Search Cheap Flights to
Winchester

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Winchester Flights as Low as $217

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

Delta
Wed, Feb 12 - Wed, Feb 12
CLE
Hopkins Intl.
LEX
Blue Grass
$217 Roundtrip, found 19 hours ago
$217
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Feb 12 from Hopkins Intl. to Blue Grass, returning Wed, Feb 12, priced at $217 found 19 hours ago
Delta
Fri, Feb 7 - Wed, Feb 12
CLE
Hopkins Intl.
LEX
Blue Grass
$218 Roundtrip, found 19 hours ago
$218
Roundtrip
found 19 hours ago
Select Delta flight, departing Fri, Feb 7 from Hopkins Intl. to Blue Grass, returning Wed, Feb 12, priced at $218 found 19 hours ago
United
Fri, Feb 7 - Thu, Feb 13
CLE
Hopkins Intl.
LEX
Blue Grass
$219 Roundtrip, found 4 days ago
$219
Roundtrip
found 4 days ago
Select United flight, departing Fri, Feb 7 from Hopkins Intl. to Blue Grass, returning Thu, Feb 13, priced at $219 found 4 days ago
United
Fri, Feb 7 - Thu, Feb 13
CLE
Hopkins Intl.
LEX
Blue Grass
$224 Roundtrip, found 4 days ago
$224
Roundtrip
found 4 days ago
Select United flight, departing Fri, Feb 7 from Hopkins Intl. to Blue Grass, returning Thu, Feb 13, priced at $224 found 4 days ago
Delta
Wed, Mar 5 - Sat, Mar 15
MLI
Quad City Intl.
LEX
Blue Grass
$229 Roundtrip, found 18 hours ago
$229
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Mar 5 from Quad City Intl. to Blue Grass, returning Sat, Mar 15, priced at $229 found 18 hours ago
Delta
Fri, Feb 7 - Sun, Feb 9
CLE
Hopkins Intl.
LEX
Blue Grass
$229 Roundtrip, found 19 hours ago
$229
Roundtrip
found 19 hours ago
Select Delta flight, departing Fri, Feb 7 from Hopkins Intl. to Blue Grass, returning Sun, Feb 9, priced at $229 found 19 hours ago
American Airlines
Thu, Jan 23 - Thu, Jan 30
CHO
Charlottesville-Albemarle
LEX
Blue Grass
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jan 23 from Charlottesville-Albemarle to Blue Grass, returning Thu, Jan 30, priced at $234 found 1 day ago
Delta
Thu, Jan 23 - Tue, Jan 28
CHO
Charlottesville-Albemarle
LEX
Blue Grass
$239 Roundtrip, found 2 days ago
$239
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jan 23 from Charlottesville-Albemarle to Blue Grass, returning Tue, Jan 28, priced at $239 found 2 days ago
United
Fri, Feb 7 - Thu, Feb 13
CLE
Hopkins Intl.
LEX
Blue Grass
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select United flight, departing Fri, Feb 7 from Hopkins Intl. to Blue Grass, returning Thu, Feb 13, priced at $245 found 4 days ago
Delta
Wed, Jan 22 - Thu, Jan 30
CHO
Charlottesville-Albemarle
LEX
Blue Grass
$249 Roundtrip, found 2 days ago
$249
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jan 22 from Charlottesville-Albemarle to Blue Grass, returning Thu, Jan 30, priced at $249 found 2 days ago
United
Fri, Feb 7 - Thu, Feb 13
CLE
Hopkins Intl.
LEX
Blue Grass
$250 Roundtrip, found 4 days ago
$250
Roundtrip
found 4 days ago
Select United flight, departing Fri, Feb 7 from Hopkins Intl. to Blue Grass, returning Thu, Feb 13, priced at $250 found 4 days ago
American Airlines
Tue, Jan 21 - Tue, Jan 28
CHO
Charlottesville-Albemarle
LEX
Blue Grass
$254 Roundtrip, found 2 days ago
$254
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jan 21 from Charlottesville-Albemarle to Blue Grass, returning Tue, Jan 28, priced at $254 found 2 days ago
American Airlines
Tue, Mar 25 - Sat, Apr 5
AVP
Scranton Intl.
LEX
Blue Grass
$432 Roundtrip, found 1 day ago
$432
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 25 from Scranton Intl. to Blue Grass, returning Sat, Apr 5, priced at $432 found 1 day ago
American Airlines
Tue, Jan 14 - Sat, Jan 18
CLT
Charlotte-Douglas Intl.
LEX
Blue Grass
$475 Roundtrip, found 1 day ago
$475
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jan 14 from Charlotte-Douglas Intl. to Blue Grass, returning Sat, Jan 18, priced at $475 found 1 day ago
Delta
Mon, Mar 10 - Mon, Mar 17
ANC
Ted Stevens Anchorage Intl.
LEX
Blue Grass
$641 Roundtrip, found 20 hours ago
$641
Roundtrip
found 20 hours ago
Select Delta flight, departing Mon, Mar 10 from Ted Stevens Anchorage Intl. to Blue Grass, returning Mon, Mar 17, priced at $641 found 20 hours ago
Alaska Airlines
Wed, Mar 5 - Tue, Mar 11
ANC
Ted Stevens Anchorage Intl.
LEX
Blue Grass
$882 Roundtrip, found 20 hours ago
$882
Roundtrip
found 20 hours ago
Select Alaska Airlines flight, departing Wed, Mar 5 from Ted Stevens Anchorage Intl. to Blue Grass, returning Tue, Mar 11, priced at $882 found 20 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 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 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 $217, 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 $217 right now, why wait?

