$134+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
jul. 10 — jul. 171
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 junio 10, 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 junio 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
jue. 8/277:31 pm
SWF
- SJU
1 stop20h 27m
Multiple Airlines
jue. 9/36:00 am
SJU
- SWF
1 stop12h 40m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
jue. 10/810:18 am
SWF
- SJU
1 stop13h 20m
Multiple Airlines
mié. 10/145:12 pm
SJU
- SWF
1 stop16h 16m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
jue. 9/37:30 pm
SWF
- SJU
1 stop20h 28m
Multiple Airlines
dom. 9/66:00 am
SJU
- SWF
1 stop12h 40m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
jue. 8/277:31 pm
SWF
- SJU
1 stop20h 27m
Multiple Airlines
dom. 8/306:00 am
SJU
- SWF
1 stop12h 41m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
dom. 10/1111:53 am
SWF
- SJU
1 stop11h 45m
Multiple Airlines
mié. 10/145:12 pm
SJU
- SWF
1 stop16h 16m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
jue. 8/201:00 pm
SWF
- SJU
1 stop26h 58m
Multiple Airlines
jue. 8/276:00 am
SJU
- SWF
1 stop12h 41m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
jue. 10/810:18 am
SWF
- SJU
1 stop13h 20m
Multiple Airlines
sáb. 10/105:12 pm
SJU
- SWF
1 stop17h 51m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
jue. 8/1310:28 am
SWF
- SJU
1 stop29h 43m
Multiple Airlines
mié. 8/196:00 am
SJU
- SWF
1 stop30h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
jue. 8/611:45 am
SWF
- SJU
1 stop12h 56m
Multiple Airlines
mié. 8/126:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
dom. 10/1111:53 am
SWF
- NAS
1 stop7h 22m
Multiple Airlines
mié. 10/144:00 pm
NAS
- SWF
1 stop17h 28m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
vie. 8/2810:56 am
SWF
- PUJ
1 stop9h 29m
Multiple Airlines
sáb. 9/56:25 pm
PUJ
- SWF
2 stops24h 15m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$482
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
dom. 8/307:31 pm
SWF
- NAS
1 stop14h 59m
Multiple Airlines
dom. 9/611:30 am
NAS
- SWF
1 stop7h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$498
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 junio 10, 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 junio 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
jue. 8/277:31 pm
SWF
- SJU
1 stop20h 27m
Multiple Airlines
dom. 8/306:00 am
SJU
- SWF
1 stop12h 41m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
dom. 8/210:28 am
SWF
- SJU
1 stop29h 37m
Multiple Airlines
mié. 8/56:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
dom. 8/1610:28 am
SWF
- SJU
1 stop29h 43m
Multiple Airlines
sáb. 8/226:00 am
SJU
- SWF
1 stop30h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
jue. 7/3010:28 am
SWF
- SJU
1 stop29h 37m
Multiple Airlines
mié. 8/56:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$357
This KAYAK deal was found by Cheapflights users on 6/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/212:05 pm
SWF
- NAS
2 stops20h 50m
Breeze Airways
vie. 9/119:20 am
NAS
- SWF
2 stops26h 19m
Breeze Airways
Deal found 6/5![Breeze Airways logo]()
$934
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
sáb. 7/412:05 pm
SWF
- SJU
2 stops12h 32m
Multiple Airlines
mié. 7/86:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
dom. 10/1111:53 am
SWF
- NAS
1 stop7h 22m
Multiple Airlines
mié. 10/144:00 pm
NAS
- SWF
1 stop17h 28m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
mié. 10/1412:39 pm
SWF
- NAS
2 stops20h 46m
Multiple Airlines
mié. 10/214:00 pm
NAS
- SWF
1 stop17h 48m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$500
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
sáb. 10/1012:39 pm
SWF
- NAS
2 stops20h 46m
Multiple Airlines
sáb. 10/174:00 pm
NAS
- SWF
1 stop19h 03m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$502
This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/112:05 pm
SWF
- NAS
2 stops20h 50m
Breeze Airways
vie. 8/79:55 am
NAS
- SWF
2 stops25h 30m
Breeze Airways
Deal found 6/7![Breeze Airways logo]()
$950
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
dom. 11/1512:00 pm
SWF
- NAS
1 stop7h 15m
Multiple Airlines
jue. 11/1911:30 am
NAS
- SWF
1 stop6h 28m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
sáb. 9/1912:39 pm
SWF
- PUJ
2 stops30h 11m
Multiple Airlines
dom. 9/2711:35 am
PUJ
- SWF
1 stop22h 56m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$504
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/1112:05 pm
SWF
- NAS
2 stops20h 50m
Breeze Airways
vie. 7/179:55 am
NAS
- SWF
2 stops25h 30m
Breeze Airways
Deal found 6/8![Breeze Airways logo]()
$990
This KAYAK deal was found by Cheapflights users on 6/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/812:05 pm
