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 $229

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

Delta
Wed, Mar 12 - Mon, Mar 17
BWI
Baltimore Washington Intl. Thurgood Marshall
LEX
Blue Grass
$229 Roundtrip, found 4 days ago
$229
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Mar 12 from Baltimore Washington Intl. Thurgood Marshall to Blue Grass, returning Mon, Mar 17, priced at $229 found 4 days ago
American Airlines
Tue, Apr 22 - Sat, Apr 26
BWI
Baltimore Washington Intl. Thurgood Marshall
LEX
Blue Grass
$229 Roundtrip, found 3 hours ago
$229
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Apr 22 from Baltimore Washington Intl. Thurgood Marshall to Blue Grass, returning Sat, Apr 26, priced at $229 found 3 hours ago
Delta
Sat, Jun 7 - Wed, Jun 11
RDU
Raleigh - Durham Intl.
LEX
Blue Grass
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 7 from Raleigh - Durham Intl. to Blue Grass, returning Wed, Jun 11, priced at $230 found 1 day ago
Delta
Tue, Mar 4 - Tue, Mar 11
PNS
Pensacola Intl.
LEX
Blue Grass
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 4 from Pensacola Intl. to Blue Grass, returning Tue, Mar 11, priced at $249 found 1 day ago
United
Tue, Mar 18 - Wed, Mar 19
LGA
LaGuardia
LEX
Blue Grass
$257 Roundtrip, found 3 hours ago
$257
Roundtrip
found 3 hours ago
Select United flight, departing Tue, Mar 18 from LaGuardia to Blue Grass, returning Wed, Mar 19, priced at $257 found 3 hours ago
Delta
Mon, Mar 10 - Sun, Mar 16
SEA
Seattle - Tacoma Intl.
LEX
Blue Grass
$290 Roundtrip, found 3 hours ago
$290
Roundtrip
found 3 hours ago
Select Delta flight, departing Mon, Mar 10 from Seattle - Tacoma Intl. to Blue Grass, returning Sun, Mar 16, priced at $290 found 3 hours ago
Delta
Tue, Apr 29 - Tue, May 6
DCA
Ronald Reagan Washington National
LEX
Blue Grass
$301 Roundtrip, found 5 days ago
$301
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Apr 29 from Ronald Reagan Washington National to Blue Grass, returning Tue, May 6, priced at $301 found 5 days ago
American Airlines
Tue, Feb 18 - Tue, Feb 25
COS
Colorado Springs
LEX
Blue Grass
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 18 from Colorado Springs to Blue Grass, returning Tue, Feb 25, priced at $324 found 1 day ago
American Airlines
Tue, Mar 25 - Tue, Apr 1
SLC
Salt Lake City Intl.
LEX
Blue Grass
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 25 from Salt Lake City Intl. to Blue Grass, returning Tue, Apr 1, priced at $349 found 1 day ago
WestJet
Tue, Mar 25 - Tue, Apr 1
YYC
Calgary Intl.
LEX
Blue Grass
$376 Roundtrip, found 1 day ago
$376
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, Mar 25 from Calgary Intl. to Blue Grass, returning Tue, Apr 1, priced at $376 found 1 day ago
Delta
Wed, Feb 12 - Sat, Feb 15
PHL
Philadelphia Intl.
LEX
Blue Grass
$454 Roundtrip, found 11 hours ago
$454
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Feb 12 from Philadelphia Intl. to Blue Grass, returning Sat, Feb 15, priced at $454 found 11 hours ago
Delta
Tue, Mar 25 - Tue, Apr 1
PIH
Pocatello Regional
LEX
Blue Grass
$561 Roundtrip, found 1 day ago
$561
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 25 from Pocatello Regional to Blue Grass, returning Tue, Apr 1, priced at $561 found 1 day ago
Delta
Fri, May 16 - Tue, May 20
EUG
Eugene
LEX
Blue Grass
$586 Roundtrip, found 1 day ago
$586
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 16 from Eugene to Blue Grass, returning Tue, May 20, priced at $586 found 1 day ago
Alaska Airlines
Mon, Mar 10 - Thu, Mar 20
SEA
Seattle - Tacoma Intl.
LEX
Blue Grass
$592 Roundtrip, found 3 hours ago
$592
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Mon, Mar 10 from Seattle - Tacoma Intl. to Blue Grass, returning Thu, Mar 20, priced at $592 found 3 hours ago
American Airlines
Sat, Mar 29 - Tue, Apr 1
IDA
Idaho Falls Regional
LEX
Blue Grass
$642 Roundtrip, found 1 day ago
$642
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Mar 29 from Idaho Falls Regional to Blue Grass, returning Tue, Apr 1, priced at $642 found 1 day ago
Air Canada
Wed, Mar 26 - Mon, Mar 31
YYC
Calgary Intl.
LEX
Blue Grass
$869 Roundtrip, found 1 day ago
$869
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Mar 26 from Calgary Intl. to Blue Grass, returning Mon, Mar 31, priced at $869 found 1 day 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 March, 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
$228

