Search Cheap Flights to
Winchester

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Winchester Flights as Low as $162

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

Delta
Tue, Aug 12 - Sun, Aug 17
DCA
Ronald Reagan Washington National
LEX
Blue Grass
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 12 from Ronald Reagan Washington National to Blue Grass, returning Sun, Aug 17, priced at $162 found 1 day ago
Bargain Flight
Sat, Aug 9 - Sat, Aug 16
MKE
General Mitchell Intl.
LEX
Blue Grass
$180 Roundtrip, just found
$180
Roundtrip
just found
Select Bargain Flight flight, departing Sat, Aug 9 from General Mitchell Intl. to Blue Grass, returning Sat, Aug 16, priced at $180 just found
American Airlines
Wed, Oct 8 - Sat, Oct 18
ORD
O'Hare Intl.
LEX
Blue Grass
$189 Roundtrip, just found
$189
Roundtrip
just found
Select American Airlines flight, departing Wed, Oct 8 from O'Hare Intl. to Blue Grass, returning Sat, Oct 18, priced at $189 just found
American Airlines
Sat, Aug 23 - Wed, Aug 27
MSY
Louis Armstrong New Orleans Intl.
LEX
Blue Grass
$193 Roundtrip, just found
$193
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 23 from Louis Armstrong New Orleans Intl. to Blue Grass, returning Wed, Aug 27, priced at $193 just found
Delta
Sat, Aug 30 - Sun, Aug 31
FLL
Fort Lauderdale - Hollywood Intl.
LEX
Blue Grass
$201 Roundtrip, found 3 hours ago
$201
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Aug 30 from Fort Lauderdale - Hollywood Intl. to Blue Grass, returning Sun, Aug 31, priced at $201 found 3 hours ago
Delta
Mon, Jul 28 - Thu, Aug 7
LGA
LaGuardia
LEX
Blue Grass
$213 Roundtrip, found 4 days ago
$213
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Jul 28 from LaGuardia to Blue Grass, returning Thu, Aug 7, priced at $213 found 4 days ago
United
Mon, Aug 25 - Sat, Aug 30
RIC
Richmond Intl.
LEX
Blue Grass
$229 Roundtrip, found 2 hours ago
$229
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Aug 25 from Richmond Intl. to Blue Grass, returning Sat, Aug 30, priced at $229 found 2 hours ago
Bargain Flight
Sun, Aug 31 - Sat, Sep 6
JAX
Jacksonville Intl.
LEX
Blue Grass
$236 Roundtrip, found 3 hours ago
$236
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Sun, Aug 31 from Jacksonville Intl. to Blue Grass, returning Sat, Sep 6, priced at $236 found 3 hours ago
United
Tue, Sep 23 - Wed, Oct 1
RDU
Raleigh - Durham Intl.
LEX
Blue Grass
$249 Roundtrip, found 8 hours ago
$249
Roundtrip
found 8 hours ago
Select United flight, departing Tue, Sep 23 from Raleigh - Durham Intl. to Blue Grass, returning Wed, Oct 1, priced at $249 found 8 hours ago
American Airlines
Wed, Oct 15 - Wed, Oct 22
IAH
George Bush Intercontinental
LEX
Blue Grass
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Wed, Oct 15 from George Bush Intercontinental to Blue Grass, returning Wed, Oct 22, priced at $249 just found
American Airlines
Wed, Sep 24 - Tue, Oct 7
PBI
Palm Beach Intl.
LEX
Blue Grass
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Wed, Sep 24 from Palm Beach Intl. to Blue Grass, returning Tue, Oct 7, priced at $249 just found
Bargain Flight
Tue, Aug 26 - Wed, Sep 3
DFW
Dallas-Fort Worth Intl.
LEX
Blue Grass
$270 Roundtrip, found 3 hours ago
$270
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Tue, Aug 26 from Dallas-Fort Worth Intl. to Blue Grass, returning Wed, Sep 3, priced at $270 found 3 hours ago
United
Sat, Jul 26 - Tue, Jul 29
MSP
Minneapolis - St. Paul Intl.
LEX
Blue Grass
$276 Roundtrip, found 1 day ago
$276
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jul 26 from Minneapolis - St. Paul Intl. to Blue Grass, returning Tue, Jul 29, priced at $276 found 1 day ago
American Airlines
Thu, Oct 23 - Mon, Oct 27
GEG
Spokane Intl.
LEX
Blue Grass
$289 Roundtrip, found 2 hours ago
$289
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Oct 23 from Spokane Intl. to Blue Grass, returning Mon, Oct 27, priced at $289 found 2 hours ago
Delta
Thu, Aug 7 - Tue, Aug 12
SNA
John Wayne
LEX
Blue Grass
$293 Roundtrip, found 1 hour ago
$293
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Aug 7 from John Wayne to Blue Grass, returning Tue, Aug 12, priced at $293 found 1 hour ago
American Airlines
Fri, Aug 29 - Tue, Sep 2
LAX
Los Angeles Intl.
LEX
Blue Grass
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 29 from Los Angeles Intl. to Blue Grass, returning Tue, Sep 2, priced at $294 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 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 13 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 $162, 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 $162 right now, why wait?

