Cheap flights To New Windsor (NYC) from $41

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Cheap Flights to New Windsor from $41 One Way, $82 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Jan 9 - Fri, Jan 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$82 Roundtrip, found 6 days ago
$82
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Jan 9 from Raleigh - Durham Intl. to Westchester County, returning Fri, Jan 16, priced at $82 found 6 days ago
Fri, Jan 9 - Fri, Jan 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Jan 9 from Raleigh - Durham Intl. to Westchester County, returning Fri, Jan 16, priced at $87 found 6 days ago
Fri, Jan 9 - Fri, Jan 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$92 Roundtrip, found 6 days ago
$92
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Jan 9 from Raleigh - Durham Intl. to Westchester County, returning Fri, Jan 16, priced at $92 found 6 days ago
Fri, Jan 16 - Mon, Jan 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 16 from Raleigh - Durham Intl. to Westchester County, returning Mon, Jan 19, priced at $102 found 2 days ago
Fri, Jan 9 - Mon, Jan 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$116 Roundtrip, found 5 days ago
$116
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Jan 9 from Orlando Intl. to Stewart Intl., returning Mon, Jan 12, priced at $116 found 5 days ago
Fri, Jan 9 - Sun, Jan 18
MCO
Orlando Intl.
HPN
Westchester County
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jan 9 from Orlando Intl. to Westchester County, returning Sun, Jan 18, priced at $118 found 1 day ago
Fri, Dec 5 - Sun, Dec 14
MCO
Orlando Intl.
SWF
Stewart Intl.
$118 Roundtrip, found 4 hours ago
$118
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, Dec 5 from Orlando Intl. to Stewart Intl., returning Sun, Dec 14, priced at $118 found 4 hours ago
Fri, Dec 5 - Mon, Dec 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$120 Roundtrip, found 5 hours ago
$120
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Dec 5 from Orlando Intl. to Stewart Intl., returning Mon, Dec 15, priced at $120 found 5 hours ago
Fri, Dec 5 - Mon, Dec 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$120 Roundtrip, just found
$120
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Dec 5 from Orlando Intl. to Stewart Intl., returning Mon, Dec 8, priced at $120 just found
Fri, Jan 9 - Mon, Jan 12
CHS
Charleston Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 10 hours ago
$122
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Fri, Jan 9 from Charleston Intl. to Stewart Intl., returning Mon, Jan 12, priced at $122 found 10 hours ago

New Windsor Flight Information

Traveling To
New Windsor
Destination Airport IATA Code
NYC
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$82
Earliest Departing Flight
Latest Departing Flight

Flights Review

Oct 14, 2019

Newark airport is a pain...but it's not United's fault. The actual flight was just fine.

A verified traveler
Philadelphia to Newark · United

Book Your Flight & Hotel Together & Save

New Windsor economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh
3.0-star property

The Crossroads Hotel, Newburgh

Dec 5 - Dec 7

2 night stay

Atlanta (ATL) to Newburgh (SWF)

Frontier Airlines • Roundtrip • Coach
Price was $279, price is now $235 per person
$235
per person
found 1 day ago
Sleep Inn & Suites Middletown - Goshen
2.5-star property

Sleep Inn & Suites Middletown - Goshen

Dec 19 - Dec 22

3 night stay

Atlanta (ATL) to Newburgh (SWF)

Spirit Airlines • Roundtrip • Coach
Price was $498, price is now $408 per person
$408
per person
found 1 day ago
Wildflower Farms, Auberge Collection
5.0-star property

Wildflower Farms, Auberge Collection

Dec 20 - Dec 27

7 night stay

Charleston (CHS) to Newburgh (SWF)

Delta • Coach

Newburgh (SWF) to Charleston (CHS)

Spirit Airlines • Coach
Save 100% on your flight
Price was $4,907, price is now $4,061 per person
$4,061
per person
found 1 day ago
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New Windsor premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen
2.5-star property

Sleep Inn & Suites Middletown - Goshen

8.4/10 Very Good! (1,031 reviews)

Dec 8 - Dec 11

3 night stay

Atlanta (ATL) to Newburgh (SWF)

Spirit Airlines • PremiumEconomy

Newburgh (SWF) to Atlanta (ATL)

Frontier Airlines • PremiumEconomy
Price was $315, price is now $279 per person
$279
per person
found 1 day ago
Great property close to legoland. We saw some ants coming out from an outlet into our room on the second day. We quickly made sure to put our food items in the fridge.

Reviewed on Apr 28, 2025

Courtyard by Marriott Newburgh Stewart Airport
3.0-star property

Courtyard by Marriott Newburgh Stewart Airport

8.2/10 Very Good! (685 reviews)

Dec 8 - Dec 11

3 night stay

Atlanta (ATL) to Newburgh (SWF)

Spirit Airlines • PremiumEconomy

Newburgh (SWF) to Atlanta (ATL)

Frontier Airlines • PremiumEconomy
Price was $369, price is now $369 per person
$369
per person
found 1 day ago
Just didn’t like the air wasn’t on

Reviewed on May 13, 2023

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New Windsor first class flight packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0-star property

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

8.4/10 Very Good! (1,014 reviews)

Dec 10 - Dec 12

2 night stay

Atlanta (ATL) to Newburgh (SWF)

American Airlines • Roundtrip • FirstClass
Price was $474, price is now $474 per person
$474
per person
found 20 hours ago
comfortable and clean

Reviewed on Jun 5, 2025

Resorts World Catskills Casino
4.5-star property

Resorts World Catskills Casino

8.6/10 Excellent! (1,088 reviews)

Dec 24 - Dec 29

5 night stay

San Juan (SJU) to Newburgh (SWF)

United • FirstClass

Newburgh (SWF) to San Juan (SJU)

American Airlines • FirstClass
Price was $1,448, price is now $1,223 per person
$1,223
per person
found 1 day ago
The room was big, good view. Casino was smoke free,and clean.