SWF
- NAS
2 stops20h 50m
Breeze Airways
vie. 8/149:55 am
NAS
- SWF
2 stops25h 30m
Breeze Airways
Deal found 6/6![Breeze Airways logo]()
$994
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
vie. 10/99:40 am
SWF
- PUJ
1 stop10h 45m
Multiple Airlines
vie. 10/161:10 pm
PUJ
- SWF
1 stop6h 48m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$515
This KAYAK deal was found by Cheapflights users on 6/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/1212:05 pm
SWF
- NAS
2 stops20h 50m
Breeze Airways
vie. 8/149:55 am
NAS
- SWF
2 stops25h 30m
Breeze Airways
Deal found 6/6![Breeze Airways logo]()
$994
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
dom. 8/1610:28 am
SWF
- PUJ
2 stops33h 51m
Multiple Airlines
dom. 8/2311:35 am
PUJ
- SWF
1 stop29h 14m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
lun. 8/3111:56 am
SWF
- PUJ
1 stop28h 44m
Multiple Airlines
dom. 9/611:35 am
PUJ
- SWF
1 stop23h 51m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
dom. 8/231:00 pm
SWF
- NAS
1 stop6h 15m
Multiple Airlines
jue. 8/2711:30 am
NAS
- SWF
1 stop7h 11m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$556
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
jue. 7/2310:28 am
SWF
- NAS
1 stop9h 02m
Multiple Airlines
mié. 7/294:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
dom. 7/1910:28 am
SWF
- NAS
1 stop8h 47m
Multiple Airlines
mié. 7/224:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
sáb. 7/46:44 pm
SWF
- PUJ
1 stop24h 06m
Multiple Airlines
mié. 7/83:31 pm
PUJ
- SWF
2 stops18h 07m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$624
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
jue. 8/610:33 am
SWF
- SJU
1 stop8h 59m
Multiple Airlines
lun. 8/103:10 am
SJU
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$670
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
mar. 7/2111:48 am
SWF
- SJU
1 stop7h 54m
Multiple Airlines
lun. 7/2710:48 pm
SJU
- SWF
1 stop12h 20m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$765
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
vie. 8/712:17 pm
SWF
- SJU
2 stops9h 26m
Multiple Airlines
sáb. 8/158:37 pm
SJU
- SWF
1 stop13h 16m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$773
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
mar. 8/1111:48 am
SWF
- SJU
1 stop14h 27m
Multiple Airlines
lun. 8/173:06 am
SJU
- SWF
1 stop8h 02m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$790
Last-minute flights from Stewart to CaribbeanDiscover last-minute flight deals from Stewart to Caribbean. Data last updated junio 10, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Caribbean. Data last updated junio 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
dom. 6/2810:28 am
SWF
- SJU
1 stop29h 30m
Multiple Airlines
vie. 7/36:45 pm
SJU
- SWF
2 stops38h 53m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
dom. 6/2810:28 am
SWF
- SJU
1 stop29h 30m
Multiple Airlines
mar. 7/75:45 pm
SJU
- SWF
2 stops39h 53m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$468
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
dom. 6/2810:28 am
SWF
- SJU
1 stop29h 30m
Multiple Airlines
mié. 7/16:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
jue. 7/211:45 am
SWF
- SJU
1 stop12h 52m
Multiple Airlines
mié. 7/85:15 pm
SJU
- SWF
2 stops16h 23m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
sáb. 7/412:05 pm
SWF
- SJU
2 stops12h 32m
Multiple Airlines
mié. 7/86:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
sáb. 7/46:44 pm
SWF
- SJU
1 stop13h 13m
Multiple Airlines
mar. 7/75:45 pm
SJU
- SWF
2 stops39h 53m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
sáb. 7/46:44 pm
SWF
- PUJ
1 stop24h 06m
Multiple Airlines
mié. 7/83:31 pm
PUJ
- SWF
2 stops18h 07m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$624
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
mié. 7/1512:05 pm
SWF
- PUJ
2 stops31h 06m
Multiple Airlines
vie. 7/241:10 pm
PUJ
- SWF
1 stop28h 44m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$654
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
dom. 7/1910:28 am
SWF
- NAS
1 stop8h 47m
Multiple Airlines
mié. 7/224:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
jue. 7/2310:28 am
SWF
- NAS
1 stop9h 02m
Multiple Airlines
mié. 7/294:00 pm
NAS
- SWF
1 stop17h 38m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
jue. 7/3011:45 am
SWF
- SJU
1 stop12h 56m
Multiple Airlines
mié. 8/56:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
jue. 7/3010:28 am
SWF
- SJU
1 stop29h 37m
Multiple Airlines
mar. 8/185:01 pm
SJU
- SWF
2 stops18h 24m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$398
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 junio 10, 2026.
