 Petting Zoo
🎶 Live Music
🚂 Train Rides
🎨 Crafts & MUCH MORE!

Brave the haunted house if you dare… but let’s see how brave you are when we ask if you want your Italian Beef DIPPED! 💦😂

🔥 WHAT’S COOKIN’ IN THE WINDY CITY? 🔥

🥩 Italian Beef — So juicy it’s SCARY!

🌭 Chicago Dogs — No ketchup allowed! That’s the REAL Halloween horror story!

🍔 Smash Burgers — So good they’ll wake the dead!

🔥 Polish Sausage — Bigger than your Halloween candy stash!

🍟 Fries & Cheese Curds — Because nobody ever said, “I wish I ate less cheese!” 😂

And remember our famous motto…

💦 IT’S NOT THE SIZE OF THE SANDWICH… IT’S HOW WET YOU GET IT! 💦

This weekend, the only thing scarier than the haunted house is HOW FAST YOU’LL INHALE THAT ITALIAN BEEF! 😂🥩

🌭 WINDY CITY ON WHEELS
📞 (904) 540-0045

🔥 REAL CHICAGO FOOD. BIG FLAVOR. BIG ATTITUDE. ZERO APOLOGIES!

👇 LIKE • SHARE • TAG YOUR HALLOWEEN CREW!

And if your friend says, “I’m just coming for the kids… I’m not eating anything”…

THAT’S THE BIGGEST LIE SINCE SOMEONE SAID ONE CHICAGO DOG WOULD BE ENOUGH! 😂🌭

🎃 COME FOR THE SCARES. STAY FOR THE BEEF. LEAVE WITH A FOOD COMA! 👻

10/14/2026

🚨🌭 BREAKING NEWS: TAMAYA IS ABOUT TO GET BEEFED UP! 🚨😂

WINDY CITY ON WHEELS IS ROLLING INTO YOUR NEIGHBORHOOD! 🔥

Tamaya, put down the frozen dinners, cancel the DoorDash, and tell your air fryer to take the night off! Chicago is coming to town, and we’re bringing enough beef to make a vegetarian reconsider their entire life. 😂🥩

📅 THURSDAY, OCTOBER 15
⏰ 5:00 PM – 8:00 PM
📍 TAMAYA NEIGHBORHOOD
12788 Meritage Blvd
Jacksonville, FL 32246

🔥 WHAT’S ON THE MENU? 🔥

🥩 Italian Beef — So juicy you’ll need extra napkins and possibly a change of clothes! 💦

🌭 Chicago Dogs — Ketchup? Don’t even think about it. We’re from Chicago, not a crime scene! 😂

🍔 Burgers — Because sometimes you just need to wrap both hands around something delicious!

🔥 Polish Sausage — Big, juicy, and full of Chicago attitude!

🍟 Fries & Cheese Curds — Because cheese makes everything better!

💥 ONE NIGHT ONLY, TAMAYA! 💥

Bring the kids, bring the neighbors, bring your mother-in-law… hell, we’ll even feed her if she promises not to complain! 😂

And remember:

💦 IT’S NOT THE SIZE OF THE SANDWICH… IT’S HOW WET YOU GET IT! 💦

🌭 WINDY CITY ON WHEELS
📞 (904) 540-0045

REAL CHICAGO FOOD. BIG FLAVOR. BIG ATTITUDE. ZERO APOLOGIES! 🔥

👇 LIKE • SHARE • TAG YOUR HUNGRY FRIENDS!

Especially that friend who says, “I’m just gonna have a bite.”

HELL NO, KAREN! GET YOUR OWN DAMN SANDWICH! 😂🌭

10/09/2026

Hello everyone! Sorry to inform you but we will not be working tonight (Nocatee) or tomorrow night (Demons Behind Me Rise Above Fest) at either of our events due to the bad weather coming in everything has been cancelled unfortunately. We hope to see ya’ll next week for some great Chicago food!! Stay safe and dry this weekend!

10/06/2026

10/06/2026

🚨🌭 WINDY CITY ON WHEELS — THIS WEEK’S SCHEDULE! 🌭🚨
We’ve got lunch, dinner, motorcycles, live music, and enough Italian beef to make your cardiologist unfollow us. 😂

THURSDAY, OCTOBER 8 | 11 AM–2 PM
📍 Deerwood Park South
10151 Deerwood Park Blvd
Jacksonville, FL 32256
Lunch plans? Handled. Tell that sad turkey sandwich in the office fridge it can take the day off.

FRIDAY, OCTOBER 9 | 5:30–8 PM
📍 Nocatee Station Field
400 Nocatee Center Way
Ponte Vedra, FL 32081
Nocatee, we’re coming back — hide the diets and bring the stretchy pants.

