$125+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Aug 22 — Aug 291
Round-trip
1 adult, Economy
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Find cheap flights from Stewart to Caribbean with Cheapflights
1. Tell us where you want to go
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 July 23, 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 July 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sun 10/1111:53 am
SWF
- SJU
1 stop11h 45m
Multiple Airlines
Wed 10/145:12 pm
SJU
- SWF
1 stop16h 16m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sun 10/1111:53 am
SWF
- SJU
1 stop11h 45m
Multiple Airlines
Wed 10/215:12 pm
SJU
- SWF
1 stop16h 36m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sun 10/187:14 pm
SWF
- SJU
1 stop28h 43m
Multiple Airlines
Wed 10/215:12 pm
SJU
- SWF
1 stop16h 36m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/307:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 10/810:18 am
SWF
- SJU
1 stop13h 20m
Multiple Airlines
Wed 10/145:12 pm
SJU
- SWF
1 stop16h 16m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/307:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Sun 9/66:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/37:30 pm
SWF
- SJU
1 stop20h 41m
Multiple Airlines
Sun 9/66:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 stop27h 11m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/2912:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/2711:13 am
SWF
- SJU
1 stop12h 44m
Multiple Airlines
Wed 9/305:12 pm
SJU
- SWF
1 stop16h 26m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/2612:05 pm
SWF
- BQN
2 stops14h 05m
Multiple Airlines
Thu 8/2712:04 pm
BQN
- SWF
1 stop22h 02m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 10/1811:53 am
SWF
- NAS
1 stop7h 22m
Multiple Airlines
Wed 10/214:00 pm
NAS
- SWF
1 stop17h 48m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$443
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 July 23, 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 July 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 10/1111:53 am
SWF
- SJU
1 stop11h 45m
Multiple Airlines
Wed 10/145:12 pm
SJU
- SWF
1 stop16h 16m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 10/1510:18 am
SWF
- SJU
1 stop13h 20m
Multiple Airlines
Sun 10/189:49 pm
SJU
- SWF
2 stops13h 47m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/2710:33 am
SWF
- SJU
1 stop9h 19m
Multiple Airlines
Mon 8/318:57 pm
SJU
- SWF
1 stop14h 11m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 10/1811:53 am
SWF
- NAS
1 stop7h 22m
Multiple Airlines
Wed 10/214:00 pm
NAS
- SWF
1 stop17h 48m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/512:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 8/103:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/57:58 pm
SWF
- BQN
1 stop15h 06m
Multiple Airlines
Mon 8/173:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 7/21. 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
- PUJ
1 stop9h 29m
Multiple Airlines
Wed 9/21:29 pm
PUJ
- SWF
2 stops29h 11m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 9/37:30 pm
SWF
- NAS
1 stop19h 15m
Multiple Airlines
Sun 9/611:30 am
NAS
- SWF
1 stop7h 10m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/1512:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 8/173:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 9/1111:06 am
SWF
- PUJ
1 stop9h 19m
Multiple Airlines
Sun 9/1311:35 am
PUJ
- SWF
1 stop22h 56m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$489
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/610:33 am
SWF
- BQN
1 stop15h 37m
Multiple Airlines
Tue 8/1112:04 pm
BQN
- SWF
2 stops23h 21m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 8/812:05 pm
SWF
- BQN
2 stops14h 05m
Multiple Airlines
Mon 8/173:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$528
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/277:31 pm
SWF
- NAS
1 stop14h 59m
Multiple Airlines
Sun 8/3011:30 am
NAS
- SWF
1 stop7h 11m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$544
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/411:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Fri 8/73:10 am
BQN
- SWF
1 stop30h 43m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Sun 8/231:00 pm
SWF
- NAS
1 stop21h 30m
Multiple Airlines
Thu 8/2711:00 am
NAS
- SWF
1 stop7h 41m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/2810:56 am
SWF
- PUJ
1 stop9h 29m
Multiple Airlines
Sun 8/3011:35 am
PUJ
- SWF
1 stop23h 31m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Mon 8/245:39 pm
SWF
- PUJ
1 stop23h 01m
Multiple Airlines
Sat 8/296:25 pm
PUJ
- SWF
2 stops24h 16m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$561
This eDestinos deal was found by Cheapflights users on 7/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:28 am
SWF
- SJU
1 stop14h 00m
Multiple Airlines
Mon 8/310:48 pm
SJU
- SWF
1 stop12h 20m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/2212:05 pm
SWF
- NAS
2 stops20h 50m
Multiple Airlines
Thu 8/2711:30 am
NAS
- SWF
1 stop7h 11m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Tue 9/111:48 am
SWF
- PUJ
2 stops22h 36m
Multiple Airlines
Sun 9/611:35 am
PUJ
- SWF
1 stop23h 51m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$579
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/1912:05 pm
SWF
- NAS
2 stops20h 50m
Multiple Airlines
Thu 8/2711:30 am
NAS
- SWF
1 stop7h 11m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Mon 8/245:39 pm
SWF
- PUJ
2 stops40h 45m
Multiple Airlines
Sun 9/611:35 am
PUJ
- SWF
1 stop23h 51m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 8/812:05 pm
SWF
- NAS
2 stops20h 50m
Multiple Airlines
Sat 8/154:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$588
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Mon 8/245:39 pm
SWF
- PUJ
1 stop23h 01m
Multiple Airlines
Sun 8/3011:35 am
PUJ
- SWF
