Search Cheap Flights to
Winchester

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Winchester Flights as Low as $220

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

Delta
Sat, May 10 - Mon, May 12
CLE
Hopkins Intl.
LEX
Blue Grass
$220 Roundtrip, found 6 days ago
$220
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, May 10 from Hopkins Intl. to Blue Grass, returning Mon, May 12, priced at $220 found 6 days ago
Delta
Mon, May 5 - Mon, May 12
CLE
Hopkins Intl.
LEX
Blue Grass
$220 Roundtrip, found 6 days ago
$220
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, May 5 from Hopkins Intl. to Blue Grass, returning Mon, May 12, priced at $220 found 6 days ago
American Airlines
Wed, May 7 - Sat, May 10
CLE
Hopkins Intl.
LEX
Blue Grass
$222 Roundtrip, found 17 hours ago
$222
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, May 7 from Hopkins Intl. to Blue Grass, returning Sat, May 10, priced at $222 found 17 hours ago
American Airlines
Fri, Jul 4 - Tue, Jul 8
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 4 from Newark Liberty Intl. Airport to Blue Grass, returning Tue, Jul 8, priced at $224 found 1 day ago
American Airlines
Fri, Jul 4 - Sat, Jul 5
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$229 Roundtrip, found 6 days ago
$229
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jul 4 from Newark Liberty Intl. Airport to Blue Grass, returning Sat, Jul 5, priced at $229 found 6 days ago
Delta
Fri, Jul 4 - Tue, Jul 8
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 4 from Newark Liberty Intl. Airport to Blue Grass, returning Tue, Jul 8, priced at $233 found 1 day ago
United
Mon, May 5 - Sat, May 10
CLE
Hopkins Intl.
LEX
Blue Grass
$233 Roundtrip, found 6 days ago
$233
Roundtrip
found 6 days ago
Select United flight, departing Mon, May 5 from Hopkins Intl. to Blue Grass, returning Sat, May 10, priced at $233 found 6 days ago
United
Fri, Jul 4 - Sat, Jul 5
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$235 Roundtrip, found 6 days ago
$235
Roundtrip
found 6 days ago
Select United flight, departing Fri, Jul 4 from Newark Liberty Intl. Airport to Blue Grass, returning Sat, Jul 5, priced at $235 found 6 days ago
United
Mon, May 5 - Sat, May 10
CLE
Hopkins Intl.
LEX
Blue Grass
$238 Roundtrip, found 6 days ago
$238
Roundtrip
found 6 days ago
Select United flight, departing Mon, May 5 from Hopkins Intl. to Blue Grass, returning Sat, May 10, priced at $238 found 6 days ago
Delta
Mon, May 5 - Sat, May 10
CLE
Hopkins Intl.
LEX
Blue Grass
$241 Roundtrip, found 6 days ago
$241
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, May 5 from Hopkins Intl. to Blue Grass, returning Sat, May 10, priced at $241 found 6 days ago
Delta
Sat, May 17 - Tue, May 20
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, May 17 from Newark Liberty Intl. Airport to Blue Grass, returning Tue, May 20, priced at $251 found 3 days ago
American Airlines
Fri, Jul 4 - Tue, Jul 8
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$252 Roundtrip, found 1 day ago
$252
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 4 from Newark Liberty Intl. Airport to Blue Grass, returning Tue, Jul 8, priced at $252 found 1 day ago
Delta
Sat, May 17 - Mon, May 19
EWR
Newark Liberty Intl. Airport
LEX
Blue Grass
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, May 17 from Newark Liberty Intl. Airport to Blue Grass, returning Mon, May 19, priced at $256 found 3 days ago
American Airlines
Tue, Aug 19 - Sun, Aug 24
YVR
Vancouver Intl.
LEX
Blue Grass
$371 Roundtrip, found 23 hours ago
$371
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Tue, Aug 19 from Vancouver Intl. to Blue Grass, returning Sun, Aug 24, priced at $371 found 23 hours ago
WestJet
Mon, Aug 18 - Thu, Aug 28
YVR
Vancouver Intl.
LEX
Blue Grass
$428 Roundtrip, found 23 hours ago
$428
Roundtrip
found 23 hours ago
Select WestJet flight, departing Mon, Aug 18 from Vancouver Intl. to Blue Grass, returning Thu, Aug 28, priced at $428 found 23 hours ago
Delta
Thu, May 8 - Sun, May 11
BDL
Bradley Intl.
LEX
Blue Grass
$588 Roundtrip, found 1 day ago
$588
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, May 8 from Bradley Intl. to Blue Grass, returning Sun, May 11, priced at $588 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 May, 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 $220, 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 $220 right now, why wait?