Search for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Data last updated junio 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
jue. 9/37:30 pm
SWF
- SJU
1 stop20h 28m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
jue. 10/810:18 am
SWF
- SJU
1 stop13h 20m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
jue. 8/277:31 pm
SWF
- SJU
1 stop20h 27m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
jue. 8/201:00 pm
SWF
- SJU
1 stop26h 58m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
dom. 8/1610:28 am
SWF
- SJU
1 stop29h 43m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
dom. 10/411:48 am
SWF
- SJU
1 stop11h 50m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
mié. 8/2612:05 pm
SWF
- SJU
2 stops12h 18m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
jue. 10/1510:18 am
SWF
- NAS
1 stop24h 12m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
dom. 8/910:28 am
SWF
- SJU
1 stop29h 43m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
sáb. 8/2912:05 pm
SWF
- SJU
2 stops12h 18m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
dom. 11/1512:00 pm
SWF
- NAS
1 stop26h 50m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
mié. 8/2612:05 pm
SWF
- NAS
2 stops20h 50m
Breeze Airways
Deal found 6/6![Breeze Airways logo]()
$181
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 junio 10, 2026.
Round-trip from | $271 (Kiwi.com) |
|---|---|
One-way from | $134 (Kiwi.com) |
Popular in | May |
Cheapest in | October |
Average price | $347 |
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 junio 10, 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
jue. 8/27
7:31 pm-3:58 pm
1 stop20h 27m
San Juan Luis Munoz Marin Intl
dom. 8/30
6:00 am-6:41 pm
1 stop12h 41m
$295
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
dom. 8/2
10:28 am-4:05 pm
1 stop29h 37m
San Juan Luis Munoz Marin Intl
mié. 8/5
6:00 am-9:38 am
1 stop27h 38m
$325
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
dom. 8/16
10:28 am-4:11 pm
1 stop29h 43m
San Juan Luis Munoz Marin Intl
sáb. 8/22
6:00 am-12:10 pm
1 stop30h 10m
$339
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
jue. 7/30
10:28 am-4:05 pm
1 stop29h 37m
San Juan Luis Munoz Marin Intl
mié. 8/5
6:00 am-9:38 am
1 stop27h 38m
$357
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
sáb. 7/4
12:05 pm-12:37 am
2 stops12h 32m
San Juan Luis Munoz Marin Intl
mié. 7/8
6:00 am-9:38 am
1 stop27h 38m
$410
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
dom. 10/11
11:53 am-7:15 pm
1 stop7h 22m
Nassau Intl
mié. 10/14
4:00 pm-9:28 am
1 stop17h 28m
$438
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
mié. 10/14
12:39 pm-9:25 am
2 stops20h 46m
Nassau Intl
mié. 10/21
4:00 pm-9:48 am
1 stop17h 48m
$500
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
sáb. 10/10
12:39 pm-9:25 am
2 stops20h 46m
Nassau Intl
sáb. 10/17
4:00 pm-11:03 am
1 stop19h 03m
$502
New WindsorNassau
SWF - NAS
SWFNAS
New Windsor Stewart
dom. 11/15
12:00 pm-7:15 pm
1 stop7h 15m
Nassau Intl
jue. 11/19
11:30 am-5:58 pm
1 stop6h 28m
$504
New WindsorPunta Cana
SWF - PUJ
SWFPUJ
New Windsor Stewart
sáb. 9/19
12:39 pm-6:50 pm
2 stops30h 11m
Punta Cana
dom. 9/27
11:35 am-10:31 am
1 stop22h 56m
$504
Showing 1-10 of 56 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-PUJ
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-PUJ
No data available for this route at this time. Please check back soon.
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 junio 10, 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.
Overall
7.1
Food
6.6
Boarding
7.3
Comfort
7.5
Entertainment
7.2
Crew
7.9
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Overall
7.1
Food
6.6
Boarding
7.3
Comfort
7.5
Entertainment
7.2
Crew
7.9
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
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Stewart and Caribbean flights
Browse other Stewart and Caribbean flight options. Last updated on junio 10, 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 junio 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$345 | FlexibilityNo cancel fee | On-time62% |