SWF

$48 Find Cheap Flights to New Windsor

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to New Windsor departing on 1/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to New Windsor

 
These are the airlines KAYAK users have selected most often from within our search results for flights to New Windsor, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to New Windsor, as well as popular online travel agencies
Travelers love KAYAK
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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$98
Overall average: $173
Allegiant Air
Fri 2/6Mon 2/9
FLL - SWF • Non-stop
Cheapest one-way
$47
Typical prices: $56-$229
Allegiant Air
Fri 1/16
FLL - SWF • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue’s Even More Space adds 7” legroom and priority.
Breeze’s Nicest fare offers 39” legroom and free Wi-Fi.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Allegiant Air
Most flights • 10 per week
Breeze Airways
Best reviews • 8.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to New Windsor!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights to New Windsor

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to New Windsor that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to New Windsor

Fri, Feb 6 - Mon, Feb 9
Allegiant Air Logo
7:15 am - 10:19 am
FLL
-
SWF
3h 04mnonstop
Allegiant Air Logo
11:09 am - 2:52 pm
SWF
-
FLL
3h 43mnonstop
$98Allegiant Air
Fri, Jan 16 - Fri, Jan 23
Allegiant Air Logo
7:15 am - 10:19 am
FLL
-
SWF
3h 04mnonstop
Allegiant Air Logo
11:09 am - 2:52 pm
SWF
-
FLL
3h 43mnonstop
$101Allegiant Air
Mon, Feb 2 - Mon, Feb 9
Allegiant Air Logo
7:15 am - 10:19 am
FLL
-
SWF
3h 04mnonstop
Allegiant Air Logo
11:09 am - 2:52 pm
SWF
-
FLL
3h 43mnonstop
$102Allegiant Air
Fri, Jan 30 - Mon, Feb 2
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m1 stop
$104Breeze Airways
Fri, Feb 6 - Mon, Feb 9
Allegiant Air Logo
7:15 am - 10:19 am
FLL
-
SWF
3h 04mnonstop
Allegiant Air Logo
11:09 am - 2:52 pm
SWF
-
FLL
3h 43mnonstop
$104Allegiant Air
Fri, Jan 23 - Mon, Jan 26
Allegiant Air Logo
7:15 am - 10:19 am
FLL
-
SWF
3h 04mnonstop
Allegiant Air Logo
11:09 am - 2:52 pm
SWF
-
FLL
3h 43mnonstop
$106Allegiant Air
Wed, May 6 - Wed, May 13
Breeze Airways Logo
9:45 am - 11:25 am
RDU
-
SWF
1h 40mnonstop
Breeze Airways Logo
12:05 pm - 1:45 pm
SWF
-
RDU
1h 40mnonstop
$107Breeze Airways
Fri, Feb 6 - Mon, Feb 9
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m1 stop
$109Breeze Airways
Fri, Feb 6 - Mon, Feb 9
Allegiant Air Logo
7:15 am - 10:19 am
FLL
-
SWF
3h 04mnonstop
Allegiant Air Logo
11:09 am - 2:52 pm
SWF
-
FLL
3h 43mnonstop
$109Allegiant Air
Thu, Jan 22 - Mon, Jan 26
Multiple Airlines Logo
5:43 pm - 10:19 am
ATL
-
SWF
16h 36m1 stop
Multiple Airlines Logo
11:09 am - 10:24 am
SWF
-
ATL
23h 15m1 stop
$173Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to New Windsor

Get data-powered insights and trends for flights to New Windsor to help you find the cheapest flights, the best time to fly and much more.

How much is a flight to New Windsor?

The average and cheapest price for all round-trip flights to New Windsor from each origin found by users searching on KAYAK in the last month.

On average, a flight to New Windsor costs $163. The cheapest price found on KAYAK in the last 2 weeks cost $48 and departed from Orlando Sanford Intl Airport. The most popular routes on KAYAK are Orlando to New Windsor which costs $178 on average, and Charleston to New Windsor, which costs $298 on average.

See prices from:

What is a good deal for flights to New Windsor?

If you’re looking for cheap airfare to New Windsor, 25% of our users found tickets to New Windsor for the following prices or less: From Orlando Sanford Intl Airport $86 one-way - $130 round-trip, from Orlando Airport $110 one-way - $148 round-trip, from Myrtle Beach $121 one-way - $175 round-trip.

