$140 Find Cheap Flights from New Windsor to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Caribbean departing on 5/16. 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.
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Flights Deals

Best Caribbean Flight Deals from New Windsor

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$369
Santo Domingo
Santo Domingo2 stops$465
Montego Bay
Montego Bay1 stop$333
Oranjestad
Oranjestad1 stop$483
Nassau
Nassau1 stop$424
Kingston
Kingston1 stop$402
Providenciales
Providenciales2 stops$943
Punta Cana
Punta Cana1 stop$369
Santo Domingo
Santo Domingo2 stops$465
Montego Bay
Montego Bay1 stop$333
Oranjestad
Oranjestad1 stop$483
Nassau
Nassau1 stop$424
Kingston
Kingston1 stop$402
Providenciales
Providenciales2 stops$943

Cheap Flight Deals from New Windsor to Caribbean (SWF-0CB)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Windsor to Caribbean 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.

Recent round-trip flight deals from New Windsor to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from New Windsor to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
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11:55 am - 3:00 pmSWF-SJU
27h 05m1 stop
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8:12 pm - 11:05 amSJU-SWF
14h 53m1 stop
Mon, May 26 - Thu, May 29
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7:18 pm - 7:19 pmSWF-SJU
24h 01m1 stop
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8:24 pm - 7:11 pmSJU-SWF
22h 47m1 stop
Mon, Jun 16 - Thu, Jun 19
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11:55 am - 10:45 amSWF-SJU
22h 50m2 stops
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8:12 pm - 11:05 amSJU-SWF
14h 53m1 stop
Fri, May 16 - Sun, May 18
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11:55 am - 3:00 pmSWF-SJU
27h 05m1 stop
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10:38 am - 11:05 amSJU-SWF
24h 27m2 stops
Mon, May 26 - Thu, May 29
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11:55 am - 3:00 pmSWF-SJU
27h 05m1 stop
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10:38 am - 11:05 amSJU-SWF
24h 27m2 stops
Mon, May 26 - Thu, May 29
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7:18 pm - 8:18 pmSWF-SJU
25h 00m1 stop
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8:12 pm - 6:28 pmSJU-SWF
22h 16m1 stop
Fri, Jun 6 - Sun, Jun 8
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11:55 am - 11:02 amSWF-MBJ
24h 07m1 stop
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12:07 pm - 11:05 amMBJ-SWF
21h 58m1 stop
Fri, May 16 - Sun, May 18
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11:55 am - 11:02 amSWF-MBJ
24h 07m1 stop
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12:07 pm - 11:05 amMBJ-SWF
21h 58m1 stop
Mon, May 19 - Thu, May 22
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7:18 pm - 11:02 amSWF-MBJ
16h 44m1 stop
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10:15 am - 6:28 pmMBJ-SWF
7h 13m1 stop
Mon, Jun 9 - Mon, Jun 16
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7:18 pm - 11:02 amSWF-MBJ
16h 44m1 stop
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10:15 am - 7:11 pmMBJ-SWF
7h 56m1 stop
Mon, Jun 9 - Mon, Jun 23
Useful Info

KAYAK's insights & trends for New Windsor to Caribbean flights

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

How long does a flight from New Windsor to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from New Windsor are to Nassau, which takes 7h 20m, San Juan, which takes 7h 29m, and Kingston, which takes 12h 51m.


Good to know

Cheapest flight$140
Flight from Stewart Intl. to Montego Bay

FAQs - booking Caribbean flights

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

    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 from Stewart Intl. to Caribbean.

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

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

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

    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 from Stewart Intl. to Caribbean 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 from Stewart Intl. to Caribbean?

    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 from Stewart Intl. to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $298 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $357.

Top airlines flying from New Windsor to Caribbean

Need help choosing which airline to fly with from New Windsor to Caribbean? 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.
7.3
JetBlueOverall score based on 2922 reviews
7.5Boarding
7.6Comfort
6.7Food
7.3Entertainment
8.0Crew
Airline reviews

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

10.0 ExcellentAnonymous, Apr 2025LGA - FLL
Read more JetBlue reviews

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

In-flight staff was very helpful and excellent. However, the flight was delayed by 90 minutes. Also the boarding process should be expedited in case of delayed flights. This will help the passengers trying to make international connections.

Kayak sent over to jet blue my account being Mike Callaghan instead of Michael. I have a jet blue account with Michael that was connected

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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