Search Cheap Flights to
Winchester

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Winchester Flights as Low as $229

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

Delta
Wed, Dec 18 - Wed, Dec 25
BWI
Baltimore Washington Intl. Thurgood Marshall
LEX
Blue Grass
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 18 from Baltimore Washington Intl. Thurgood Marshall to Blue Grass, returning Wed, Dec 25, priced at $229 found 1 day ago
United
Mon, Dec 16 - Wed, Dec 25
BWI
Baltimore Washington Intl. Thurgood Marshall
LEX
Blue Grass
$233 Roundtrip, found 1 hour ago
$233
Roundtrip
found 1 hour ago
Select United flight, departing Mon, Dec 16 from Baltimore Washington Intl. Thurgood Marshall to Blue Grass, returning Wed, Dec 25, priced at $233 found 1 hour ago
American Airlines
Tue, Dec 17 - Tue, Dec 17
IAD
Washington Dulles Intl.
LEX
Blue Grass
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 17 from Washington Dulles Intl. to Blue Grass, returning Tue, Dec 17, priced at $242 found 1 day ago
American Airlines
Mon, Dec 16 - Mon, Dec 16
DCA
Ronald Reagan Washington National
LEX
Blue Grass
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Dec 16 from Ronald Reagan Washington National to Blue Grass, returning Mon, Dec 16, priced at $242 found 1 day ago
American Airlines
Mon, Dec 16 - Tue, Dec 17
IAD
Washington Dulles Intl.
LEX
Blue Grass
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Dec 16 from Washington Dulles Intl. to Blue Grass, returning Tue, Dec 17, priced at $247 found 1 day ago
Delta
Mon, Dec 16 - Tue, Dec 24
BWI
Baltimore Washington Intl. Thurgood Marshall
LEX
Blue Grass
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Dec 16 from Baltimore Washington Intl. Thurgood Marshall to Blue Grass, returning Tue, Dec 24, priced at $248 found 1 day ago
Delta
Wed, Dec 18 - Tue, Dec 24
BWI
Baltimore Washington Intl. Thurgood Marshall
LEX
Blue Grass
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 18 from Baltimore Washington Intl. Thurgood Marshall to Blue Grass, returning Tue, Dec 24, priced at $249 found 1 day ago
Delta
Thu, Feb 6 - Wed, Feb 12
DCA
Ronald Reagan Washington National
LEX
Blue Grass
$299 Roundtrip, found 4 days ago
$299
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Feb 6 from Ronald Reagan Washington National to Blue Grass, returning Wed, Feb 12, priced at $299 found 4 days ago
Delta
Tue, Mar 4 - Tue, Mar 11
SMF
Sacramento Intl.
LEX
Blue Grass
$301 Roundtrip, found 6 hours ago
$301
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Mar 4 from Sacramento Intl. to Blue Grass, returning Tue, Mar 11, priced at $301 found 6 hours ago
American Airlines
Thu, Dec 12 - Sun, Dec 15
PHX
Sky Harbor Intl.
LEX
Blue Grass
$338 Roundtrip, found 1 day ago
$338
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Dec 12 from Sky Harbor Intl. to Blue Grass, returning Sun, Dec 15, priced at $338 found 1 day ago
United
Wed, Dec 11 - Mon, Dec 16
ORD
O'Hare Intl.
LEX
Blue Grass
$377 Roundtrip, found 9 hours ago
$377
Roundtrip
found 9 hours ago
Select United flight, departing Wed, Dec 11 from O'Hare Intl. to Blue Grass, returning Mon, Dec 16, priced at $377 found 9 hours ago
United
Thu, Mar 6 - Tue, Mar 11
MFR
Rogue Valley Intl.
LEX
Blue Grass
$427 Roundtrip, found 6 hours ago
$427
Roundtrip
found 6 hours ago
Select United flight, departing Thu, Mar 6 from Rogue Valley Intl. to Blue Grass, returning Tue, Mar 11, priced at $427 found 6 hours ago
Delta
Thu, Nov 28 - Sat, Dec 7
ONT
Los Angeles - Ontario Intl.
LEX
Blue Grass
$453 Roundtrip, found 2 hours ago
$453
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Nov 28 from Los Angeles - Ontario Intl. to Blue Grass, returning Sat, Dec 7, priced at $453 found 2 hours ago
Delta
Thu, Nov 28 - Sat, Dec 7
SNA
John Wayne
LEX
Blue Grass
$493 Roundtrip, found 6 hours ago
$493
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Nov 28 from John Wayne to Blue Grass, returning Sat, Dec 7, priced at $493 found 6 hours ago
Alaska Airlines
Thu, Dec 12 - Sun, Dec 15
PHX
Sky Harbor Intl.
LEX
Blue Grass
$809 Roundtrip, found 1 day ago
$809
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Thu, Dec 12 from Sky Harbor Intl. to Blue Grass, returning Sun, Dec 15, priced at $809 found 1 day ago
American Airlines
Wed, Nov 27 - Tue, Dec 3
LAX
Los Angeles Intl.
LEX
Blue Grass
$938 Roundtrip, found 6 hours ago
$938
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Nov 27 from Los Angeles Intl. to Blue Grass, returning Tue, Dec 3, priced at $938 found 6 hours ago

