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    Chicago Stop

    4.1 (8 reviews)

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    Chicago Stop
    Nick G.

    As a Chicagoan now living in Winter Garden, I am always looking for some true Chicago style hot dogs and beefs. Yes we do have a Portillos here now but I had always thought a small Chicago style shop with Dogs and beefs would make a killing. I had the beef today, baptized.....it was absolutely authentic!! The dogs are spot on as well!! I will ALWAYS order from here when I am at plant street!

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    3 years ago

    Helpful 8
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    3 years ago

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    2 years ago

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    2 years ago

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    4 years ago

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    3 years ago

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    3 years ago

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    4 years ago

    Outstanding Chicago hot dogs. I very pleasant surprise here in Winter Garden. I'll definitely come back.

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    Michael's Ali Coal Fired Pizza

    Michael's Ali Coal Fired Pizza

    3.9(153 reviews)
    0.0 miHorizons West / West Orlando
    $$

    We visited this spot on the weekend and my grandson wanted pizza. We place or order and it was done…read morein about 10-15 minutes. My grandson really liked the pepperoni pizza he ordered. The crust was crunchy and the sauce and cheese were good.

    Michael's Ali Coal Fired Pizza is located inside Plant Street Market in downtown Winter Garden. It…read moreis a local pizza spot serving really great food. They actually have a really large menu for a small spot. They are closer to Crooked Can. There are some seats at their spot (similar to bar seats), but most people get their food to go and eat around Plant Street. Plant Street is a market that has tons of permanent vendors, most of which are food. This spot is truly Italian specializing in pizza but there are other options as well. Some of those options include stromboli's, wings, and sandwiches. They have a few different specialty pizza selections but then you can also create your own. We like to create our own but all their specialty pizzas sounded absolutely delicious. Next time, I think we will pick one of the specialty ones. We went with just pepperoni and bacon. The bacon was hardly present but did give a nice saltiness to the pizza. The pizza was on the thinner side which I love, it was crispy on the edges and just a really great pizza. We actually ordered it with the intention of taking it home for the next day, but it was so good, we ended up eating it all that night. Something we wanted but we were so full from other food options at Plant Street was the CHEESY BREAD which has Roasted Garlic Oil fired with Prosciutto, Mozzarella, Provolone & Gorgonzola. This is something we will for sure be getting next time. It sounded so great! For pizza we will be getting the BUFFALO CHICKEN which is Hot Wing Sauce Base, Roasted Chicken, Gorgonzola, Provolone, Mozzarella...Finished with Celery. Their options are just really great. The servers were super friendly as well. They will take your phone number and text you when its ready. This way you can go walk around, grab a table, grab a beer from Crooked Can and wait for your food. This is definitely a spot you need to try out when you are at Plant Street! Great food, great employees and a fun atmosphere.

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    Michael's Ali Coal Fired Pizza
    Michael's Ali Coal Fired Pizza
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    Pinotti's Pizza - Wings

    Pinotti's Pizza

    3.6(61 reviews)
    1.0 miHorizons West / West Orlando
    $$

    This is one of the most unique places to get a pizza on the west side. This is my second time…read morecoming to Pinottis and it does not disappoint. Interior feels high-end and the dining experience there is very elevated, but the service and vibes are down to earth. It's just like your classic mom and pop shop only a little fancier feeling. This is a great place for both a date night and a family gathering. I got the large pizza and pal, vegetarian zucchini and half chicken. The staff is really nice to let me know that that's an option and who doesn't love a little variety. Be prepared their prices for a large are a bit up there and this ended up being close to $40. It's definitely delicious and was checking out. Dig In!

    Pinotti's Pizza isn't just a local favorite in Winter Garden; it's a culinary experience waiting to…read morebe discovered. This independent pizzeria consistently tops the charts as one of the most popular spots in the city, and a single bite reveals exactly why locals are so loyal. Forget the chains and immerse yourself in the authentic taste of Winter Garden by trying their acclaimed dishes. Whether you're a long-time resident or just passing through, a visit to Pinotti's promises new favorite flavors and a true taste of local pizza perfection. Pinotti's Pizza no es solo un favorito local en Winter Garden; es una experiencia culinaria por descubrir. Esta pizzería independiente encabeza constantemente las listas como uno de los lugares más populares de la ciudad, y un solo bocado revela exactamente por qué los lugareños son tan fieles. Olvídate de las cadenas y sumérgete en el auténtico sabor de Winter Garden probando sus aclamados platos. Ya seas residente de toda la vida o solo estés de paso, una visita a Pinotti's te promete nuevos sabores favoritos y una auténtica experiencia de pizza local.

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    Chicago Stop - italian - Updated September 2026

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