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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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    2 years ago

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    2 years ago

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    2 years ago

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    1 year ago

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    4 years ago

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    2 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

    (150 reviews)

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    Horizons West / West Orlando

    Michael's Ali Coal Fired Pizza, located inside Plant Street Market, downtown Winter Garden is a…read moregreat place if you are looking for pizza. Their menu is pretty large and they cook their items in the coal fire pizza oven. I like that since it gives it that crispy crunchy pizza. Their location is inside Plant Street which has a ton of food places. The best thing about Plant Street is that everyone can get what they want. There are tables throughout Plant Street and Michael's Ali Coal Fire has a few bar seats at their location as well. They specialize in pizza but do have additional options such as stromboli's, wings, and sandwiches. There are some specialty pizzas on their menu but you can also create your own, which is what we did. Next time we will probably go with a specialty pizza just to try it out, but we went with pepperoni and bacon. It was also topped with a little basil. The bacon was pretty much nonexistent but it did have a slight saltiness to it, so I'm sure it was there. My wife loves bacon on her pizza so she definitely wished there was more of it. Overall it was a great pizza. We actually ordered it to take home since we had already had some food at Plant Street. However, it was good and hot and fresh, we ate the entire thing. The pizza is not overall large, I think about 6-7 slices. We shared since we were trying a lot of things. The crust was also really crispy, and not overly charred as sometimes coal fire pizzas can get. Another item we wanted to try but were too full, was the Cheesy Bread which has Roasted Garlic Oil fired with Prosciutto, Mozzarella, Provolone & Gorgonzola. We saw someone else get it and it really looked delicious, very cheesy and really good. The team who works here is also really nice. They were friendly, let us take our time, offered to answer any questions and were just nice. They had a little game going and would ask a question as you paid. They were keeping track of answers. Overall, this is a great spot. I would come back anytime we felt like a pizza. Very great food! ACES!

    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.

    Pinotti's Pizza - Wings

    Pinotti's Pizza

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    Horizons 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.

    The Hangry Bison - Short rib burger

    The Hangry Bison

    (412 reviews)

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    Horizons West / West Orlando

    I had to go to my favorite burger restaurant after my spill last week. It was perfect to go on a…read moreSunday evening as there was no crowd. I was seated immediately when I arrived. My server suggested the smoked old fashioned (17 dollars) to cure my blues. It sure did with the light smoked flavor, yet strong enough to let my happy and relaxed. Since I am trying to avoid beef, I took the dependable sockeye salmon burger with salad (16 dollars). The salmon had the great flavor and was plentiful. It tasted fresh and healthy. The tomato, lettuce, and onion were fresh as well and the mustard complimented the burger nicely. My salad was wonderful and the vinaigrette was such a nice addition. I couldn't leave without dessert, and the ole reliable creme brulee (10 dollars) had a creamy custard with a great shell. It was so enjoyable. The service was great, and while the atmosphere was a bit quieter, I still didn't feel lonely at all. I wish I was able to go to the fountain area afterwards, but the rain and storm had be back to the free garage immediately. The Hangry Bison is still my favorite place for burgers. If only there was a bison to hop on in the restaurant, it would have been much friendlier than the bull last week. It's still a great and underrated burger restaurant in downtown Winter Garden. Overall: A

    The food was good. It was a busy Sunday afternoon and I give them credit for that…read more The server left something to be desired. There were big dogs with their owners inside the restaurant. I like dogs, but not around my food when I'm eating.

    Chicago Stop - italian - Updated May 2026

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