Winchester Flight Information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Roundtrip price
$216

Last Minute Hotel Deals in Winchester

GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
The price is $112 per night from Jan 12 to Jan 13
$112
includes taxes & fees
Jan 12 - Jan 13
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! (2,270 reviews)
"Nice room, helpful staff, and good overall value"

Reviewed on Jan 9, 2025

GLō Best Western Lexington
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 $68 per night from Feb 9 to Feb 10
$68
includes taxes & fees
Feb 9 - Feb 10
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! (1,383 reviews)
"This was a safe, convenient, and quiet spot for two quick nights in the Lexington area."

Reviewed on Jan 9, 2025

Quality Inn Lexington -Horse Park
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
The price is $147 per night from Jan 29 to Jan 30
$147
includes taxes & fees
Jan 29 - Jan 30
Stay at this 3.5-star 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! (1,003 reviews)
A great room with a snowy view
"Staff were so helpful and friendly when I stayed here overnight- I am a nurse and needed to stay close to the hospital during a snow storm. Room service was delicious, the bed was so comfortable and the room was delightful. My new downtown Lexington favorite!"

Reviewed on Jan 7, 2025

Hilton Lexington/Downtown
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
The price is $97 per night from Jan 26 to Jan 27
$97
includes taxes & fees
Jan 26 - Jan 27
Stay at this 3.5-star business-friendly hotel in Lexington. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,008 reviews)
"Free drinks and snacks at happy hour and a great breakfast to start the day"

Reviewed on Jan 9, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
The price is $238 per night from Jan 20 to Jan 21
$238
includes taxes & fees
Jan 20 - Jan 21
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! (668 reviews)
"They put a lot of time and consideration into the details and decorations of the rooms. Beautiful. We had dinner at the restaurant and the food was delicious. We will definitely be back."

Reviewed on Jan 7, 2025

The Manchester
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 Jan 19 to Jan 20
$127
includes taxes & fees
Jan 19 - Jan 20
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! (1,001 reviews)
1/04/25
"We like staying here."

Reviewed on Jan 9, 2025

Embassy Suites by Hilton Lexington Green
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
The price is $73 per night from Jan 19 to Jan 20
$73
includes taxes & fees
Jan 19 - Jan 20
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! (1,093 reviews)
"The Guesthouse was very nice. The rooms were large, the beds comfortable, and breakfast was more than sufficient. The price was right too."

Reviewed on Jan 10, 2025

GuestHouse Lexington
21c Museum Hotel Lexington
21c Museum Hotel Lexington
4 out of 5
167 West Main Street, Lexington, KY
The price is $171 per night from Feb 9 to Feb 10
$171
includes taxes & fees
Feb 9 - Feb 10
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! (1,001 reviews)
"Great place to stay. The rooms are clean the art is fun, and the staff is nice and friendly. There are plenty of great food options around the hotel that are walkable. Close to Rupp Arena."

Reviewed on Jan 9, 2025

21c Museum Hotel Lexington
See all 1,090 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.