Cheap Flights from White Plains (HPN) to Winchester (WGO)

Popular airlines from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional)

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Frequently asked questions

How much does a flight from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional) cost?
Secure a cheap one-way flight or cheap return flight from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional)?
The cheapest month to fly from HPN to WGO is , when there's less demand. Off-peak months are generally when airlines offer better prices between these airports.
What is the cheapest airline that flies from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional)?
To find the cheapest airline flying from HPN to WGO, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional)?
You'll have to hop on a flight with a layover if you're traveling from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from HPN to WGO?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* However, this can vary depending on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional)?
To arrive at Winchester, VA (WGO-Winchester Regional) on time, pick a flight that leaves Westchester County Airport (HPN) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional) last-minute?
Holding off until just before your trip to book a ticket from HPN to WGO generally means paying more. While you might find some last-minute discounts, there's no guarantee. Keep your travel schedule open for a better chance of scoring a bargain.
Is it cheaper to book a HPN to WGO flight and hotel package?
Compared with arranging flights and hotels separately, booking a HPN to WGO flight and hotel package with Expedia could lead to significant savings. What's more, having it all in one place will take the stress out of planning your trip. Just secure your flights and choose from our extensive range of stays, then customize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Westchester County Airport (HPN) to Winchester, VA (WGO-Winchester Regional)?
If you booked your HPN to WGO flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

Travel information

Travel information

Origin airport
Westchester County
Destination airport
Winchester Regional
Distance
269 mi

Book with confidence

Book with confidence

White Plains to Winchester Flights

The cheapest times to fly from White Plains to Winchester

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from White Plains to Winchester are during the month of . You can find some of the cheapest flights from White Plains to Winchester with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from White Plains to Winchester

Sunday is one of the best days to book for cheap flights from White Plains to Winchester: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from White Plains to Winchester

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from White Plains to Winchester in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap White Plains to Winchester flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your White Plains to Winchester airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

White Plains to Winchester Flights

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