Search Cheap Flights to
Winchester

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Winchester Flights as Low as $159

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

Delta
Sun, Sep 14 - Sun, Sep 21
DCA
Ronald Reagan Washington National
LEX
Blue Grass
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Sep 14 from Ronald Reagan Washington National to Blue Grass, returning Sun, Sep 21, priced at $159 found 1 day ago
American Airlines
Thu, Sep 18 - Sat, Sep 20
IAD
Washington Dulles Intl.
LEX
Blue Grass
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Sep 18 from Washington Dulles Intl. to Blue Grass, returning Sat, Sep 20, priced at $181 found 2 days ago
American Airlines
Wed, Oct 8 - Sat, Oct 18
ORD
O'Hare Intl.
LEX
Blue Grass
$189 Roundtrip, found 8 hours ago
$189
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Oct 8 from O'Hare Intl. to Blue Grass, returning Sat, Oct 18, priced at $189 found 8 hours ago
American Airlines
Sat, Aug 30 - Sun, Aug 31
FLL
Fort Lauderdale - Hollywood Intl.
LEX
Blue Grass
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 30 from Fort Lauderdale - Hollywood Intl. to Blue Grass, returning Sun, Aug 31, priced at $202 found 1 day ago
American Airlines
Tue, Oct 14 - Sat, Oct 18
CLD
McClellan-Palomar
LEX
Blue Grass
$227 Roundtrip, found 5 hours ago
$227
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, Oct 14 from McClellan-Palomar to Blue Grass, returning Sat, Oct 18, priced at $227 found 5 hours ago
American Airlines
Wed, Sep 10 - Wed, Sep 17
BWI
Baltimore Washington Intl. Thurgood Marshall
LEX
Blue Grass
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Sep 10 from Baltimore Washington Intl. Thurgood Marshall to Blue Grass, returning Wed, Sep 17, priced at $229 found 2 hours ago
United
Mon, Aug 25 - Sat, Aug 30
RIC
Richmond Intl.
LEX
Blue Grass
$234 Roundtrip, found 2 hours ago
$234
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Aug 25 from Richmond Intl. to Blue Grass, returning Sat, Aug 30, priced at $234 found 2 hours ago
Bargain Flight
Tue, Aug 19 - Sat, Aug 23
AUS
Austin-Bergstrom Intl.
LEX
Blue Grass
$246 Roundtrip, found 10 hours ago
$246
Roundtrip
found 10 hours ago
Select Bargain Flight flight, departing Tue, Aug 19 from Austin-Bergstrom Intl. to Blue Grass, returning Sat, Aug 23, priced at $246 found 10 hours ago
Delta
Tue, Oct 7 - Tue, Oct 14
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$249 Roundtrip, found 23 hours ago
$249
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Oct 7 from Newark Liberty Intl. Airport to Blue Grass, returning Tue, Oct 14, priced at $249 found 23 hours ago
American Airlines
Sat, Oct 18 - Tue, Oct 21
HOU
William P. Hobby
LEX
Blue Grass
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 18 from William P. Hobby to Blue Grass, returning Tue, Oct 21, priced at $249 just found
Delta
Sat, Oct 18 - Tue, Oct 21
IAH
George Bush Intercontinental
LEX
Blue Grass
$249 Roundtrip, just found
$249
Roundtrip
just found
Select Delta flight, departing Sat, Oct 18 from George Bush Intercontinental to Blue Grass, returning Tue, Oct 21, priced at $249 just found
American Airlines
Fri, Sep 5 - Sat, Sep 6
SAN
San Diego Intl.
LEX
Blue Grass
$258 Roundtrip, found 4 hours ago
$258
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Sep 5 from San Diego Intl. to Blue Grass, returning Sat, Sep 6, priced at $258 found 4 hours ago
Bargain Flight
Sat, Sep 20 - Tue, Sep 30
PHX
Sky Harbor Intl.
LEX
Blue Grass
$260 Roundtrip, found 4 days ago
$260
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Sat, Sep 20 from Sky Harbor Intl. to Blue Grass, returning Tue, Sep 30, priced at $260 found 4 days ago
American Airlines
Tue, Aug 12 - Sat, Aug 16
BOS
Logan Intl.
LEX
Blue Grass
$262 Roundtrip, found 13 hours ago
$262
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Aug 12 from Logan Intl. to Blue Grass, returning Sat, Aug 16, priced at $262 found 13 hours ago
Delta
Tue, Sep 16 - Tue, Sep 23
ATL
Hartsfield-Jackson Atlanta Intl.
LEX
Blue Grass
$270 Roundtrip, found 14 hours ago
$270
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Sep 16 from Hartsfield-Jackson Atlanta Intl. to Blue Grass, returning Tue, Sep 23, priced at $270 found 14 hours ago
Delta
Wed, Sep 3 - Tue, Sep 23
MFR
Rogue Valley Intl.
LEX
Blue Grass
$362 Roundtrip, found 16 hours ago
$362
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Sep 3 from Rogue Valley Intl. to Blue Grass, returning Tue, Sep 23, priced at $362 found 16 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 September, 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 14 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 $159, 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 $159 right now, why wait?

Winchester Flight Information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Roundtrip price
$159

Last Minute Hotel Deals in Winchester

Value Stay

Value Stay

2 out of 5
5100 Revilo Rd, Winchester, KY
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Community Park and Wiseman Park are located ...
8/10 Very Good! (87 reviews)
"Nice clean place"

Reviewed on Jul 13, 2025

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Value Stay
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
7/10 Good! (733 reviews)
"The staff was exceptionally friendly and the hotel, room and pool were very clean. But, the bed that we had was hard and pillows were lumpy and very uncomfortable."

Reviewed on Jul 28, 2025

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Baymont by Wyndham Winchester
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
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! (1,647 reviews)
"Very clean and comfortable. Perfect for our stay en route to our vacation destination."

Reviewed on Aug 2, 2025

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Quality Inn Lexington -Horse Park
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd, Lexington, KY
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 ...
8.4/10 Very Good! (109 reviews)
"This is a little different than most hotels but we like this new style."

Reviewed on Aug 5, 2025

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Spark by Hilton Lexington Hamburg
The Manchester

The Manchester

4 out of 5
941 Manchester St, Lexington, KY
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! (944 reviews)
"We loved the trendy vibe of the hotel — everything felt stylish but still cozy. We ended up eating most of our meals right at the hotel and honestly, the food didn’t disappoint. Service was consistently great, our bed was super comfortable, and the whole place was spotless. Would definitely recommend ..."

Reviewed on Jul 29, 2025

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The Manchester
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
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 ...
8.2/10 Very Good! (1,300 reviews)
"Check in was quick and easy"

Reviewed on Aug 4, 2025

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GuestHouse 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
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! (495 reviews)
"It is a great place, we stay here a lot love everything about this hotel."

Reviewed on Jul 28, 2025

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Marriott Lexington Griffin Gate Golf Resort & Spa
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

3 out of 5
2100 Hackney Pl, Lexington, KY
Stay at this 3-star business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,001 reviews)
"We were passing through, so a very convenient place to stop. Friendly staff."

Reviewed on Aug 5, 2025

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Fairfield Inn & Suites by Marriott Lexington North
See all 1,146 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.