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Find cheap flights from Stewart Intl. to Caribbean from $121

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 6/3. 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
Fri 6/7
Fri 6/14

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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 Cana2 stops$523
Santo Domingo
Santo Domingo1 stop$487
Oranjestad
Oranjestad2 stops$841
Nassau
Nassau2 stops$601
Simpson Bay
Simpson Bay3 stops$471
Providenciales
Providenciales2 stops$1,140

Good to know

Cheapest flight

$121
Flight from New Windsor 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 31% 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.
7.6
JetBlueOverall score based on 4525 reviews
7.2Food
7.8Boarding
7.9Comfort
8.3Crew
7.5Entertainment
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.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

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.

Book cheap flights from Stewart Intl. to Caribbean

Recent round-trip flight deals

6/6Thu
1 stop
14h 47mSWF-SJU
6/13Thu
3 stops
30h 26mSJU-SWF
$357
6/6Thu
2 stops
16h 45mSWF-SJU
6/13Thu
3 stops
30h 26mSJU-SWF
$387
6/6Thu
1 stop
14h 47mSWF-SJU
6/13Thu
2 stops
24h 14mSJU-SWF
$413
6/13Thu
1 stop
16h 08mSWF-SJU
6/20Thu
2 stops
11h 47mSJU-SWF
$422
6/13Thu
1 stop
14h 47mSWF-SJU
6/20Thu
3 stops
30h 26mSJU-SWF
$443
7/6Sat
1 stop
16h 21mSWF-SJU
7/10Wed
1 stop
10h 55mSJU-SWF
$446
7/6Sat
1 stop
16h 21mSWF-SJU
7/10Wed
1 stop
7h 23mSJU-SWF
$456
6/13Thu
1 stop
14h 47mSWF-SJU
6/19Wed
2 stops
13h 54mSJU-SWF
$460
7/10Wed
1 stop
14h 24mSWF-SJU
7/20Sat
1 stop
14h 05mSJU-SWF
$473
6/6Thu
3 stops
25h 05mSWF-SJU
6/13Thu
3 stops
30h 26mSJU-SWF
$480

Search by stops

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Recent one-way flight deals

6/3Mon
2 stops
24h 54mSWF-SJU
$121
5/13Mon
2 stops
38h 19mSWF-SJU
$140
5/17Fri
2 stops
28h 59mSWF-SJU
$147
6/8Sat
1 stop
15h 00mSWF-SDQ
$148
6/3Mon
1 stop
14h 25mSWF-SJU
$152
6/6Thu
1 stop
14h 47mSWF-SJU
$156
6/7Fri
2 stops
32h 15mSWF-SJU
$176
6/8Sat
2 stops
14h 43mSWF-SDQ
$176
6/9Sun
1 stop
16h 13mSWF-SJU
$178
6/9Sun
1 stop
16h 13mSWF-SJU
$179

Search by stops

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Last minute flights from New Windsor to Caribbean

Last minute flight, train and bus deals

5/13Mon
multi-stop
38h 19mSWF-SJU
5/30Thu
multi-stop
17h 49mSJU-SWF
$373
5/13Mon
multi-stop
15h 51mSWF-SJU
5/18Sat
multi-stop
19h 10mSJU-SWF
$417
5/13Mon
multi-stop
38h 19mSWF-SJU
5/16Thu
multi-stop
17h 49mSJU-SWF
$427
5/12Sun
multi-stop
16h 03mSWF-SDQ
5/18Sat
multi-stop
17h 54mSDQ-SWF
$434
5/12Sun
multi-stop
16h 03mSWF-SDQ
5/19Sun
multi-stop
28h 49mSDQ-SWF
$436
5/13Mon
multi-stop
16h 20mSWF-SDQ
5/18Sat
multi-stop
17h 54mSDQ-SWF
$442
5/12Sun
multi-stop
16h 03mSWF-SDQ
5/19Sun
multi-stop
20h 20mSDQ-SWF
$518
5/10Fri
multi-stop
18h 26mSWF-SDQ
5/12Sun
multi-stop
17h 32mSDQ-SWF
$609
5/10Fri
multi-stop
18h 26mSWF-SDQ
5/12Sun
multi-stop
26h 01mSDQ-SWF
$625
5/9Thu
multi-stop
17h 29mSWF-SJU
5/12Sun
multi-stop
19h 45mSJU-SWF
$959

Search by stops

Search by price