RestaurantFast Food RestaurantDinerGreek RestaurantSkyline Chili
Skyline Chili restaurant chain. Famous for secret recipe Cincinnati-style chili & fast, friendly dine-in & drive-thru service. Serving Cheese Coneys, Ways, Greek Salad & more great-tasting food since 1949. Locations in OH, KY, IN & FL. Grocery products available at on Amazon and at select grocery stores throughout the US.
I live nearby and from day one the consistency is at best inconsistent. The flavor is always spot on. I think the staff is a bunch of young kids who just dont care. 1/2 the time im given the wrong cheese. Usually I catch it as window now by looking, but yesterday I was in a hurry and didnt check. Well guess what no extreme cheese. On top of that they give you wrong amounts. Usually w a large youngrt 2 small bags or 1 larger bag of cheese. Well I was given a small bag and the wrong cheese. Prep of the food inconsistent as well. Sometimes you get a trsy full of noodles and chili well like yesterday, plenty of noodles barely any 1/2 amount of chili thats normal. Again great place friendly staff just lacking of consistency. The owners are the best but the consistency of the staff is dismal. Id suggest go enjoy but make sure to thoroughly check your order if going thru drive thru. Dont be in a hurry and skip this step. Hahaha. Again food is good and team is friendly.
TB
TACO BURRITO
Apr 13, 2026
5.0
Stop by for a quick bite. The food was amazing and service as well. Clean with lots of space to seat. I had the cheese coney an it fresh super cheesy which is a good thing. Everyone was so friendly. That made my first experience such a great one.
JB
Journey Brown-Saintel
Apr 9, 2026
5.0
Skyline Chili is such a hidden gem! The service was impeccable (they really go above and beyond) and everything we tried on the menu was hit! I’m usually not a fan of chili but this recipe is insane. I also highly recommend the funnel cake fries and the specialty ice cream.
TL
Todd LeDoux
Apr 6, 2026
1.0
I ordered a take out Greek salad 🥗 It didn't come with any salad dressing. All I got was lettuce, tomatoes and olives. That's it! Ridiculous and embarrassing. And when i tried to call to figure out how to pick some up after being home and the online phone number and phone number on the receipt were wrong numbers! Terrible
DS
Dana Schacht
Apr 2, 2026
5.0
Visiting from Wisconsin!!!
Big chili fans and big cheese fans. Put the two together and this is the perfect spot!
Ive never seen cheese piled so high. A good 2 inches off the meal!!!
The shop itself was clean and had a good flow of people traffic. We loved being able to watch our food being made!
Mason was our waitor and he handled our group of 16 wonderfully! He was all smiles and answered every question we had about the menu.
The owner was there too and he was also very nice and helpful!
We left full and happy!
What are the regular dining hours for Skyline Chili in Winter Garden?
Skyline Chili is open for dine-in from 10:30 AM to 12:00 AM every day of the week.
Does Skyline Chili offer drive-thru service and what are its hours?
Yes, Skyline Chili offers drive-thru service daily from 10:30 AM to 1:00 AM.
Where is Skyline Chili located?
Skyline Chili is located at 2231 Western Way #B, Winter Garden, FL 34787, in the Flamingo Crossings Orlando neighborhood.
What type of cuisine does Skyline Chili specialize in?
Skyline Chili is famous for its secret recipe Cincinnati-style chili and offers fast, friendly dine-in and drive-thru service, including Cheese Coneys and Greek Salad.
Does Skyline Chili have options for vegetarians and children?
Yes, Skyline Chili serves vegetarian options and has a children's menu available.
Can I order takeout or catering from Skyline Chili?
Yes, Skyline Chili offers takeout services as well as catering options.
Does Skyline Chili accept reservations?
No, Skyline Chili does not accept or require reservations.
Are there any coffee shops near Skyline Chili where I can get a drink before or after my meal?
Yes, Starbucks and Dunkin' are nearby coffee shops where you can enjoy a coffee before or after visiting Skyline Chili.
What other restaurants are located near Skyline Chili at Flamingo Crossings Orlando?
Nearby restaurants include Pieology at FLAMINGO CROSSINGS Town Center, Firehouse Subs, Domino's Pizza, Wendy's, PDQ Winter Garden, Lime Fresh Mexican Grill, and PITA Mediterranean Street Food.
Are there convenient stores or pharmacies close to Skyline Chili for additional needs?
Yes, CVS Pharmacy, Walgreens, 7-Eleven, and Target are nearby for convenience shopping or pharmacy needs.
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