🔥 SATURDAY, OCTOBER 10 | 4–8 PM — THIS ONE IS SPECIAL! 🔥
📍 Adamec Harley-Davidson
380 Outlet Mall Blvd
St. Augustine, FL 32084

💚 RISE ABOVE FEST: A DAY OF HOPE 💚
Presented by Demons Behind Me Foundation on World Mental Health Day.

🎸 LIVE MUSIC
🌭 FOOD TRUCKS
🛍️ VENDORS
🎟️ AUCTIONS & RAFFLES
🎉 FREE GENERAL ADMISSION

VIP tickets include open bar, food & an event T-shirt, and VIP ticket purchases will help provide therapy sessions to people in need.

Come out Saturday, support an awesome cause, listen to some music, check out the bikes, and then come see us when the smell of Italian beef destroys whatever self-control you had left. 😂

And remember…

💦 IT’S NOT THE SIZE OF THE SANDWICH…
IT’S HOW WET YOU GET IT! 💦

🌭 WINDY CITY ON WHEELS
📞 (904) 540-0045

👇 LIKE • SHARE • TAG YOUR CREW!
Especially your friend who says “I’m eating healthy this week.”
We’d like 30 seconds alone with them and an Italian beef. 😂

RISE ABOVE. SUPPORT THE MISSION. EAT CHICAGO. 💚🏍️🌭

10/02/2026

Sorry due to the inclement weather we will not be at julington creek. Please follow us for updates in future bookings.

09/28/2026

🚨 BREAKING NEWS: FLORIDA HAS BEEN INVADED BY ITALIAN BEEF. 🚨

Windy City On Wheels is rolling out 3 TIMES THIS WEEK, because apparently one day of bad decisions and wet sandwiches just isn’t enough. 😂🌭🥩

📍 WEDNESDAY, SEPTEMBER 30 | 11 AM–2 PM
✈️ BOEING — LUNCH
6225 Lake Gray Blvd, Suite #1
Jacksonville, FL 32244
Come grab lunch. Your sad little sandwich from home will understand.

📍 THURSDAY, OCTOBER 1 | 5–8 PM
🏠 SEVILLA NEIGHBORHOOD
130 Casa Sevilla Ave
St. Augustine, FL 32092
Put the frozen pizza back. Chicago has dinner covered.

📍 FRIDAY, OCTOBER 2 | 5–8 PM
🔥 JULINGTON CREEK PLANTATION
350 Plantation Club Pkwy
St. Johns, FL 32259
It’s Friday. Calories have officially clocked out for the weekend. 😂

We’re bringing the Italian Beef, Chicago Dogs, burgers, fries and enough Chicago attitude to make you forget you're in Florida.

💦 And remember our scientifically questionable motto:

IT’S NOT THE SIZE OF THE SANDWICH…
IT’S HOW WET YOU GET IT. 😂

🌭 WINDY CITY ON WHEELS
📞 (904) 540-0045

👇 TAG YOUR HUNGRY FRIENDS & SHARE!
Especially that friend who says “I’ll just have one bite.”

That lying bastard needs his own sandwich. 😂

09/22/2026

🚨 WINDY CITY ON WHEELS — THIS WEEK’S STOP! 🚨

This week we’re keeping it simple: ONE STOP. ONE SATURDAY. A WHOLE LOTTA CHICAGO. 🌭🥩🔥

📍 SATURDAY, SEPTEMBER 26 | 10 AM–2 PM
TRAILMARK NEIGHBORHOOD — TRAILMARKET EVENT
805 Trailmark Dr
St. Augustine, FL 32092

TrailMark, you’ve got a market… we’ve got the beef. 😂

Come shop, hang out, and grab some authentic Chicago food before we sell out. And remember: walking around the market while eating Italian beef technically counts as exercise. We don’t make the rules. 🤷‍♂️

🔥 ITALIAN BEEF • CHICAGO DOGS • BURGERS • FRIES & MORE 🔥

💦 IT’S NOT THE SIZE OF THE SANDWICH…
IT’S HOW WET YOU GET IT.

📞 (904) 540-0045
🌭 WINDY CITY ON WHEELS
REAL CHICAGO FOOD. BIG FLAVOR. ZERO APOLOGIES.

👇 TAG YOUR TRAILMARK CREW & SHARE THIS POST!
See you Saturday — come hungry, leave questioning your life choices. 😂

09/17/2026

Hello everyone just letting you all know we will be at a different location in Silverleaf tomorrow night due to Silverleaf Village amenity center being closed. You can still come see us and get that great Chicago food in John’s Island at 501 John’s Island Pkwy St Augustine right down the street from the village. Hope to see ya”ll tomorrow night!