Expert advice

Expert advice for your flight to New Windsor

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Spirit Airlines

Spirit’s Go Big fare includes Big Front Seat and free in-flight Wi-Fi.


Spirit’s Big Front Seat offers 20” width and 11” extra legroom.

Allegiant Air

Allegiant’s Bonus bundle includes a carry-on, seat selection, and ticket change flexibility.


Allegiant’s Trip Flex allows one free flight change or postponement.

Breeze Airways

Breeze’s Nicest fare offers 39” legroom and free Wi-Fi on Airbus A220.


Breeze’s Nicer fare includes extra legroom, priority boarding, and a free checked bag.

Frontier

Frontier’s Premium Bundle offers priority boarding and extra legroom seats.


Frontier’s Economy Bundle includes a carry-on and standard seat choice.

JetBlue

JetBlue’s Even More Space offers up to 7” extra legroom and priority security access.


Enjoy free gate-to-gate Wi-Fi and live TV on JetBlue flights.

Our travel experts
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Chris Dong

Chris Dong

Expert on Breeze Airways

Chris Dong

Chris Dong

Chris is a consumer travel reporter covering aviation, trending travel news, hotels, and loyalty programs—all for leading global publications like Travel + Leisure, The Washington Post, AFAR, and more. In addition to writing, Chris is a video host for Travel + Leisure, giving consumers an inside look at the latest in air travel.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on JetBlue

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more

Good to know - Book Cheap New Windsor Plane Tickets

Low seasonFebruary
Cheapest flight$47
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Fort Lauderdale to Stewart Intl.

When to book flights to New Windsor

Are your dates flexible? Find out the best times to travel to New Windsor based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to New Windsor based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Stewart Intl. flights

  • What airlines fly directly to Stewart International Airport?

    There are several US cities that you can fly direct to Stewart Airport from. Allegiant Air offers direct flights from Punta Gorda (PGD), Orlando (SFB), and Tampa (PIE) in Florida, Savannah (SAV) in Georgia, and Myrtle Beach (MYR) in South Carolina. JetBlue also flies direct to Orlando and Fort Lauderdale (FLL). American Airlines offers direct service to Stewart from Philadelphia. For each of these flights, there is usually at least one departure a week. You can set up an alert with KAYAK to notify you of any changes.

  • Does Stewart International Airport provide assistance for passengers with special needs?

    To ensure you find the increased accessibility assistance you need, you can speak to the airport staff upon your arrival so that they can make the proper arrangements, such as wheelchair services. All the restrooms at the airport are accessible, and there are customer care associates wearing red jackets throughout the terminal ready to assist passengers as well.

  • Is there a bus I can take to New York City from Stewart International Airport?

    The most direct way to get to New York City is the Stewart Airport Express coach service, which leaves from the airport terminal. Tickets are around $20 for adults and about $10 for children aged 5-11 years. There is one departure a day around 5.15 pm and takes about 90min to Port Authority Bus Terminal in New York City.

  • Are there train options from Stewart International Airport?

    There is a shuttle bus from Stewart Airport to Beacon Station Monday to Friday, from around 9.00 am to about 8.25 pm. The trip costs about $1. Or you can take a taxi during off-peak hours. From Beacon Station, you can catch the Metro-North Hudson Line to Grand Central Station. Depending on the train, you may need to transfer. Trains generally run from around 4.30 am to around 11.10 pm with departures every hour or two hours. Tickets vary from peak to off-peak times and may be subject to an extra charge if purchased aboard the train.

  • How far is New Windsor Stewart Airport from central Stewart Intl.?

    The city center of Stewart Intl. is 4 miles from New Windsor Stewart Airport.

  • What is the name of Stewart Intl.’s airport?

    Stewart Intl. is served by New Windsor Stewart Airport, also commonly referred to as Newburgh Stewart, Stewart, or Stewart Intl. The airport code is SWF.

  • How much is a flight to New Windsor?

    On average, a flight to New Windsor costs $163. The cheapest price found on KAYAK in the last 2 weeks cost $48 and departed from Orlando Sanford Intl Airport.

  • What is the cheapest day to fly to New Windsor?

    Based on KAYAK data, the cheapest day to fly to New Windsor is Friday where tickets can be as cheap as $110. On the other hand, the most expensive day to fly is Sunday, where prices are $192 on average.

  • How does KAYAK find such low prices on flights to Stewart Intl.?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Stewart Intl..

