$127+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Apr 11 — Apr 181
Round-trip
1 adult, Economy
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Find cheap flights from Stewart to Caribbean with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 March 12, 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 March 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 6/1110:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sat 6/135:56 pm
SJU
- SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 5/2410:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sat 5/305:56 pm
SJU
- SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 5/2110:28 am
SWF
- SJU
1 stop29h 27m
Multiple Airlines
Wed 5/276:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/1911:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Sun 4/268:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 stop7h 37m
Multiple Airlines
Fri 5/81:59 am
SJU
- SWF
2 stops9h 26m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/2810:28 am
SWF
- SJU
1 stop8h 54m
Multiple Airlines
Sun 5/318:27 pm
SJU
- SWF
1 stop12h 24m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/3110:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sat 8/15:56 pm
SJU
- SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/1911:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sat 4/257:01 pm
SJU
- SWF
2 stops15h 54m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/1011:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Wed 5/138:27 pm
SJU
- SWF
1 stop12h 31m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/1112:15 pm
SWF
- SJU
2 stops11h 09m
Multiple Airlines
Wed 5/1312:57 pm
SJU
- SWF
1 stop21h 58m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 3/7![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 4/911:45 am
SWF
- SDQ
1 stop13h 53m
Multiple Airlines
Wed 4/152:35 pm
SDQ
- SWF
1 stop20h 20m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$399
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 March 12, 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 March 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 5/2110:28 am
SWF
- SJU
1 stop29h 27m
Multiple Airlines
Wed 5/276:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 stop7h 37m
Multiple Airlines
Fri 5/81:59 am
SJU
- SWF
2 stops9h 26m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 3/7![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/1612:05 pm
SWF
- SJU
2 stops11h 54m
Multiple Airlines
Wed 5/2012:57 pm
SJU
- SWF
1 stop20h 41m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 4/911:45 am
SWF
- SDQ
1 stop13h 53m
Multiple Airlines
Wed 4/152:35 pm
SDQ
- SWF
1 stop20h 20m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 3/11. 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
- PUJ
2 stops46h 51m
Multiple Airlines
Sun 5/311:35 am
PUJ
- SWF
1 stop23h 15m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/2810:28 am
SWF
- NAS
1 stop24h 02m
Multiple Airlines
Wed 6/34:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 6/129:39 am
SWF
- PUJ
1 stop10h 46m
Multiple Airlines
Sun 6/1411:35 am
PUJ
- SWF
1 stop21h 14m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 5/2410:28 am
SWF
- NAS
1 stop8h 47m
Multiple Airlines
Wed 5/274:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 3/11. 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
- SJU
1 stop10h 58m
Multiple Airlines
Thu 5/216:09 pm
SJU
- SWF
1 stop14h 42m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/510:29 am
SWF
- STI
1 stop15h 20m
Multiple Airlines
Wed 4/82:46 am
STI
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/1711:45 am
SWF
- NAS
1 stop7h 30m
Multiple Airlines
Thu 5/2112:00 pm
NAS
- SWF
1 stop20h 51m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/2311:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Wed 4/292:59 am
SJU
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 3/7. 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
Wed 5/61:29 pm
PUJ
- SWF
2 stops19h 29m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Tue 8/1111:48 am
SWF
- BQN
1 stop14h 15m
Multiple Airlines
Mon 8/172:58 am
BQN
- SWF
1 stop8h 10m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/1011:45 am
SWF
- AUA
1 stop26h 51m
Multiple Airlines
Sat 5/163:41 pm
AUA
- SWF
1 stop19h 14m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/1711:45 am
SWF
- NAS
1 stop7h 30m
Multiple Airlines
Fri 5/295:30 pm
NAS
- SWF
2 stops17h 55m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$483
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/510:29 am
SWF
- SDQ
1 stop26h 46m
Multiple Airlines
Wed 4/82:52 am
SDQ
- SWF
1 stop8h 03m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$485
This Kiwi.com deal was found by Cheapflights users on 3/11. 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
- BQN
1 stop14h 03m
Multiple Airlines
Sun 4/262:38 am
BQN
- SWF
2 stops8h 53m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$490
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 8/712:15 pm
SWF
- BQN
2 stops13h 48m
Multiple Airlines
Mon 8/172:58 am
BQN
- SWF
1 stop8h 10m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$491
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 3/2210:29 am
SWF
- STI
1 stop15h 20m
Multiple Airlines
Wed 4/82:46 am
STI
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 6/1110:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sun 6/148:27 pm
SJU
- SWF
1 stop12h 22m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 8/812:05 pm
SWF
- PUJ
2 stops20h 10m
Multiple Airlines
Fri 8/141:10 pm
PUJ
- SWF
1 stop26h 40m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 3/8. 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
Wed 4/299:13 pm
PUJ
- SWF
2 stops13h 55m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 3/2210:29 am
SWF
- KIN
1 stop26h 06m
Multiple Airlines
Sat 3/2812:32 pm
KIN
- SWF
1 stop20h 07m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 3/9. 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
- KIN
1 stop27h 27m
Multiple Airlines
Wed 6/33:18 pm
KIN
- SWF
1 stop17h 20m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/411:45 am
SWF
- SJU
1 stop10h 14m
Multiple Airlines
Wed 4/87:54 pm
SJU
- SWF
1 stop15h 01m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/1611:48 am
SWF
- SDQ
2 stops25h 41m
Multiple Airlines
Wed 4/222:35 pm
SDQ
- SWF
1 stop20h 20m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$524
This Kiwi.com deal was found by Cheapflights users on 3/11. 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
Tue 6/92:50 pm
SJU
- SWF
1 stop20h 35m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 3/11. 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
- NAS
2 stops28h 20m
Multiple Airlines
Sat 5/304:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$527
Last-minute flights from Stewart to CaribbeanDiscover last-minute flight deals from Stewart to Caribbean. Data last updated March 12, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Caribbean. Data last updated March 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 3/2210:29 am
SWF
- SJU
1 stop8h 26m
Multiple Airlines
Wed 3/257:54 pm
SJU
- SWF
1 stop13h 45m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/210:29 am
SWF
- SJU
1 stop8h 26m
Multiple Airlines
Wed 4/87:54 pm
SJU
- SWF
1 stop15h 01m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/510:29 am
SWF
- SJU
1 stop25h 20m
Multiple Airlines
Wed 4/87:54 pm
SJU
- SWF
1 stop15h 01m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/510:29 am
SWF
- STI
1 stop15h 20m
Multiple Airlines
Wed 4/82:46 am
STI
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 4/911:45 am
SWF
- SDQ
1 stop13h 53m
Multiple Airlines
Wed 4/152:35 pm
SDQ
- SWF
1 stop20h 20m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/1611:45 am
SWF
- SDQ
1 stop25h 44m
Multiple Airlines
Wed 4/222:35 pm
SDQ
- SWF
1 stop20h 20m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/1911:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Sun 4/268:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/1911:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sat 4/257:01 pm
SJU
- SWF
2 stops15h 54m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 3/7![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 stop7h 37m
Multiple Airlines
Fri 5/81:59 am
SJU
- SWF
2 stops9h 26m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/11. 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
- PUJ
2 stops46h 51m
Multiple Airlines
Sun 5/311:35 am
PUJ
- SWF
1 stop23h 15m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 5/95:15 pm
SJU
- SWF
2 stops17h 40m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$411
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 March 12, 2026.
