The Windy City on Wheels

The Windy City on Wheels Bringing a Little taste of Chicago to the communities.

06/10/2026

Come join us this Friday from 5-8 in Beacon Lake neighborhood at 850 Beacon Lake Pkwy St John’s. We will be serving our famous Italian Beef sandwiches, Chicago dogs, Cheesesteak sandwiches, Maxwell St Polish and the original pizza puff as well as many more items. Hope to see ya’ll!

06/02/2026

Hello everyone hope to see you this Friday night from 5-8 at Trailmark community in World of Golf 805 Trailmark Dr. we will be serving our famous Italian beef sandwiches, cheesesteaks, smash burgers , Chicago dogs, Maxwell polish and many more. Have a great week!!

05/21/2026

We are back up and running finally! We will be in John’s Island Silverleaf neighborhood on Memorial Day 5-25 from 11-2 in front of the amenity center 501 John’s Island Pkwy St Augustine. Please come out to celebrate your Memorial Day with one of our famous Italian beef sandwiches or a Chicago dog! We would love to see ya’ll so let’s make it a happy and safe Memorial Day!

05/09/2026

We would like to apologize for not making it to Heritage Landing tonight unfortunately we had mechanical issues in our way there. We had a fuel like burst while driving on the highway. We will be up and running soon and look forward to seeing you all!

05/06/2026

Hope ya’ll are having a great week so far and will come out and see us this Friday night in Heritage Landing from 5-8 located at 370 Heritage Landing Pkwy St Augustine. We will be serving our famous Italian beef sandwiches, Combos, Chicago dogs, cheesesteak sandwiches and much more!! Looking forward to seeing you all soon!

04/14/2026

Hello everyone hope you are having a good week so far! We will be downtown St Augustine this Saturday night from 6-9 pm at Peace Pie located at 131 King St. please come and get one of our famous Italian beef sandwiches or Chicago dogs! We also will be serving our delicious smash burgers along with some specials. Hope to see everyone this Saturday and once you are done getting some great Chicago food you can grab dessert at Peace Pie Ice Cream sandwiches they are fantastic!!

03/31/2026

Hello everyone I hope you are having a great week so far!! We will be in Wells Creek neighborhood this Saturday night from 5-8pm at 13580 Holsinger Blvd JAX. Please come join us for a famous Italian Beef Sandwich as well as one of our delicious smash burgers or a Maxwell St Polish!! Hope to see ya’ll there!!

03/26/2026

Hello everyone! We will be at Bartram Springs neighborhood this Saturday 3-28 from 11-2 address 14530 East Cherry Lake Dr Jacksonville. Please come out and get one of our famous Italian beef sandwiches or a Chicago dog. We will be serving some specials as well so hope to see all of you there!

02/19/2026

Hello everyone hope you are having a great week so far! Please come see us tomorrow night at 140 Landing St in St John’s Rivertown neighborhood from 5-8pm. We will be serving our famous Italian beef sandwiches, Chicago dogs, Jasons signature cheesesteaks and some specials you will have to check out! Hope to see you all tomorrow night!!

01/29/2026

Hope everyone is having a great week and staying warm!! We will be at Nocatee Station Field tomorrow night 1-30-26 from 5:30-8:00 pm address 400 Nocatee Center Way. Please brave the cold and come out to see us and get one of our famous Italian Beef Sandwiches or a Jason’s signature Cheesesteak!! We are running some great specials too so come check it out look for to seeing you!

Address

Saint Augustine, FL
32092

Telephone

+19045400045

Website

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