The Windy City On Wheels
About The Windy City On Wheels
The Windy City On Wheels is a restaurant located in St. Augustine, FL, known for authentic Chicago-style food, including Italian beef sandwiches, Chicago dogs, and Polish sausages. Customers highlight the generous portions and genuine flavors that reflect classic Chicago cuisine. The staff are frequently described as friendly and attentive.
Reviews emphasize the quality and freshness of the menu items, with particular praise for the Italian beef and hot dogs, often regarded as some of the best in the area. Patrons also appreciate additional touches such as complimentary sauces and sides. The restaurant has gained recognition for replicating Midwest flavors outside of Chicago, making it a recommended choice for those seeking regional specialties in St. Augustine.
Menu Highlights
Hot Dog
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This is the real deal....if you are from the Chicago area it is a must do! If you aren't familiar with our style of Hotdogs, Polish Sausages or Italian Beefs...they won't disappoint.
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I’m from Chicago and lived there for all of my childhood + high school years, but moved to St. Augustine for college and stayed down here after graduating. Being from Chicago, food is something that stays with you and becomes who you are. I miss it all the time and think about it often. I got the chance to try this food truck, and Jason + staff hit it on the head. Beef was outstanding and so was my Chi Style dog. Sometimes you don’t have to travel home to find home. Thanks guys! Hope to eat again soon.
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Italian beef is one of my favorites and this one was phenomenal! I ordered it wet and they even gave me a free sauce on the side! They are not stingy with their servings…full of delicious meat. Can’t wait to have you guys here at Entrado again.
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Chicago dog and Beer brat were 100% the best hot dog ever. The flavor, freshness, and just the whole dang thing was amazing...That is alot to say about a hot dog. Theses are not just hot dogs at all...They are "The Best dang hot dog we have eaten "...Awesome Dogs! Thank you! Until next time!
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Jason and Michele promised us delicious dogs and they didn’t lie! We ordered chili cheese dogs and a Signature J&M dog and we wanted to go back for more. I haven’t had my hot dog snap like that in a long time and I can’t leave the cheese curds off my review either. Best curds I’ve had outside of the Midwest. Come back and visit our neighborhood again! We will definitely go back!
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I got the cheesesteak sandwich which was delicious, and had ton of flavor. The cook and the two ladies were very friendly and even gave us free Italian ice. 10/10 recommend.
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Owners are absolutely AMAZING! So nice to get a taste of back home, and there's nothing like this that I've seen around here! Great food, top notch experience, and super surprised they're brand new! Feels like home, and family, you couldn't tell me they haven't been at this for years! I'll be telling EVERYONE about Windy City on Wheels! This is a stop not to be missed! Our favorites are dogs, Italian beef, & my husband LOVES the chili cheese fries, smash burgers and elephant ears!
Frequently Asked Questions
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What are some popular dishes at The Windy City On Wheels?
The Italian beef, Chicago dogs, and bratwursts are customer favorites known for their authentic Chicago-style flavors.
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Can I dine in or should I order takeaway?
You can choose to dine in, order takeaway, or use kerbside pickup and no-contact delivery options.
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Does The Windy City On Wheels accept reservations?
Yes, they accept reservations to help you plan your visit.
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Is parking available at the restaurant?
Yes, there is free street parking as well as a free parking lot available for customers.
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Is the restaurant wheelchair accessible?
Yes, The Windy City On Wheels has a wheelchair-accessible entrance and car park.
Nearby Restaurants
St Augustine Fish House & Oyster Company
160 Nix Boat Yard Rd St Augustine, FL 32084 United States
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The Italian Beef’s were delicious, true Italian beef. I didn’t eat the Chicago dog and brat but my boyfriend said they were the best. Friendly folks. Had to wait a bit but worth it