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Winchester Flights as Low as $189
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Cheap Flights to Winchester
Fall in love at first flight with your vacation to Winchester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winchester on Hotwire, and you’ll be up, up, and on a getaway in no time.
Because once the wheels are down in Winchester, the good times start rolling. So buckle up, you’re in for a fun ride.
Frequently Asked Questions About flights to Winchester
Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.
So all you have to worry about is where you’re headed after the LEX airport.
What is the cheapest month to fly to Winchester?
Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winchester are in August, but when you book your flight on Hotwire, savings are always in season.
How many airlines fly to Winchester?
Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Winchester.
What airport is best to fly into Winchester?
When you’re planning your trip to Winchester, convenience is the name of the game. Luckily, Winchester Blue Grass Airport is nearby so you can deplane and get going on checking off everything on your Winchester must-do list.
How much are flights to Winchester?
Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $189, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.
How to get cheap flights to Winchester?
The trick to saving a stack of cash on your flight to Winchester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $189 right now, why wait?
Destination airport | Blue Grass |
|---|---|
Destination airport IATA code | LEX |
Roundtrip price | $189 |
Last Minute Hotel Deals in Winchester
Best Western Winchester Hotel
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.
Reviewed on Dec 14, 2025
Hampton Inn Winchester
Overall the hotel was good - very friendly staff, safe area, clean and presentable. I was quite surprised and astonished by the $75 pet fee - it is outrageous for adding a dog to add $75 to a $150 room. This also was not clearly presented during the booking process.
Reviewed on Jan 4, 2026
The Manchester
Great place to stay, eat and drink.
Reviewed on Jan 20, 2026
Spark by Hilton Lexington Hamburg
Very clean room and great amenities.
Reviewed on Jan 17, 2026
DoubleTree Suites by Hilton Hotel Lexington
Clean room love this place
Reviewed on Jan 17, 2026
Hyatt Regency Lexington
clean room, friendly staff amenities are great
Reviewed on Jan 19, 2026
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
A very nice hotel
Reviewed on Jan 20, 2026
Embassy Suites by Hilton Lexington/UK Coldstream
Location is great Rooms are nice Breakfast is fabulous and staff is very friendly The only problem we’ve experienced in our 3 stays was parking while a conference was in the building. Every spot was double parked and when we asked we were told to find someplace in the grass and that we would have ...
Reviewed on Jan 18, 2026
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