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 $104 per night from Feb 18 to Feb 19
$104
includes taxes & fees
Feb 18 - Feb 19
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! (2,281 reviews)
"This property was quiet, nicely decorated and very convenient. We would choose this facility again."

Reviewed on Feb 9, 2025

GLō Best Western Lexington
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
The price is $161 per night from Feb 23 to Feb 24
$161
includes taxes & fees
Feb 23 - Feb 24
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! (1,005 reviews)
"The hotel is nice and clean. Prof"

Reviewed on Feb 9, 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 $108 per night from Feb 18 to Feb 19
$108
includes taxes & fees
Feb 18 - Feb 19
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! (1,005 reviews)
"Everything"

Reviewed on Feb 10, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
The price is $246 per night from Feb 23 to Feb 24
$246
includes taxes & fees
Feb 23 - Feb 24
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! (696 reviews)
Surprisingly fantastic
"Absolutely phenomenal. Most surprising was the food in the downstairs restaurant. It’s a mix of Ecuadorian and Southern flare, the food is absolutely delicious!"

Reviewed on Feb 8, 2025

The Manchester
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 $73 per night from Mar 3 to Mar 4
$73
includes taxes & fees
Mar 3 - Mar 4
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! (1,418 reviews)
"Legit place to relax and let loose for those in travel"

Reviewed on Feb 10, 2025

Quality Inn Lexington -Horse Park
Hyatt Regency Lexington
Hyatt Regency Lexington
3.5 out of 5
401 W High St, Lexington, KY
The price is $147 per night from Feb 23 to Feb 24
$147
includes taxes & fees
Feb 23 - Feb 24
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! (1,003 reviews)
"Thankful they were able to switch our room. When we got there our room was 95. Maintenance came and found the problem. They couldn’t fix immediately so they got us another room and 2 vouchers for the blue fire grill breakfast. Very nice of them to do it."

Reviewed on Feb 7, 2025

Hyatt Regency Lexington
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 $127 per night from Feb 23 to Feb 24
$127
includes taxes & fees
Feb 23 - Feb 24
Stay at this 4.5-star luxury resort in Lexington. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (364 reviews)
Nice stay
"We were impressed by the hotel lobby ; very cool ambiance that really let's you know you're in Bourbon country. Room was nice and clean. The bed was very firm and the solitary blanket was thin for January; would have been nice to have a blanket in the room or a thicker duvet for such a nice hotel. ..."

Reviewed on Jan 31, 2025

Marriott Lexington Griffin Gate Golf Resort & Spa
Elwood Hotel & Suites
Elwood Hotel & Suites
4 out of 5
444 Parkway Drive, Lexington, KY
The price is $127 per night from Feb 16 to Feb 17
$127
includes taxes & fees
Feb 16 - Feb 17
Stay at this 4-star hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our ...
9.2/10 Wonderful! (917 reviews)
"Great place!"

Reviewed on Feb 7, 2025

Elwood Hotel & Suites
See all 1,098 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.