Reviewed on Aug 28, 2025

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New Windsor

Save more on flights to New Windsor while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to New Windsor

Now it is easier than ever to find a discount New Windsor flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To New Windsor

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for New Windsor flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to New Windsor a breeze.

Frequently asked questions

Which airlines fly to New Windsor?
You can choose from 20 airlines with services to Liberty Intl. Airport (EWR), the leading airport in the city. With plenty of options, you're bound to pick up a fabulous deal. Here are some of the favorite international airlines that'll get you to New Windsor — and then exploring every nook and cranny of this city:

  • United Airlines - 1,152 flights to New Windsor per month
  • Porter Airlines - 232 flights to New Windsor per month
  • Air Canada - 187 flights to New Windsor per month

How much is a flight to New Windsor?
Prices for return flights to New Windsor this past week fluctuated between $82 and $122. If you were traveling one-way out of Raleigh (RDU), you could have bagged ticket prices from as low as $41.
How to book the cheapest flight to New Windsor?
With some of the best flight deals around, you can jet for less with Orbitz. The following useful tips will help you pick up cheap flights to New Windsor — and leave you with cash to spare:

  • Consider departing from or arriving at alternative airports to save on your airfare. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list any available options.
  • If your plans aren't written in stone, click on the 'Show flexible dates' option to check out the flight deals for different departure dates. You may find a cheaper fare.
  • You can also select the 'Show options' link to filter results for your preferred airline, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd like to fly.
  • The early bird catches the most impressive deals, so book as soon as you know your travel dates. The cheapest fares sell fast and prices normally increase as the departure date nears.
  • Bundle your hotels, flights and car rental into a package deal and score great discounts. Save your hard-earned dollars for things that really excite you, like exploring New Windsor.
  • Flying during peak season means expensive airfares. If possible, plan your vacation outside of popular dates, such as school breaks, Thanksgiving and Easter.

What is the best time to book a flight to New Windsor?
If possible, purchase your flights to New Windsor in January. This is the best month to reserve low airfares, followed by February and August. With a bit of patience and planning, you're guaranteed to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to New Windsor?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days to purchase seats to New Windsor. The vacation of your dreams starts with an incredible flight deal!
What is the cheapest day of the week to fly to New Windsor?
Based on Orbitz data from 2020, Monday is normally the best day to get cheap flights to New Windsor. Tuesday also has budget-friendly fares whereas Saturday has the most expensive ticket prices. Although leaving at the weekend may be more convenient, you'll have more money in your pocket to play with if you fly out earlier in the week.
What is the cheapest month to fly to New Windsor?
If you're flexible with your travel dates, think about leaving in August. Orbitz data shows that this is generally the best month to take off if you're after cheap flights to New Windsor. As you might imagine, fares rise in the busy month of June and flights get snapped up fast.
Which airlines allow free cancellation?
If you're worried your travel plans may change, Orbitz can help you lock in a flexible ticket. All you need to do is select "Filter by flexible change policies" when searching for your New Windsor flights. We'll show you all the airlines that offer free cancellation and no change fees — along with awesome low prices.
What do I need for the flight to New Windsor?
The key to a comfortable and stress-free flight is to prepare well. Listed below are some tips that'll help get you ready for your journey:

  • Before you step on board the plane, you'll need to present some type of government-issued ID, such as a passport. You'll also need your boarding pass. If you're traveling with children, check with your airline about which documents they require — if any.
  • Take some activities to keep you busy on your trip to New Windsor. Books and electronic gadgets like tablets and e-readers are perfect. Remember to take a refillable water bottle as well. Even on a short flight, it's important to stay well-hydrated.
  • Whatever the weather's doing outside, plane cabins can get seriously cold. Bring a light jacket on board to keep yourself cozy.

How do I get cheap first-class/business deals to New Windsor?
There are ways of booking first or business-class airfares to New Windsor that won't burn through your budget. Claim a seat at the front of the plane for less with these handy tips:

  • Flexibility is key. By being open to other travel dates, you'll have more chances of finding a deal on business or first-class airfares.
  • A lot of low-cost carriers these days have comfortable business or premium-class seating without the hefty fees.
  • Bid for an upgrade in online auctions (if available) or upgrade with points earned through loyalty programs.

What is the best time to go to New Windsor?
If you want to immerse yourself in the culture of New Windsor in the peak season, April, May and July are the best months to visit. June 20 marks the beginning of summertime in the Northern Hemisphere and is a fantastic time to go if you enjoy the great outdoors. At this time of the year, average daily temperatures generally range from 60 ºF to 80 ºF.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.