1 stop23h 31m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$602
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/2112:17 pm
SWF
- SJU
2 stops13h 58m
Multiple Airlines
Mon 8/248:57 pm
SJU
- SWF
1 stop14h 11m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$654
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Tue 9/111:48 am
SWF
- SJU
1 stop8h 04m
Multiple Airlines
Tue 9/88:57 pm
SJU
- SWF
2 stops14h 42m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$663
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/610:33 am
SWF
- SJU
1 stop8h 59m
Multiple Airlines
Mon 8/103:10 am
SJU
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$667
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/1412:16 pm
SWF
- SJU
2 stops13h 34m
Multiple Airlines
Sun 9/206:42 pm
SJU
- SWF
2 stops16h 54m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$671
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Tue 8/411:48 am
SWF
- SJU
1 stop7h 54m
Multiple Airlines
Fri 8/1410:48 pm
SJU
- SWF
2 stops12h 37m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Fri 8/1412:17 pm
SWF
- SJU
2 stops9h 26m
Multiple Airlines
Mon 8/1710:48 pm
SJU
- SWF
1 stop12h 20m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$708
Last-minute flights from Stewart to CaribbeanDiscover last-minute flight deals from Stewart to Caribbean. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Caribbean. Data last updated July 23, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/512:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 8/103:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/57:58 pm
SWF
- BQN
1 stop15h 06m
Multiple Airlines
Mon 8/173:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 stop27h 11m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 stop27h 11m
Multiple Airlines
Sun 9/66:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Sun 8/231:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Thu 8/276:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Mon 8/245:39 pm
SWF
- SJU
1 stop17h 27m
Multiple Airlines
Thu 8/276:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/2612:05 pm
SWF
- BQN
2 stops14h 05m
Multiple Airlines
Thu 8/2712:04 pm
BQN
- SWF
1 stop22h 02m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/2810:56 am
SWF
- SJU
1 stop15h 19m
Multiple Airlines
Sun 9/66:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/2912:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/2912:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sat 9/55:37 pm
SJU
- SWF
1 stop16h 46m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/307:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/307:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Sun 9/66:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$267
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 July 23, 2026.
Search for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Sun 10/1111:53 am
SWF
- SJU
1 stop11h 45m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/307:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 10/1510:18 am
SWF
- SJU
1 stop13h 20m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/37:30 pm
SWF
- SJU
1 stop20h 41m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 10/1811:53 am
SWF
- SJU
1 stop11h 45m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/231:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 8/2912:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 9/512:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/277:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Fri 9/1111:06 am
SWF
- NAS
1 stop29h 09m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/2612:05 pm
SWF
- BQN
2 stops38h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$187
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 July 23, 2026.
Round-trip from | $189 (Kiwi.com) |
|---|---|
One-way from | $125 (Kiwi.com) |
Popular in | July |
Cheapest in | October |
Average price | $389 |
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 July 23, 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
Sun 10/11
11:53 am-11:38 pm
1 stop11h 45m
San Juan Luis Munoz Marin Intl
Wed 10/14
5:12 pm-9:28 am
1 stop16h 16m
$226
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 10/15
10:18 am-11:38 pm
1 stop13h 20m
San Juan Luis Munoz Marin Intl
Sun 10/18
9:49 pm-11:36 am
2 stops13h 47m
$339
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 8/27
10:33 am-7:52 pm
1 stop9h 19m
San Juan Luis Munoz Marin Intl
Mon 8/31
8:57 pm-11:08 am
1 stop14h 11m
$393
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
Sun 10/18
11:53 am-7:15 pm
1 stop7h 22m
Nassau Intl
Wed 10/21
4:00 pm-9:48 am
1 stop17h 48m
$443
New WindsorAguadilla
SWF - BQN
SWFBQN
New Windsor Stewart
Wed 8/5
12:05 pm-11:04 am
2 stops22h 59m
Aguadilla Borinquen
Mon 8/10
3:10 am-11:08 am
1 stop7h 58m
$444
New WindsorAguadilla
SWF - BQN
SWFBQN
New Windsor Stewart
Wed 8/5
7:58 pm-11:04 am
1 stop15h 06m
Aguadilla Borinquen
Mon 8/17
3:10 am-11:08 am
1 stop7h 58m
$457
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
Fri 8/28
10:56 am-8:25 pm
1 stop9h 29m
Punta Cana
Wed 9/2
1:29 pm-6:40 pm
2 stops29h 11m
$458
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
Thu 9/3
7:30 pm-2:45 pm
1 stop19h 15m
Nassau Intl
Sun 9/6
11:30 am-6:40 pm
1 stop7h 10m
$464
New WindsorAguadilla
SWF - BQN
SWFBQN
New Windsor Stewart
Sat 8/15
12:05 pm-11:04 am
2 stops22h 59m
Aguadilla Borinquen
Mon 8/17
3:10 am-11:08 am
1 stop7h 58m
$473
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
Fri 9/11
11:06 am-8:25 pm
1 stop9h 19m
Punta Cana
Sun 9/13
11:35 am-10:31 am
1 stop22h 56m
$489
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-NAS
SWF-BQN
SWF-PUJ
SWF-SDQ
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-NAS
SWF-BQN
SWF-PUJ
No data available for this route at this time. Please check back soon.
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