Cheap Flights To Winchester 2026

Winchester Flights as Low as $188

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.

Frontier Airlines
Tue, Nov 10 - Sat, Nov 14
MSP
Minneapolis - St. Paul Intl.
DCA
Ronald Reagan Washington National
$188
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Nov 10 from Minneapolis - St. Paul Intl. to Ronald Reagan Washington National, returning Sat, Nov 14, priced at $188 found 2 days ago
Frontier Airlines
Thu, Nov 5 - Thu, Nov 12
MSP
Minneapolis - St. Paul Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$188
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Nov 5 from Minneapolis - St. Paul Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Nov 12, priced at $188 found 2 days ago
Frontier Airlines
Frontier Airlines
United
Sun Country Airlines
Delta
Sat, Sep 5 - Mon, Sep 14
BDL
Bradley Intl.
DCA
Ronald Reagan Washington National
$238
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Sep 5 from Bradley Intl. to Ronald Reagan Washington National, returning Mon, Sep 14, priced at $238 found 22 hours ago
Frontier Airlines
Frontier Airlines
Frontier Airlines
Fri, Aug 21 - Thu, Aug 27
PHX
Sky Harbor Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$275
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Aug 21 from Sky Harbor Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Aug 27, priced at $275 found 4 days ago
JetBlue Airways
Delta
Tue, Oct 20 - Tue, Oct 27
DAB
Daytona Beach Intl.
IAD
Washington Dulles Intl.
$343
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Daytona Beach Intl. to Washington Dulles Intl., returning Tue, Oct 27, priced at $343 found 1 day ago
Delta
Tue, Oct 20 - Tue, Oct 27
DAB
Daytona Beach Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$357
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Daytona Beach Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 27, priced at $357 found 1 day ago
TAP Portugal
British Airways
United
Thu, Sep 17 - Sun, Sep 20
BCN
Barcelona Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$742
Roundtrip
found 1 day ago
Select United flight, departing Thu, Sep 17 from Barcelona Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 20, priced at $742 found 1 day ago

Flights to

If is calling your name, then book your next flight to (airport). And with the AARP Travel Center Powered by Expedia®, this trip isn't too far out of reach. With the best rates from Expedia combined with members-only discounts, AARP Travel offers members the best price in travel, guaranteed.

AARP members get exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

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

Transportation at the Airport

Once you have reserved plane tickets to , you may want to book a car so you can get around on your own. You can request car rentals under our cars tab and hop into the driver's seat as soon as you step outside. For more information, check out the Winchester (and vicinity) Car Rentals Guide.

Things to Do in

Not sure where to start? 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 , make sure you look at our "Things to Do in Winchester (and vicinity)" page for excursions and activities for the whole clan.

Book Your Hotel in

has hotel to choose from, make sure you check out our hotel listings tab for some great recommendations from past visitors. No matter where you stay, just remember that you'll get the best price out there when you stay with AARP Travel.

Booking Your Flight

Once you have planned your travel dates, allow us here at AARP Travel to connect you with inexpensive tickets to . Do not wait a moment longer—book your airfare today and land in tomorrow.