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Stewart Intl.?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Stewart Intl. is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Stewart Intl.?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Stewart Intl. with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Stewart Intl.?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Stewart Intl. up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Stewart Intl.

  • Looking for cheap airfare to Stewart Intl.? 25% of our users found round-trip tickets to Stewart Intl. for the following prices or less: From Fort Lauderdale $126, from Orlando $129, from Myrtle Beach $148
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Stewart Intl. flight deals.
  • Stewart International Airport (SWF) services New York City, as well as cities in the Hudson Valley including New Windsor, Newburgh, Beacon, Kingston, Poughkeepsie, New Paltz, and West Point.
  • The airport normally closes at around 1.00 am every day until about 4.00 am, so you should make sure to have transport plans in place if you have a late-night arrival.
  • If you need cash to continue on your journey into New York, there are ATMs by the baggage claim area and at the Welcome Center so that you can withdraw money any time of the day.
  • Car rental companies, including Avis, Enterprise, and Budget, offer pick-up car rentals from Stewart if you prefer to drive into New York from the airport.
  • If you prefer to catch a taxi from the airport, you need to contact the Welcome Center or a customer care representative to help you arrange a ride.
  • There are food services and shops at the airport if you want to grab a drink or a snack before you leave the airport to continue into New York.

Reviews of the top 4 airlines flying to New Windsor

 
See real verified KAYAK customer reviews for airlines flying to New Windsor. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the United States to New Windsor. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to New Windsor? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.2
Breeze AirwaysOverall score based on 255 reviews
8.3Boarding
6.7Food
8.8Crew
6.7Entertainment
8.2Comfort
Airline reviews

Flight departure was 90 min delayed, and the boarding experience was confused, stressful, and generally poor. Additionally, the wifi on the plane was malfunctioning for all but the final 15 min of the flight into ILM.

6.0 GoodDavid, Jan 2026
BDL - ILM
Read more Breeze Airways reviews

Flight departure was 90 min delayed, and the boarding experience was confused, stressful, and generally poor. Additionally, the wifi on the plane was malfunctioning for all but the final 15 min of the flight into ILM.

Great experience and In love flying in and out of Provo airport

You get what you pay for. It’s like a bus but flying. No frills, no snacks. Leg room was fine, boarding was good.

Overall good. Plenty of legroom and fairly comfortable seats. No issues with capacity and the overhead been even though most people brought several carry-ons on. I don’t think Breeze really enforces the pay for a carry-on rule.

Surprised at how much I enjoyed Breeze. Paid for the Nicer upgrade which made it closer in price to a flag ship carrier but with more comfortable seats and much more leg room. Crew was polite and since we brought our food no loss there. Would make the point that the ‘have to pay for a carry-on is BS’. Most people did not and had several. Still was plenty of room in the overheads.

Comfortable seating, adequate space available, nice to have USB port, polite crew.

My experience is typically great with Breeze. This trip wasn’t any different.

This was my first experience with Breeze. The plane was cleaner and more comfortable than any other I've experienced. The process of boarding was streamlined. We boarded early and arrived at our destination 45 minutes early. The only hiccup was my ticket was rejected by TSA PreCheck and I got sent to the back of a very long line at Fort Myers. I entered my information when I bought my ticket, but it apparently didn't connect to my permanent profile. I'll correct that for next time. I was expecting an Allegiant experience, but Breeze was much more upscale. I really, really enjoyed it.

Great experience. Non stop is great in and of itself.

Lady at check in counter helped me get a seat in the cut row all to myself.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

flight cancelled after 2 delays. left us sitting in JFK at 1am. no customer service to assist rebooking.

To not have food or proper snacks on a 5 hour flight was the worst.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

Excellent flight and even arrived 23 min early. No entertainment , or wi fi on board, but I downloaded a couple of movies beforehand which kept me entertained. Really like flying Allegiant airlines.

WE were delayed about an hour and never any communications from the employees working the gate. We also were moved to a total of three gates.

I love how they show love to their customers and care about them too.

I liked how when I got on board how fast we ended up taking off but what I truly disliked was how uncomfortable the seats were. There was truly never a time that I could ever get comfortable during both of my flights. The seats could get away during shorter flights but flights 3 hour plus makes it hard to enjoy.

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Not clean and was told I would get a great seat and it was not great at all

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Flights with popular airlines flying to New Windsor

Flights from the other most popular airlines that fly from the United States to New Windsor according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.