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$96 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 11/18. 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
0 bags

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Best Caribbean Flight Deals

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

Montego Bay
Montego Bay2 stops$956
Santo Domingo
Santo Domingo2 stops$1,002
Nassau
Nassau1 stop$496

Good to know

Low season

September

High season

April

Cheapest flight

$96
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 79% increase in price.
Flight from Stewart Intl. to San Juan

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

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 11% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
7.5
JetBlueOverall score based on 3672 reviews
8.2Crew
7.7Boarding
7.8Comfort
7.4Entertainment
7.0Food
Airline reviews

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

8.0 ExcellentDaniel, Sep 2024JFK - CUN
Read more JetBlue reviews

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 flight was excellent. The crew was welcoming and attentive.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

Got on quickly and easily. When it turned out the other two seats in my row would be occupied, a nearby flight attendant immediately let me know that I could move one row behind me since it was an empty row, I moved into the window seat where I could relax enough to take a little nap. Can’t ask for much more.

We had a 40 mins delay, but the pilot was good about keeping up informed. No food/snacks or drinks when u in the air-they have to be purchased. They charge for every single thing .

I’m not a fan of Spirit Airlines from a not-so-good experience the last time & I swore I would not fly this airline again- bc they charge for EVERYTHING. I only flew Spirit this time bc it wasn’t my choice. I decided to use a “Mystery Ticket” bc of the great price, not knowing it would choose this airline! I found out on this trip how they pick a random seat with a “sticker” for a prize-are we in first grade? just doesn’t seem right & now the first 3 or 4 rows get special treatment-we all paid for our tickets, not just them.

particularly nothing to like plane just turned to be a hmm flying bus, yet in buses from another country at least drink and snack are free ... and seat could be just a bit more ..adjustable? ok ok i know i am asking for too much but ..dreaming is not forbidden yet

Fantastic !!! Seamless boarding. Meticulously clean. We left and arrived early.

The flight was delayed, and we waited for more than an hour on the plane.

Comfortable and plenty of. Having to buy water and coffee, though is ridiculous!

Better overall experience from my first flight with Spirit several years ago. Efficient boarding (albeit I arrived after all rows were called) and flight actually left earlier than planned. I am still baffled by being charged for everything, even a non-alcoholic beverage. And there is definitely less seat room which makes a flight that’s more than 2 hours really uncomfortable.

Check in was made easy with the ladies at the luggage. they were fast and so kind. You should pay them more.

This was the best spirit airlines fight I have ever had. I take spirit up to 3 or more times a year and I am ready to be the Jared of spirit. 🤪 Best flight ever. Everyone was great. I hope my return flight is the same. When you're traveling with a 9 month old you need a different type of care and accommodation. I didn't ask the staff for anything but I didn't have any added stress.

Book cheap flights from Stewart Intl. to Caribbean

Recent round-trip flight deals

11/15ven.
2 stops
12h 55mSWF-SJU
11/17dim.
1 stop
17h 00mSJU-SWF
$305
11/18lun.
1 stop
7h 59mSWF-SJU
11/24dim.
1 stop
17h 31mSJU-SWF
$316
11/18lun.
2 stops
24h 56mSWF-SJU
11/24dim.
1 stop
17h 31mSJU-SWF
$321
11/15ven.
2 stops
12h 55mSWF-SJU
11/24dim.
1 stop
17h 31mSJU-SWF
$352
10/13dim.
3 stops
41h 08mSWF-SJU
10/19sam.
2 stops
15h 14mSJU-SWF
$447
10/4ven.
3 stops
40h 45mSWF-SJU
10/10jeu.
3 stops
29h 35mSJU-SWF
$458
10/4ven.
2 stops
24h 02mSWF-SJU
10/10jeu.
3 stops
29h 35mSJU-SWF
$459
10/4ven.
2 stops
24h 02mSWF-SJU
10/10jeu.
2 stops
23h 04mSJU-SWF
$465
11/18lun.
1 stop
8h 20mSWF-NAS
11/24dim.
1 stop
7h 10mNAS-SWF
$496
12/16lun.
1 stop
6h 20mSWF-NAS
12/20ven.
1 stop
10h 22mNAS-SWF
$506

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Recent one-way flight deals

11/18lun.
1 stop
7h 59mSWF-SJU
$96
11/18lun.
2 stops
23h 01mSWF-SJU
$101
11/15ven.
2 stops
20h 01mSWF-SJU
$130
12/13ven.
1 stop
7h 05mSWF-NAS
$170
10/20dim.
3 stops
41h 08mSWF-SJU
$176
11/14jeu.
2 stops
25h 01mSWF-MBJ
$177
12/30lun.
1 stop
24h 48mSWF-NAS
$180
10/6dim.
2 stops
24h 25mSWF-SJU
$191
12/30lun.
1 stop
24h 48mSWF-NAS
$191
11/25lun.
1 stop
26h 34mSWF-AUA
$192

Search by stops

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Last minute flights from New Windsor to Caribbean

Last minute flight, train and bus deals

9/22dim.
multi-stop
25h 33mSWF-PUJ
9/25mer.
multi-stop
20h 47mPUJ-SWF
$487
9/22dim.
multi-stop
25h 33mSWF-PUJ
9/25mer.
multi-stop
20h 47mPUJ-SWF
$488
9/23lun.
multi-stop
27h 39mSWF-NAS
9/25mer.
multi-stop
22h 45mNAS-SWF
$643

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Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports