$41 Cheap Flights to New Windsor, NY

Popular airlines to New Windsor

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 $82 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Breeze Airways
JetBlue Airways
American Airlines
Delta

Tips to find the cheapest flights to New Windsor

The cheapest day to fly

Get started finding a cheap flight to New Windsor on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

September is the cheapest month to fly to New Windsor. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to New Windsor. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to New Windsor, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to New Windsor

The lowest price for round-trip flights to New Windsor in 2025 starts from from $82, while one-way tickets start from from $41. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to New Windsor. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to New Windsor

Breeze Airways, American Airlines, JetBlue Airways, Delta are just some of the airlines that can typically offer cheap tickets to New Windsor. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to New Windsor and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for New Windsor, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to New Windsor. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your New Windsor plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to New Windsor

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to New Windsor.

Stopover savings

The cheapest tickets to New Windsor are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to New Windsor. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to New Windsor for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to New Windsor. Simply download the free Expedia app to your smart device and activate New Windsor flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to New Windsor. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

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

Frequently asked questions

What month is the cheapest to fly to New Windsor?
July is usually the cheapest month for flights to New Windsor*. Be sure to check for cheap flights during this time as you may be able to snag a good deal. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
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.
Flights to New Windsor information
Destination airport
Westchester County
Destination airport IATA code
HPN
Destination city name
White Plains
Roundtrip price
$81

Trending flights to New Windsor

Prices were available within the past 7 days and start at $41 for one-way flights and $82 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways

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*Available to One Key members.