The Windy City on Wheels

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! 🔥

08/27/2026

Check out the new Windy City Menu!!

08/25/2026

Jason Ransom

🚨 ST. JOHNS COUNTY — PUT THE SALAD BACK IN THE FRIDGE. 🚨

Windy City On Wheels is rolling out this week, and apparently we’ve decided portion control is somebody else’s problem. 😂

📍 WEDNESDAY, AUGUST 26 • 5–8 PM
🔥 Johns Creek Neighborhood
224 Johns Creek
St. Augustine, FL 32092

📍 THURSDAY, AUGUST 27 • 5–8 PM
🔥 Watersong Neighborhood in Rivertown
15 Juniper Hills Dr
St. Johns, FL 32259

And because regular dinner wasn’t dangerous enough, check out this week's lineup:

🔥 THE CHICAGO DUMPSTER FIRE — $16
Fries loaded with chopped Italian beef & sausage, grilled peppers & onions, hot cheese sauce and giardiniera.
Basically, we threw Chicago into a bowl and stopped asking questions. 😂

🤰 DIET STARTS MONDAY — $15
Shaved steak, grilled peppers & onions, hot cheese sauce, crispy fries and mayo & ketchup drizzle.
We put the fries ON the sandwich because putting them on the side seemed way too responsible.

👴 THE OLD SCHOOL BOLOGNA — $7
SMOKED. THEN FRIED.
Crispy edges, yellow mustard and soft white bread.

No aioli.
No brioche.
No microgreens.
No nonsense.

Just the kind of sandwich your grandma would've handed you before telling you to get outside and don't come back until the streetlights come on. 😂😂

And remember...

👊 TEAMWORK MAKES THE DREAMWORK!

You bring the neighbors.
You bring the appetite.
We'll bring the beef, bologna and questionable dietary decisions.

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

📲 TAG YOUR HUNGRY FRIEND. SHARE THIS POST. AND COME SEE US!

It's not the size of the sandwich... it's how wet you get it! 😎🔥

08/25/2026

🚨 ST. JOHNS COUNTY — PUT THE SALAD BACK IN THE FRIDGE. 🚨

Windy City On Wheels is rolling out this week, and apparently we’ve decided portion control is somebody else’s problem. 😂

📍 WEDNESDAY, AUGUST 26 • 5–8 PM
🔥 Johns Creek Neighborhood
224 Johns Creek
St. Augustine, FL 32092

📍 THURSDAY, AUGUST 27 • 5–8 PM
🔥 Watersong Neighborhood in Rivertown
15 Juniper Hills Dr
St. Johns, FL 32259

And because regular dinner wasn’t dangerous enough, check out this week's lineup:

🔥 THE CHICAGO DUMPSTER FIRE — $16
Fries loaded with chopped Italian beef & sausage, grilled peppers & onions, hot cheese sauce and giardiniera.
Basically, we threw Chicago into a bowl and stopped asking questions. 😂

🤰 DIET STARTS MONDAY — $15
Shaved steak, grilled peppers & onions, hot cheese sauce, crispy fries and mayo & ketchup drizzle.
We put the fries ON the sandwich because putting them on the side seemed way too responsible.

👴 THE OLD SCHOOL BOLOGNA — $7
SMOKED. THEN FRIED.
Crispy edges, yellow mustard and soft white bread.

No aioli.
No brioche.
No microgreens.
No nonsense.

Just the kind of sandwich your grandma would've handed you before telling you to get outside and don't come back until the streetlights come on. 😂😂

And remember...

👊 TEAMWORK MAKES THE DREAMWORK!

You bring the neighbors.
You bring the appetite.
We'll bring the beef, bologna and questionable dietary decisions.

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

📲 TAG YOUR HUNGRY FRIEND. SHARE THIS POST. AND COME SEE US!

It's not the size of the sandwich... it's how wet you get it! 😎🔥

08/24/2026

Who remembers there momma’s Cigarette Purse?? Let’s Go!!!!way back .