Search for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/1911:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/911:45 am
SWF
- SJU
1 stop24h 04m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 5/1711:45 am
SWF
- SJU
1 stop29h 31m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/1011:45 am
SWF
- SJU
1 stop31h 37m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/711:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/1211:45 am
SWF
- NAS
1 stop27h 00m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/1911:45 am
SWF
- NAS
1 stop7h 30m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/911:45 am
SWF
- MBJ
1 stop24h 20m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/1211:45 am
SWF
- STI
1 stop14h 04m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 3/8. 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
Deal found 3/8![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/911:45 am
SWF
- STI
1 stop14h 04m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/911:45 am
SWF
- NAS
1 stop26h 05m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$177
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 March 12, 2026.
Round-trip from | $306 (Kiwi.com) |
|---|---|
One-way from | $127 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $296 |
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 March 12, 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 5/21
10:28 am-3:55 pm
1 stop29h 27m
San Juan Luis Munoz Marin Intl
Wed 5/27
6:00 am-9:38 am
1 stop27h 38m
$318
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 4/26
11:45 am-7:22 pm
1 stop7h 37m
San Juan Luis Munoz Marin Intl
Fri 5/8
1:59 am-11:25 am
2 stops9h 26m
$329
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
Fri 4/24
11:40 am-8:25 pm
1 stop8h 45m
Punta Cana
Sun 4/26
11:35 am-10:50 am
1 stop23h 15m
$367
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 5/16
12:05 pm-11:59 pm
2 stops11h 54m
San Juan Luis Munoz Marin Intl
Wed 5/20
12:57 pm-9:38 am
1 stop20h 41m
$394
New WindsorSanto Domingo
SWF - SDQ
SWFSDQ
New Windsor Stewart
Thu 4/9
11:45 am-1:38 am
1 stop13h 53m
Santo Domingo Las Americas
Wed 4/15
2:35 pm-10:55 am
1 stop20h 20m
$399
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
Sun 4/26
11:45 am-10:36 am
2 stops46h 51m
Punta Cana
Sun 5/3
11:35 am-10:50 am
1 stop23h 15m
$450
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
Thu 5/28
10:28 am-10:30 am
1 stop24h 02m
Nassau Intl
Wed 6/3
4:00 pm-9:38 am
1 stop17h 38m
$451
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
Fri 6/12
9:39 am-8:25 pm
1 stop10h 46m
Punta Cana
Sun 6/14
11:35 am-8:49 am
1 stop21h 14m
$454
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
Sun 5/24
10:28 am-7:15 pm
1 stop8h 47m
Nassau Intl
Wed 5/27
4:00 pm-9:38 am
1 stop17h 38m
$456
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Fri 5/15
11:45 am-10:43 pm
1 stop10h 58m
San Juan Luis Munoz Marin Intl
Thu 5/21
6:09 pm-8:51 am
1 stop14h 42m
$457
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-PUJ
SWF-SDQ
SWF-MBJ
SWF-NAS
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-PUJ
SWF-SDQ
SWF-MBJ
What is the cheapest month to book a flight from New Windsor to Caribbean?
Currently, May is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $93). Flying from New Windsor to Caribbean in August is currently the most expensive (average of $138). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated March 12, 2026.
Peruse reviews from past customers who have flown with JetBlue from New Windsor to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.2
Comfort
7.5
Food
6.6
Overall
7.2
Crew
8.0
Boarding
7.4
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Entertainment
7.2
Comfort
7.5
Food
6.6
Overall
7.2
Crew
8.0
Boarding
7.4
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Related info for your journey
Find useful and relevant information for your journey from Stewart to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Stewart to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Stewart to Caribbean by cabin class
Find flights from Stewart to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Stewart and Caribbean flights
Browse other Stewart and Caribbean flight options. Last updated on March 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Stewart to Caribbean flights
Consider these flights traveling from Stewart to Caribbean.
Top airline flying from Stewart to Caribbean
Discover the top airline that operate flights from Stewart to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$336 | FlexibilityNo cancel fee | On-time62% |