Search Cheap Flights to
Winchester

Photo by Hyelsinta

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winchester Flights as Low as $198

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Delta
Delta
American Airlines
American Airlines
Delta
American Airlines
Delta
Delta
Delta
Bargain Flight
American Airlines
American Airlines
Delta
United
United

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.

Just the right flight

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.

Frequently Asked Questions About flights to Winchester

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 $198, 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 $198 right now, why wait?

Can I fly to Winchester right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Winchester Flight Information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Roundtrip price
$198

Last Minute Hotel Deals in Winchester

GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
The price is $71 per night from Jun 23 to Jun 24
$71
per night
Jun 23 - Jun 24
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,008 reviews)
"Very nice and affordable"

Reviewed on Jun 19, 2024

GuestHouse Lexington
GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
The price is $93 per night from Jun 30 to Jul 1
$93
per night
Jun 30 - Jul 1
Stay at this 3-star hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.2/10 Wonderful! (2,274 reviews)
Mostly great
"After a long day it would be nice to be able to watch a movie. The television programming availability was a big disappointment. The pool was also a disappointment. Very small and uninviting and full of loud children."

Reviewed on Jun 21, 2024

GLō Best Western Lexington
Embassy Suites by Hilton Lexington Green
Embassy Suites by Hilton Lexington Green
3.5 out of 5
245 Lexington Green Circle, Lexington, KY
The price is $127 per night from Jun 30 to Jul 1
$127
per night
Jun 30 - Jul 1
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,003 reviews)
"I was pleasantly surprised. The staff was friendly, and was attentive and available at the desk. The breakfast was fantastic."

Reviewed on Jun 19, 2024

Embassy Suites by Hilton Lexington Green
Marriott Lexington Griffin Gate Golf Resort & Spa
Marriott Lexington Griffin Gate Golf Resort & Spa
4.5 out of 5
1800 Newtown Pike, Lexington, KY
The price is $86 per night from Jun 30 to Jul 1
$86
per night
Jun 30 - Jul 1
Book a stay at this spa resort in Lexington. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (207 reviews)
"-"

Reviewed on Jun 16, 2024

Marriott Lexington Griffin Gate Golf Resort & Spa
Quality Inn Lexington -Horse Park
Quality Inn Lexington -Horse Park
2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
The price is $71 per night from Jun 24 to Jun 25
$71
per night
Jun 24 - Jun 25
Book a stay at this golf hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (1,023 reviews)
"Very nice and the price was perfect"

Reviewed on Jun 21, 2024

Quality Inn Lexington -Horse Park
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
The price is $144 per night from Jul 2 to Jul 3
$144
per night
Jul 2 - Jul 3
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (394 reviews)
"Great place will stay here again. Very clean"

Reviewed on Jun 19, 2024

The Manchester
21c Museum Hotel Lexington
21c Museum Hotel Lexington
4 out of 5
167 West Main Street, Lexington, KY
The price is $139 per night from Jun 24 to Jun 25
$139
per night
Jun 24 - Jun 25
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
8.8/10 Excellent! (894 reviews)
"The staff was very friendly and even though we are from Lexington, our experience felt as if we were taking an out of town trip. The check in desk agent upgraded our room when we mentioned we were out for our anniversary, such a wonderful surprise!"

Reviewed on Jun 21, 2024

21c Museum Hotel Lexington
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
The price is $131 per night from Jun 30 to Jul 1
$131
per night
Jun 30 - Jul 1
Book a stay at this business-friendly hotel in Lexington. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (1,000 reviews)
"Right in heart of Lexington. Close to everything. Room was large and clean."

Reviewed on Jun 11, 2024

Hilton Lexington/Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.