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.
Customers consistently praised the friendly and attentive service from staff, with specific mentions of servers like Jacob, Mason, and Sofi.
Food Experience
While many enjoyed the unique flavors of the chili, some found it bland or not to their taste, indicating a mixed reception regarding the food.
Cleanliness
The restaurant was frequently noted for its cleanliness and inviting atmosphere, contributing positively to the overall dining experience.
Nostalgia Factor
Many customers appreciated the nostalgic connection to Cincinnati, expressing happiness to find a Skyline location in Orlando.
Portion Sizes
Several reviews mentioned that portion sizes were smaller than expected, leading to some dissatisfaction regarding value for money.
SC
S Cochran
2 days ago
5.0
We always visit this location when in the Orlando area, usually 2 or 3 times. lol. So glad It’s here. I have great experiences and great meals and love the Cincinnati nostalgia it brings. Today I met the owner, great guy. Great job Daniel, see you again soon!
AR
Addison Ricca
6 days ago
5.0
This was my first time, and the server Samantha was very welcoming and accommodating. She explained the menu in detail so I could get exactly what I was looking for. Great customer experience!
KR
K R
Dec 27, 2025
2.0
First time to a Skyline Chili. Wife feeling under the weather so I offered to get her some chili.
Ordered the Chili Bowl online for takeout. I had high hopes since I saw they had a 4.7 rating. I was greeted as I walked through the door. Staff was super friendly. Restaurant looked clean and had a decent atmosphere. Grabbed the takeout bag and headed home. Thought I had done good!
Get home and watch as my wife takes the $11.97 chili bowl out of the bag. Holy moly what a disappointment. It was a small cup. Then she took the lid off and it got even worse. Dang. For $11.97?? The cup was less than half full. Guess it was to make room for the bag o cheese.
She thanked me for taking the 45 minutes round trip to get her some chili but I could tell she was disappointed.
Next time I will just pay 1/3 of the price and stick with Wendy’s at least you get your moneys worth.
JM
Jasmine M
Dec 20, 2025
5.0
This was my family's first time visiting Skyline Chili. My son really wanted pasta and we wanted a quick bite to eat. We have wanted to try this place for a while and we are so happy we did.
We weren't sure what we wanted but Daniel, the owner was so patient and explained what was great on the menu. We took all of his suggestions and it was amazing. The chili has a unique but delicious flavor and the customer service far exceeded our expectations.
5 stars all around! We will definitely be back.
RB
Ron Bryner
Dec 17, 2025
2.0
The host mentioned right away that they serve Mediterranean style chilli. Not sure what that meant but I ordered a chilli cheese dog and a chilito. The cheese on the chilli dog was grated super fine requiring them to use an anticaking agent. I felt it on my tongue right away and it did not add anything pleasant to the experience. The hot dog was very small and unremarkable in flavor. The bun was steamed and it was served quickly and hot. I took one bite of the chilito and called it quits. The restaurant was clean, bright and the staff was polite, professional and everything one could hope for. The Mediterranean chilli is just not my cup of tea. I did not enjoy the food at all. In fact it left an unpleasant after taste that gave me a valid excuse to drink a beer elsewhere.
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.