$112+ Cheap flights from New Windsor (SWF) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
May 24 — May 311
Round-trip
1 adult, Economy
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Cheapest flights from Stewart to CaribbeanExplore the most affordable flight options available from Stewart to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2026.
Explore the most affordable flight options available from Stewart to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
SWF
- SJU
1 stop7h 48m
Multiple Airlines
Tue 8/258:00 am
SJU
- SWF
1 stop27h 25m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:28 am
SWF
- SJU
1 stop29h 37m
Multiple Airlines
Thu 9/36:00 am
SJU
- SWF
1 stop12h 40m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sat 5/23:21 am
SJU
- SWF
1 stop7h 47m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:05 pm
SWF
- SJU
2 stops20h 04m
Multiple Airlines
Tue 8/258:00 am
SJU
- SWF
1 stop27h 25m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1210:28 am
SWF
- SJU
1 stop10h 20m
Multiple Airlines
Sat 7/185:15 pm
SJU
- SWF
2 stops16h 23m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1210:28 am
SWF
- SJU
1 stop10h 20m
Multiple Airlines
Wed 7/155:15 pm
SJU
- SWF
2 stops16h 23m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- SJU
1 stop10h 23m
Multiple Airlines
Wed 7/155:15 pm
SJU
- SWF
2 stops16h 23m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Thu 4/308:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:05 pm
SWF
- SJU
2 stops12h 32m
Multiple Airlines
Wed 7/16:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:28 am
SWF
- SJU
1 stop29h 30m
Multiple Airlines
Sat 8/223:23 pm
SJU
- SWF
1 stop20h 47m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Sat 5/22:59 am
SJU
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- AUA
1 stop28h 08m
Multiple Airlines
Sat 7/113:41 pm
AUA
- SWF
1 stop17h 57m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$393
Best flights from Stewart to CaribbeanDiscover carefully curated flight deals from Stewart to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2026.
Discover carefully curated flight deals from Stewart to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
SWF
- SJU
1 stop7h 48m
Multiple Airlines
Tue 8/258:00 am
SJU
- SWF
1 stop27h 25m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- AUA
1 stop28h 08m
Multiple Airlines
Sat 7/113:41 pm
AUA
- SWF
1 stop17h 57m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:56 pm
SWF
- SJU
1 stop11h 59m
Multiple Airlines
Wed 7/15:15 pm
SJU
- SWF
2 stops16h 23m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/910:28 am
SWF
- SJU
1 stop10h 20m
Multiple Airlines
Wed 8/126:31 pm
SJU
- SWF
1 stop14h 27m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$432
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- SJU
1 stop10h 23m
Multiple Airlines
Wed 7/86:31 pm
SJU
- SWF
1 stop14h 27m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- SJU
1 stop10h 20m
Multiple Airlines
Sat 7/115:38 pm
SJU
- SWF
2 stops16h 00m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:56 am
SWF
- SJU
2 stops19h 30m
Multiple Airlines
Sat 9/55:01 pm
SJU
- SWF
1 stop17h 22m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2610:28 am
SWF
- SJU
1 stop10h 20m
Multiple Airlines
Sat 8/16:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:05 pm
SWF
- SJU
2 stops12h 10m
Multiple Airlines
Sun 6/146:16 pm
SJU
- SWF
1 stop14h 33m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- NAS
1 stop26h 05m
Multiple Airlines
Wed 4/294:00 pm
NAS
- SWF
1 stop18h 55m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:45 am
SWF
- PUJ
1 stop8h 40m
Multiple Airlines
Sun 5/1711:35 am
PUJ
- SWF
1 stop23h 20m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$484
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2012:05 pm
SWF
- BQN
2 stops38h 00m
Multiple Airlines
Sat 8/2212:28 pm
BQN
- SWF
1 stop20h 30m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$485
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:05 pm
SWF
- SJU
2 stops12h 36m
Multiple Airlines
Wed 7/156:31 pm
SJU
- SWF
1 stop14h 27m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:40 am
SWF
- BQN
1 stop14h 03m
Multiple Airlines
Sat 5/22:48 am
BQN
- SWF
1 stop8h 20m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Sat 5/22:48 am
BQN
- SWF
1 stop8h 20m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$493
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/210:28 am
SWF
- NAS
1 stop9h 02m
Multiple Airlines
Wed 7/84:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:05 pm
SWF
- SJU
2 stops12h 23m
Multiple Airlines
Wed 7/226:31 pm
SJU
- SWF
1 stop14h 27m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$501
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:39 am
SWF
- PUJ
1 stop10h 46m
Multiple Airlines
Fri 6/121:10 pm
PUJ
- SWF
2 stops22h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$501
This eDestinos deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:41 am
SWF
- PUJ
1 stop10h 44m
Multiple Airlines
Sun 6/711:35 am
PUJ
- SWF
1 stop21h 14m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:28 am
SWF
- SJU
1 stop10h 20m
Multiple Airlines
Tue 8/185:38 pm
SJU
- SWF
2 stops17h 47m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:38 am
SWF
- SJU
1 stop7h 34m
Multiple Airlines
Wed 6/246:05 pm
SJU
- SWF
1 stop14h 53m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:56 pm
SWF
- SDQ
2 stops39h 10m
Multiple Airlines
Sat 7/41:57 pm
SDQ
- SWF
1 stop19h 41m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:40 am
SWF
- PUJ
1 stop8h 45m
Multiple Airlines
Sun 5/311:35 am
PUJ
- SWF
1 stop23h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$532
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Wed 4/292:38 am
BQN
- SWF
1 stop8h 30m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:05 pm
SWF
- NAS
2 stops20h 50m
Multiple Airlines
Wed 7/154:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$538
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:13 pm
SWF
- AUA
2 stops46h 23m
Multiple Airlines
Sat 7/113:41 pm
AUA
- SWF
