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Winchester Flights as Low as $222
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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 February, 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 12 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 $222, 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 $222 right now, why wait?
Destination airport | Blue Grass |
|---|---|
Destination airport IATA code | LEX |
Roundtrip price | $222 |
Last Minute Hotel Deals in Winchester
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
The Manchester was a great experience. Its location is ideal. Unfortunately my stay was brief, checked in late and slept until right before checkout. I can only speak to the comfort of the rooms, which was excellent, and the courteousness of staff, also excellent. The atmosphere and ambiance are ...
Reviewed on Feb 5, 2026
Hilton Lexington/Downtown
Nice quiet room. Staff were very helpful.
Reviewed on Jan 16, 2026
DoubleTree Suites by Hilton Hotel Lexington
Very cool hotel, good amenities, clean, spacious good price really enjoyed it
Reviewed on Feb 2, 2026
Hyatt Regency Lexington
Nice hotel but looks outdated.
Reviewed on Feb 2, 2026
Elwood Hotel & Suites
Very clean and spacious rooms and the beds were very comfortable! Would definitely recommend.
Reviewed on Feb 2, 2026
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Friendly staff, clean room, comfy bed
Reviewed on Feb 2, 2026
Home2 Suites by Hilton Lexington Hamburg
It was very clean. The staff at the desk, I can't remember the lady's name, was phenomenal. Was offered a room upgrade so I didn't have to use the pull out couch afterall. I appreciated that greatly. As for the rooms themselves, so spacious and well-equipped. Very convenient location with a lot of ...
Reviewed on Jan 24, 2026
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