Winchester Flight Information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Roundtrip price
$219

Last Minute Hotel Deals in Winchester

Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
The price is $88 per night from Apr 22 to Apr 23
$88
includes taxes & fees
Apr 22 - Apr 23
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! (660 reviews)
"I booked for the pool and the heater was not working so it was too cold to use comfortably"

Reviewed on Apr 10, 2025

Baymont by Wyndham Winchester
The Manchester
The Manchester
4 out of 5
941 Manchester St, Lexington, KY
The price is $244 per night from May 4 to May 5
$244
includes taxes & fees
May 4 - May 5
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! (782 reviews)
Clean, Convenient, and Friendly!
"⸻ I had a wonderful stay at this Manchester hotel! The location was perfect—close to everything I needed, with great access to public transportation and local attractions. The staff were incredibly friendly and welcoming, always ready to help with a smile. The room was clean, well-appointed, and ..."

Reviewed on Apr 7, 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 $82 per night from Apr 29 to Apr 30
$82
includes taxes & fees
Apr 29 - Apr 30
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! (1,523 reviews)
"Good shower, great breakfast, however, quit serving at 9:30 when most hotels we'd stayed at stopped at 10 AM."

Reviewed on Apr 11, 2025

Quality Inn Lexington -Horse Park
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5
2261 Elkhorn Road, Lexington, KY
The price is $71 per night from Apr 28 to Apr 29
$71
includes taxes & fees
Apr 28 - Apr 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 ...
8.2/10 Very Good! (1,161 reviews)
Roadtrip
"The desk clerk was so helpful. Room was very nice, clean etc. No elevators. 2 story. Location convenient. Would recommend"

Reviewed on Apr 8, 2025

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
The price is $131 per night from Apr 20 to Apr 21
$131
includes taxes & fees
Apr 20 - Apr 21
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! (404 reviews)
"Excellent stay !"

Reviewed on Apr 8, 2025

Marriott Lexington Griffin Gate Golf Resort & Spa
GLō Best Western Lexington
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
The price is $113 per night from Apr 20 to Apr 21
$113
includes taxes & fees
Apr 20 - Apr 21
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! (2,288 reviews)
N
"The hotel was cute and clean. Breakfast was the usual, but okay. Biggest problem was the person who checked into their room over top of ours at midnight, and then proceeded to STOMP back and forth across the floor every few minutes until 2:30 a.m. Really messed with our sleep. What is wrong with ..."

Reviewed on Apr 10, 2025

GLō Best Western 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
The price is $117 per night from Apr 20 to Apr 21
$117
includes taxes & fees
Apr 20 - Apr 21
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! (1,003 reviews)
Will stay again when in Lexington
"Great breakfast with personal omelets; very inviting eating area; rooms were clean and comfy beds; we were able to get ajoining rooms for grandchildren;"

Reviewed on Apr 8, 2025

Embassy Suites by Hilton Lexington/UK Coldstream
Everhome Suites Lexington - Horse Park
Everhome Suites Lexington - Horse Park
2.5 out of 5
757 Newtown Springs Drive, Lexington, KY
The price is $107 per night from Apr 14 to Apr 15
$107
includes taxes & fees
Apr 14 - Apr 15
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (165 reviews)
"Great"

Reviewed on Apr 11, 2025

Everhome Suites Lexington - Horse Park
See all 1,100 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.