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 December, 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 16 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 $229, 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 $229 right now, why wait?

Winchester Flight Information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Roundtrip price
$229

Last Minute Hotel Deals in Winchester

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 $67 per night from Dec 24 to Dec 25
$67
includes taxes & fees
Dec 24 - Dec 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 ...
8.2/10 Very Good! (1,332 reviews)
our room
"bathrooms is tight, had a view of the rooftop from our room, NO BUGS, mostly clean, no real complaints, friendly staff, breakfast alright, would stay again"

Reviewed on Nov 25, 2024

Quality Inn Lexington -Horse Park
GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
The price is $97 per night from Dec 1 to Dec 2
$97
includes taxes & fees
Dec 1 - Dec 2
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! (2,240 reviews)
"We've stayed here three times now and the staff is always super nice, they have funky decor, the pool is great for the kids, they have a nice hot breakfast buffet in the morning, and there's a cracker barrel in the same plaza."

Reviewed on Nov 25, 2024

GLō Best Western Lexington
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
The price is $78 per night from Nov 28 to Nov 29
$78
includes taxes & fees
Nov 28 - Nov 29
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 ...
8/10 Very Good! (1,082 reviews)
"Very friendly staff at check in. I’ve stayed here many times and have always enjoyed my stay. I think for the price it is a great deal. The room was comfortable and clean. There is some wear on the carpet but it’s not bad enough to sway me to stay somewhere else much more expensive."

Reviewed on Nov 25, 2024

GuestHouse Lexington
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
The price is $208 per night from Dec 22 to Dec 23
$208
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. ...
9.4/10 Exceptional! (613 reviews)
"Amazing hotel with great customer service! Restaurant and bar there were amazing. High quality and great smelling body products in room. Beds are way too soft but otherwise perfect couples getaway!"

Reviewed on Nov 24, 2024

The Manchester
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 $146 per night from Dec 8 to Dec 9
$146
includes taxes & fees
Dec 8 - Dec 9
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! (327 reviews)
"We could not adjust the air for heat. Stayed 67 all night. Could not get support period. No one would pick up the phone or was at the lobby desk."

Reviewed on Nov 24, 2024

Marriott Lexington Griffin Gate Golf Resort & Spa
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 $137 per night from Dec 15 to Dec 16
$137
includes taxes & fees
Dec 15 - Dec 16
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! (1,002 reviews)
"Great place to stay."

Reviewed on Nov 17, 2024

Embassy Suites by Hilton Lexington Green
Quality Inn Lexington East/Hamburg Area
Quality Inn Lexington East/Hamburg Area
2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
The price is $64 per night from Dec 24 to Dec 25
$64
includes taxes & fees
Dec 24 - Dec 25
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 pool in ...
7.6/10 Good! (1,007 reviews)
"Wasn't bad. I have stayed at way worse plan on using it again on my next stay."

Reviewed on Nov 25, 2024

Quality Inn Lexington East/Hamburg Area
Hyatt Regency Lexington
Hyatt Regency Lexington
3.5 out of 5
401 W High St, Lexington, KY
The price is $127 per night from Dec 25 to Dec 26
$127
includes taxes & fees
Dec 25 - Dec 26
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,006 reviews)
"If you are going to a UK game this is the only place to stay! No matter the weather you will arrive in great shape. Parking is reasonable for an overnight stay. The staff was all very friendly. The views are nice. We will definitely stay here on our next trip."

Reviewed on Nov 25, 2024

Hyatt Regency Lexington
See all 1,110 properties in Winchester
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.