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Find cheap flights from Stewart Intl. to Caribbean from $159

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 5/27. 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
Sat 6/1
Sat 6/8

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Best Caribbean Flight Deals

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

Punta Cana
Punta Cana3 stops$1,197
Montego Bay
Montego Bay2 stops$654
Santo Domingo
Santo Domingo2 stops$510
Oranjestad
Oranjestad3 stops$1,503
Providenciales
Providenciales2 stops$1,015

Good to know

Low season

October

High season

April

Cheapest flight

$159
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from New Windsor to Santo Domingo

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 40% more expensive 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.
7.6
JetBlueOverall score based on 4561 reviews
8.3Crew
7.2Food
7.8Boarding
7.5Entertainment
7.9Comfort
Airline reviews

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.

6.0 GoodOscar, Apr 2024LGA - MCO
Read more about JetBlue reviews

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.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

I booked this flight using JetBlue points and I was just so happy. The plane was so clean, I had every need met. Thank you!!

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

The staff at JFK were rude and unhelpful. I was harassed for the same bag that I used on my flight to jfk with no issues claiming it was the inappropriate size. The women then allowed my travel companion to board with the same size bag because they thought she was more “humble”. Also on the flight when informing the flight attendant that nationals no longer have to fill out the Bahamas immigration form my statement was met with eye rolling and attitude.

One of the crew members, a male complained about my bag being too heavy, which I felt was really unnecessary. I am disabled and would have carried it myself if I thought it was going to be a problem. In addition the landing was rough because everyone gasped in unison which it touched down.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Surly, unhelpful ground staff at JFK. There was a complete lack of empathy—a flawed check-in ordeal caused us to miss our flight. All airlines that I have ever flown would have worked to help me solve the ticket problem. Instead, frontline employees shrugged their shoulders and pointed fingers at us for having made an error. I will do anything to avoid EVER flying on Jet Blue again. It well deserves its low rank among airlines.

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Book cheap flights from Stewart Intl. to Caribbean

Recent round-trip flight deals

5/30Thu
2 stops
16h 00mSWF-SJU
6/5Wed
1 stop
11h 40mSJU-SWF
$332
5/30Thu
2 stops
16h 00mSWF-SJU
6/4Tue
3 stops
32h 10mSJU-SWF
$336
5/30Thu
1 stop
15h 45mSWF-SJU
6/5Wed
1 stop
11h 40mSJU-SWF
$340
5/30Thu
1 stop
15h 45mSWF-SJU
6/4Tue
3 stops
32h 10mSJU-SWF
$344
5/30Thu
2 stops
16h 00mSWF-SJU
6/5Wed
2 stops
28h 05mSJU-SWF
$354
5/30Thu
2 stops
16h 00mSWF-SJU
6/5Wed
3 stops
28h 05mSJU-SWF
$355
5/9Thu
1 stop
15h 45mSWF-SJU
5/11Sat
2 stops
13h 48mSJU-SWF
$374
5/30Thu
3 stops
28h 53mSWF-SJU
6/4Tue
3 stops
32h 10mSJU-SWF
$379
5/30Thu
3 stops
28h 53mSWF-SJU
6/5Wed
3 stops
28h 05mSJU-SWF
$398
5/9Thu
1 stop
14h 34mSWF-SJU
5/11Sat
1 stop
16h 01mSJU-SWF
$427

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Recent one-way flight deals

5/27Mon
1 stop
29h 58mSWF-SDQ
$159
6/2Sun
1 stop
15h 34mSWF-SJU
$168
6/2Sun
1 stop
16h 03mSWF-SDQ
$172
5/12Sun
1 stop
16h 03mSWF-SDQ
$182
5/31Fri
1 stop
15h 50mSWF-SDQ
$185
5/10Fri
2 stops
29h 58mSWF-SDQ
$192
5/10Fri
1 stop
30h 10mSWF-SDQ
$193
6/13Thu
1 stop
14h 47mSWF-SJU
$196
5/5Sun
1 stop
26h 44mSWF-MBJ
$197
5/12Sun
1 stop
26h 35mSWF-MBJ
$199

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Last minute flights from New Windsor to Caribbean

Last minute flight, train and bus deals

5/5Sun
multi-stop
25h 20mSWF-SJU
5/11Sat
multi-stop
13h 48mSJU-SWF
$387
5/5Sun
multi-stop
25h 20mSWF-SJU
5/11Sat
multi-stop
27h 35mSJU-SWF
$454
5/5Sun
multi-stop
25h 20mSWF-SJU
5/11Sat
multi-stop
29h 45mSJU-SWF
$463
5/6Mon
multi-stop
12h 40mSWF-SDQ
5/10Fri
multi-stop
12h 11mSDQ-SWF
$510
5/5Sun
multi-stop
6h 00mSWF-NAS
5/9Thu
multi-stop
25h 06mNAS-SWF
$1,181

Search by stops

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