1 stop17h 57m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:11 pm
SWF
- BQN
2 stops13h 32m
Multiple Airlines
Wed 4/292:38 am
BQN
- SWF
1 stop8h 30m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$540
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:05 pm
SWF
- NAS
2 stops20h 50m
Multiple Airlines
Sat 7/184:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$548
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- KIN
1 stop26h 27m
Multiple Airlines
Sat 7/111:00 pm
KIN
- SWF
1 stop19h 38m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:05 pm
SWF
- BQN
2 stops13h 57m
Multiple Airlines
Sat 5/304:28 pm
BQN
- SWF
1 stop16h 30m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$553
Last-minute flights from Stewart to CaribbeanDiscover last-minute flight deals from Stewart to Caribbean. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Caribbean. Data last updated April 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:40 am
SWF
- PUJ
1 stop8h 45m
Multiple Airlines
Sun 4/2611:35 am
PUJ
- SWF
1 stop23h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Thu 4/308:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Sat 5/22:59 am
SJU
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- NAS
1 stop26h 05m
Multiple Airlines
Wed 4/294:00 pm
NAS
- SWF
1 stop18h 55m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Sat 5/22:48 am
BQN
- SWF
1 stop8h 20m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$493
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Wed 4/292:38 am
BQN
- SWF
1 stop8h 30m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sat 5/23:21 am
SJU
- SWF
1 stop7h 47m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:46 pm
SWF
- SJU
2 stops13h 03m
Multiple Airlines
Sat 5/23:21 am
SJU
- SWF
1 stop7h 47m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:40 am
SWF
- BQN
1 stop14h 03m
Multiple Airlines
Sat 5/22:48 am
BQN
- SWF
1 stop8h 20m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:40 am
SWF
- PUJ
1 stop8h 45m
Multiple Airlines
Sun 5/311:35 am
PUJ
- SWF
1 stop23h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$532
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:45 am
SWF
- PUJ
1 stop8h 40m
Multiple Airlines
Sun 5/1711:35 am
PUJ
- SWF
1 stop23h 20m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$484
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:45 am
SWF
- PUJ
1 stop28h 55m
Multiple Airlines
Sun 5/2411:35 am
PUJ
- SWF
1 stop21h 16m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$483
One-way flights from Stewart to CaribbeanSearch for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
Search for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:45 am
SWF
- SJU
1 stop24h 38m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:05 pm
SWF
- SJU
1 stop27h 07m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/231:00 pm
SWF
- SJU
1 stop26h 58m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- SJU
1 stop28h 29m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:45 am
SWF
- PUJ
1 stop25h 45m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2110:28 am
SWF
- AUA
1 stop28h 08m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:05 pm
SWF
- SJU
1 stop28h 29m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:45 am
SWF
- STI
1 stop27h 35m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2810:28 am
SWF
- AUA
1 stop27h 59m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- STI
1 stop26h 17m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:45 am
SWF
- NAS
1 stop26h 05m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$182
Find flight deals from Stewart to Caribbean
Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated April 24, 2026.
Round-trip from | $325 (Kiwi.com) |
|---|---|
One-way from | $112 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $346 |
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2026.
Use the filters below to find and compare flights from New Windsor to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 8/20
1:00 pm-8:48 pm
1 stop7h 48m
San Juan Luis Munoz Marin Intl
Tue 8/25
8:00 am-11:25 am
1 stop27h 25m
$325
New WindsorOranjestad
SWF - AUA
SWFAUA
New Windsor Stewart
Sun 7/5
10:28 am-2:36 pm
1 stop28h 08m
Oranjestad Reina Beatrix
Sat 7/11
3:41 pm-9:38 am
1 stop17h 57m
$393
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 6/24
7:56 pm-7:55 am
1 stop11h 59m
San Juan Luis Munoz Marin Intl
Wed 7/1
5:15 pm-9:38 am
2 stops16h 23m
$420
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 8/9
10:28 am-8:48 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Wed 8/12
6:31 pm-8:58 am
1 stop14h 27m
$432
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 7/5
10:28 am-8:51 pm
1 stop10h 23m
San Juan Luis Munoz Marin Intl
Wed 7/8
6:31 pm-8:58 am
1 stop14h 27m
$444
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 7/5
10:28 am-8:48 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Sat 7/11
5:38 pm-9:38 am
2 stops16h 00m
$449
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Fri 8/28
10:56 am-6:26 am
2 stops19h 30m
San Juan Luis Munoz Marin Intl
Sat 9/5
5:01 pm-10:23 am
1 stop17h 22m
$455
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 7/26
10:28 am-8:48 pm
1 stop10h 20m
San Juan Luis Munoz Marin Intl
Sat 8/1
6:00 am-9:38 am
1 stop27h 38m
$459
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 6/10
12:05 pm-12:15 am
2 stops12h 10m
San Juan Luis Munoz Marin Intl
Sun 6/14
6:16 pm-8:49 am
1 stop14h 33m
$460
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
Sun 4/26
11:45 am-1:50 pm
1 stop26h 05m
Nassau Intl
Wed 4/29
4:00 pm-10:55 am
1 stop18h 55m
$478
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Stewart to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Stewart with our price prediction graph.
SWF-SJU
SWF-AUA
SWF-NAS
SWF-PUJ
SWF-BQN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from New Windsor to Caribbean
SWF-0CB
SWF-SJU
SWF-AUA
SWF-NAS
SWF-PUJ
No data available for this route at this time. Please check back soon.
Related info for your journey
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