The Windy City on Wheels

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!

09/14/2026

🚨 WINDY CITY ON WHEELS IS LOOSE AGAIN THIS WEEK! 🚨

Apparently nobody has learned their lesson, so we’re firing up the truck FOUR DAYS THIS WEEK. 😂🌭🥩

Bring your appetite, your stretchy pants, and that one friend who says “I’m just gonna get something small” and then steals everybody’s fries.

📍 TUESDAY, SEPTEMBER 15 | 11–2 PM
Deerwood North
4601 Touchton Park Rd • Jacksonville, FL 32216
👉 Because a sad desk lunch should be illegal.

📍 WEDNESDAY, SEPTEMBER 16 | 5–8 PM
Oakbrook Neighborhood
3290 Kings Rd • St. Augustine, FL 32086
👉 Cooking dinner is overrated. We already did it for you.

📍 THURSDAY, SEPTEMBER 17 | 5–8 PM
Silverleaf Village Neighborhood
218 Silver Forest Dr • St. Augustine, FL 32092
👉 Silverleaf… prepare yourselves. Chicago is coming. 😂

📍 FRIDAY, SEPTEMBER 18 | 5–8 PM
Bartram Springs Neighborhood
14530 East Cherry Lake Dr • Jacksonville, FL 32258
👉 It’s Friday. Calories don’t count after 5 PM. We checked. 🤷‍♂️

🔥 ITALIAN BEEF. CHICAGO DOGS. BURGERS. FRIES. AND QUESTIONABLE SELF-CONTROL. 🔥

And remember our highly sophisticated company philosophy:

💦 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 HUNGRY FRIENDS & SHARE THIS POST!
Especially the one who says “I’ll just have a bite.”
That person cannot be trusted. 😂

09/09/2026

WARNING: CHICAGO FOOD HAS ESCAPED INTO FLORIDA. 🚨

Windy City On Wheels is rolling out this week, and once again we’re doing our part to make sure nobody in St. Johns County has to eat a sad-ass dinner. 😂

🌭 WEDNESDAY — SEPTEMBER 9 | 5–8 PM
📍 The Peninsula Condos
1431 River Place Blvd
Jacksonville, FL 32207

🔥 FRIDAY — SEPTEMBER 11 | 5–8 PM
📍 Nocatee Station Field
400 Nocatee Center Way
Ponte Vedra, FL 32081

Come hungry. Wear stretchy pants. Cancel whatever responsible dinner plans you had.

We’ll bring the Italian Beef, Chicago Dogs, burgers, fries, and enough bad dietary decisions to make your bathroom scale file a restraining order. 😂

And remember…

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 the friend who always says “I’m not that hungry” and then eats half your damn fries. 😂

09/01/2026

🚨 ST. AUGUSTINE & ST. JOHNS — DINNER PLANS JUST GOT A LOT LESS RESPONSIBLE. 🚨

This week, Windy City On Wheels is rolling into two neighborhoods with enough beef, fries, cheese, and bad dietary decisions to make your scale file a complaint. 😂

📍 THURSDAY, SEPTEMBER 3 • 5–8 PM
🏡 Bannon Lakes Neighborhood
435 Bannon Lakes Blvd
St. Augustine, FL 32092

📍 FRIDAY, SEPTEMBER 4 • 5–8 PM
🏡 Beacon Lakes Neighborhood
850 Beacon Lake Pkwy
St. Johns, FL 32259

🔥 THIS WEEK’S SPECIALS

THE CHICAGO DUMPSTER FIRE — $16
Loaded fries piled with chopped Italian beef & sausage, grilled peppers & onions, hot cheese sauce and giardiniera.

Basically, if Chicago had a yard sale in a bowl, this would be it. 😂

DIET STARTS MONDAY — $15
Shaved steak, grilled peppers & onions, hot cheese sauce, crispy fries and a mayo & ketchup drizzle.

Because putting the fries on the side was just way too mature.

👊 TEAMWORK MAKES THE DREAMWORK!

You bring the family.
You bring the neighbors.
We’ll bring the food that makes everyone say, “I probably shouldn’t… but give me one anyway.” 😎

🌆 WINDY CITY ON WHEELS
Authentic Chicago Food. Big Flavor. Big Attitude.

📲 Tag your food crew, share this post, and come hungry.

It’s not the size of the sandwich… it’s how wet you get it! 🔥