Winchester Flight Information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Roundtrip price
$162

Last Minute Hotel Deals in Winchester

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! (718 reviews)
"Quick stay after delayed flight. It had what we needed. Free breakfast that we were not expecting"

Reviewed on Jul 4, 2025

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Baymont by Wyndham Winchester
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 ...
8.8/10 Excellent! (49 reviews)
Great stay, will be back again
"Nice property, and well cared for. The breakfast offerings may have included a better fruit selection before I came down. That would be the only improvement I would suggest."

Reviewed on Jul 10, 2025

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Spark by Hilton Lexington Hamburg
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! (1,629 reviews)
"Great to just get rest to hop back on the road."

Reviewed on Jul 8, 2025

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Quality Inn Lexington -Horse Park
Elwood Hotel & Suites
Elwood Hotel & Suites
4 out of 5
444 Parkway Drive, Lexington, KY
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! (1,000 reviews)
"The breakfast was fantastic, murals everywhere and overall quiet"

Reviewed on Jul 8, 2025

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Elwood Hotel & Suites
Hilton Lexington/Downtown
Hilton Lexington/Downtown
3.5 out of 5
369 West Vine Street, Lexington, KY
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 ...
8.4/10 Very Good! (1,004 reviews)
"Great"

Reviewed on Jul 7, 2025

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Hilton Lexington/Downtown
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 ...
8.6/10 Excellent! (1,003 reviews)
"Comfortable rooms and clean bathrooms. Complimentary breakfast and coffee was great. Parking space was good as well."

Reviewed on Jul 8, 2025

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Fairfield Inn & Suites by Marriott Lexington North
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 ...
8/10 Very Good! (1,241 reviews)
"We had a wonderful stay at your hotel ! Friendly staff , clean rooms and great amenities .. we will definitely be back ...."

Reviewed on Jul 5, 2025

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GuestHouse Lexington
Embassy Suites by Hilton Lexington/UK Coldstream
Embassy Suites by Hilton Lexington/UK Coldstream
3.5 out of 5
1801 Newtown Pike, Lexington, KY
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 ...
8.6/10 Excellent! (1,016 reviews)
Needs some upkeep. Pet friendly&good breakfast.
"We have stayed here numerous times over the years. The hotel is in need of some upkeep. We did appreciate the made to order breakfast and the pet friendly environment. Unfortunately they do charge for parking along with our visitors that came one evening and had to pay $20 just to visit us and have ..."

Reviewed on Jul 7, 2025

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Embassy Suites by Hilton Lexington/UK Coldstream
See all 1,133 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.