Cheap Flights from New York (JFK) to Winchester (WGO)

Popular airlines from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional)

Frequently asked questions

How much does a flight from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional) cost?
Grab a cheap one-way flight or cheap return flight from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional)?
Flying in is a great way to save, as it's the cheapest month for flights between JFK and WGO. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest JFK to WGO flight.
How many flights per day from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional)?
You'll need to catch a flight with a layover when traveling from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional). There are no daily direct flights on this route. However, just filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from JFK to WGO?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional)?
To land at Winchester, VA (WGO-Winchester Regional) without delays, choose a flight that takes off from John F. Kennedy Intl. Airport (JFK) 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.
What airports do you fly into for Winchester from John F. Kennedy Intl. Airport (JFK)?
If you're taking a direct flight from John F. Kennedy Intl. Airport (JFK) to Winchester, Washington Dulles Intl. Airport (IAD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional) last-minute?
Last-minute bookings from JFK to WGO are generally more expensive. To lock in the best rates, start looking for flights well in advance. That being said, if your travel plans are flexible, you may score a cheap fare just before your departure.
Is it cheaper to book a JFK to WGO flight and hotel package?
Opting for a JFK to WGO flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Pick from our wide range of accommodations and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from John F. Kennedy Intl. Airport (JFK) to Winchester, VA (WGO-Winchester Regional)?
Usually, it's possible to reschedule or cancel your JFK to WGO flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
John F. Kennedy Intl.
Destination airport
Winchester Regional
Distance
253 mi

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New York to Winchester Flights

The cheapest times to fly from New York 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 New York to Winchester are during the month of . You can find some of the cheapest flights from New York to Winchester with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from New York to Winchester

Sunday is one of the best days to book for cheap flights from New York 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 New York 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 New York 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 New York 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 New York 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.

 

New York to Winchester Flights

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*Available to One Key members.