Cheap Flights To Winchester 2026

Winchester Flights as Low as $117

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Dec 1 - Mon, Dec 7
DCA
Ronald Reagan Washington National
CVG
Cincinnati - Northern Kentucky Intl.
$117
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Dec 1 from Ronald Reagan Washington National to Cincinnati - Northern Kentucky Intl., returning Mon, Dec 7, priced at $117 found 2 days ago
Frontier Airlines
Frontier Airlines
Frontier Airlines
Tue, Dec 1 - Wed, Dec 2
BWI
Baltimore Washington Intl. Thurgood Marshall
CVG
Cincinnati - Northern Kentucky Intl.
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Dec 1 from Baltimore Washington Intl. Thurgood Marshall to Cincinnati - Northern Kentucky Intl., returning Wed, Dec 2, priced at $128 found 2 days ago
Frontier Airlines
Frontier Airlines
Frontier Airlines
United
Fri, Nov 27 - Thu, Dec 3
IAD
Washington Dulles Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$207
Roundtrip
found 2 days ago
Select United flight, departing Fri, Nov 27 from Washington Dulles Intl. to Cincinnati - Northern Kentucky Intl., returning Thu, Dec 3, priced at $207 found 2 days ago
American Airlines
Thu, Nov 26 - Fri, Nov 27
DCA
Ronald Reagan Washington National
CVG
Cincinnati - Northern Kentucky Intl.
$207
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Nov 26 from Ronald Reagan Washington National to Cincinnati - Northern Kentucky Intl., returning Fri, Nov 27, priced at $207 found 2 days ago
Frontier Airlines
Sat, Nov 14 - Wed, Nov 18
EWR
Newark Liberty Intl. Airport
CVG
Cincinnati - Northern Kentucky Intl.
$230
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Newark Liberty Intl. Airport to Cincinnati - Northern Kentucky Intl., returning Wed, Nov 18, priced at $230 found 9 hours ago
Southwest Airlines
Fri, Nov 27 - Tue, Dec 1
BWI
Baltimore Washington Intl. Thurgood Marshall
CVG
Cincinnati - Northern Kentucky Intl.
$265
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Fri, Nov 27 from Baltimore Washington Intl. Thurgood Marshall to Cincinnati - Northern Kentucky Intl., returning Tue, Dec 1, priced at $265 found 11 hours ago
Southwest Airlines
Frontier Airlines
Tue, Oct 27 - Sat, Oct 31
MSY
Louis Armstrong New Orleans Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$290
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Louis Armstrong New Orleans Intl. to Cincinnati - Northern Kentucky Intl., returning Sat, Oct 31, priced at $290 found 5 hours ago
Frontier Airlines
Fri, Nov 13 - Sat, Nov 21
SEA
Seattle - Tacoma Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$335
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, Nov 13 from Seattle - Tacoma Intl. to Cincinnati - Northern Kentucky Intl., returning Sat, Nov 21, priced at $335 found 16 hours ago
Alaska Airlines
Sat, Nov 14 - Tue, Nov 17
SEA
Seattle - Tacoma Intl.
CVG
Cincinnati - Northern Kentucky Intl.
$377
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Sat, Nov 14 from Seattle - Tacoma Intl. to Cincinnati - Northern Kentucky Intl., returning Tue, Nov 17, priced at $377 found 16 hours ago
Southwest Airlines

Flights to Winchester

No matter how much you fight the travel bug, sometimes there's only one solution—to hop on the next plane to Winchester. AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. AARP Travel features their members-only discount with the best rates from Expedia, so members will get the best price in travel, guaranteed.

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Whether it's a ski escape, weekend getaway, tropical destination, backpacking adventure or another trip you're dreaming of–we'll help you get there (without breaking the bank).

Airport Transportation

Once you have got your flight scheduled to Winchester, you might want to book a vehicle so you can get around on your own. You can request Winchester rental cars under our cars tab and jump in the driver's seat as soon as you step outside. If you do not need a rental car, there are other ground transportation options such as shuttle, limousine, taxi, and ride booking app services.

Things to Do in Winchester

If you aren't sure where to start, we can help you with that too. Not to worry—there's plenty to do in this city. No matter what you decide to do with your time, you're sure to have fun in this city.

If you're looking for some fun activities to do in Winchester, make sure you look at our "Things to Do in Winchester" page for excursions and activities for the whole crew.

Where to Stay in Winchester

Winchester has lodging to choose from, make sure you check out our hotel listings tab for some great recommendations from past visitors. Remember that you will get the best price out there when you book your stay with us.

Booking Your Trip to Winchester

We know that you want to focus more on the fun stuff and less on the airfare prices, so we provide travel arrangements that fall within your budget. There is no better time than now to start booking that next trip. Book one of our flights today.