$41 Cheap Flights to New Windsor, NY

View $41 flight on Wed, Aug 26, 2026Opens in a new window

Popular airlines to New Windsor

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How much is the cheapest flight to New Windsor?

Prices were available within the past 7 days and start at $41 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Fri, Sep 25 - Tue, Sep 29
RDU
Raleigh
HPN
White Plains
$97 Roundtrip, found 3 hours ago
$97
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Sep 25 from Raleigh to White Plains, returning Tue, Sep 29, priced at $97 found 3 hours ago
Breeze Airways
Fri, Sep 11 - Mon, Sep 14
RDU
Raleigh
HPN
White Plains
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh to White Plains, returning Mon, Sep 14, priced at $102 found 5 hours ago
Breeze Airways
Sat, Sep 26 - Tue, Sep 29
RDU
Raleigh
HPN
White Plains
$107 Roundtrip, found 13 hours ago
$107
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Sat, Sep 26 from Raleigh to White Plains, returning Tue, Sep 29, priced at $107 found 13 hours ago
American Airlines
Tue, Aug 18 - Fri, Aug 21
MCO
Orlando
HPN
White Plains
$141 Roundtrip, found 2 days ago
$141
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 18 from Orlando to White Plains, returning Fri, Aug 21, priced at $141 found 2 days ago
Delta
Wed, Apr 29 - Tue, May 19
MCO
Orlando
HPN
White Plains
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 29 from Orlando to White Plains, returning Tue, May 19, priced at $197 found 2 days ago

Alternative airports near New Windsor

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Westchester County HPN. Cheapest option available. Average driving time to city center is 1 hour 5 minutes. Flights from $331
HPN
Westchester County
Cheapest
Average driving time to city center1 h 5 min
Flights from $331

Frequently asked questions

What month is the cheapest to fly to New Windsor?
The cheapest month to fly to New Windsor is September when there's less demand. Off-peak months are usually when you'll find cheap flights. To keep costs down, avoid flying during school breaks and public holidays.
Which US cities have the cheapest flights to New Windsor?
Generally, Orlando, Atlanta and Chicago offer cheap flights to New Windsor. However, being flexible is always key to bagging the lowest fares. Head off during low season or midweek to keep costs down.
Which US cities fly direct to New Windsor?
Take your pick of 75 US destinations with direct flights to New Windsor. When you book on Expedia, check "Direct flights only" to compare nonstop routes. Fly to New Windsor from any of these leading cities:

  • Orlando
  • Atlanta
  • Chicago
  • Los Angeles
  • Fort Lauderdale

How to find a cheap flight to New Windsor?
To lock in cheap flights to New Windsor, book well in advance and travel during the off-peak months of January and February. Like another tip? Depart on a Thursday and save 16% on average compared to those who travel on a Sunday.* Opt to receive price alerts on the Expedia app and we'll get in touch as soon as your fares go down.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to New Windsor?
While booking in advance is usually the easiest way to save money, don't panic if your New Windsor getaway is last minute. You can still find cheap flights to New Windsor, especially if your plans have a little wiggle room. Try changing your dates, looking at different ticket options or jetting out of an alternative airport.
How far in advance should I book a flight to New Windsor?
To pick up some of the biggest savings on domestic journeys, book your flight to New Windsor 28 days ahead of your travel dates. For international flights, search for your ticket between two and four months in advance. This increases your chances of securing the departure dates and seats you want.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to New Windsor?
Sundays are generally the best day to book a cheap flight to New Windsor, with savings of around 8% on average compared to Fridays. If you choose to purchase tickets on a Friday, expect to spend more as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to New Windsor?
New Windsor is connected to 168 airports worldwide through 72 airlines, with John F. Kennedy Intl. Airport (JFK) as its chief gateway. Choose from these popular airlines to New Windsor when booking your trip:

  • Delta Air Lines
  • JetBlue Airways
  • American Airlines
  • British Airways

Where do you fly into New Windsor?
When flying to New Windsor, the main airport to touch down at is Stewart Intl. Airport (SWF). You can also jet into nearby hubs like Westchester County Airport (HPN), LaGuardia Airport (LGA) or Liberty Intl. Airport (EWR). An additional option worth keeping in mind when you fly to New Windsor is John F. Kennedy Intl. Airport (JFK).
How far is the airport from central New Windsor?
You'll be about 4 mi northwest of central New Windsor after arriving at Stewart Intl. Airport (SWF).
Can I save money by booking a New Windsor trip package?
You could potentially save hundreds of dollars if you secure a New Windsor flight and hotel package deal on Expedia. And you'll save time and hassle by having all your travel arrangements in one place. Try bundling hotels and flights with extras such as tours and activities for your own personalized New Windsor getaway.
Can I change or cancel my flight to New Windsor?
You can typically change or cancel your flight to New Windsor within 24 hours of booking. However, be mindful that some fares are non-refundable. In those cases, you may receive credit for future flights rather than a direct refund. It's important to check the airline's rules and restrictions in your itinerary for specific details. You can use Expedia's "Changes included" or "No cancel fee" filters when you search to find cheap flights to New Windsor with flexible change policies. For additional information, visit our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
Westchester County
Destination airport IATA code
HPN
Destination city name
White Plains
Roundtrip price
$96

Trending flights to New Windsor

Prices were available within the past 7 days and start at $41 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Fri, Sep 25 - Tue, Sep 29
RDU
Raleigh
HPN
White Plains
$97 Roundtrip, found 3 hours ago
$97
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Sep 25 from Raleigh to White Plains, returning Tue, Sep 29, priced at $97 found 3 hours ago

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