$116+ Cheap flights from New Windsor (SWF) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Oct 10 — Oct 171
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Stewart to Caribbean
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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 September 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 September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/2511:58 am -
1 stop25h 33m
Sat 10/313:47 pm -
1 stop20h 21m
Deal found 9/8![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/2511:58 am -
1 stop25h 33m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 9/8![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/1811:53 am -
1 stop25h 38m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 9/6![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2910:38 am -
1 stop26h 08m
Wed 11/48:45 am -
1 stop26h 25m
Deal found 9/9![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/511:00 am -
1 stop25h 25m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 9/9![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1811:53 am -
1 stop25h 38m
Sat 10/243:20 pm -
1 stop19h 48m
Deal found 9/7![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/411:48 am -
1 stop25h 54m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/6![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/812:00 pm -
1 stop24h 25m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 9/7![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/1111:53 am -
1 stop25h 38m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/5![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1012:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/9![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/197:01 pm -
1 stop14h 56m
Thu 10/2210:52 am -
2 stops24h 44m
Deal found 9/8![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/7![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 September 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 September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/1111:53 am -
1 stop25h 38m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/6![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 11/97:04 pm -
1 stop14h 11m
Wed 11/113:59 pm -
2 stops19h 11m
Deal found 9/9![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops20h 39m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/7![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/1712:39 pm -
2 stops20h 39m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 9/8![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 11/812:00 pm -
1 stop24h 25m
Sat 11/143:20 pm -
1 stop20h 50m
Deal found 9/5![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Thu 10/1510:18 am -
1 stop27h 13m
Thu 10/225:11 pm -
2 stops42h 28m
Deal found 9/6![Multiple Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/2511:58 am -
1 stop25h 33m
Sun 11/111:20 am -
2 stops25h 16m
Deal found 9/6![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sat 11/712:39 pm -
2 stops20h 36m
Sat 11/143:20 pm -
1 stop20h 50m
Deal found 9/5![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/28:48 pm -
1 stop12h 47m
Tue 10/66:42 pm -
2 stops16h 57m
Deal found 9/9![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/810:18 am -
1 stop27h 13m
Wed 10/144:39 pm -
2 stops16h 49m
Deal found 9/7![Multiple Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Fri 10/28:48 pm -
1 stop12h 47m
Sun 10/42:57 am -
1 stop15h 26m
Deal found 9/5![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1012:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/9![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/7![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/2511:58 am -
1 stop26h 47m
Wed 10/284:00 pm -
1 stop17h 48m
Deal found 9/5![Multiple Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/2412:39 pm -
2 stops20h 46m
Wed 10/284:00 pm -
1 stop17h 48m
Deal found 9/10![Multiple Airlines logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/1012:39 pm -
2 stops20h 46m
Wed 10/144:00 pm -
1 stop17h 28m
Deal found 9/8![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/810:56 am -
1 stop23h 01m
Mon 10/1210:52 am -
2 stops48h 47m
Deal found 9/8![Multiple Airlines logo]()
$518
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/115:48 pm -
2 stops40h 09m
Sat 10/1711:17 am -
1 stop22h 59m
Deal found 9/8![Multiple Airlines logo]()
$523
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sat 9/1912:39 pm -
2 stops20h 46m
Wed 9/2312:00 pm -
1 stop22h 16m
Deal found 9/5![Multiple Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 12/136:49 pm -
2 stops18h 19m
Sat 1/161:45 pm -
1 stop20h 18m
Deal found 9/6![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops20h 46m
Wed 10/144:00 pm -
1 stop17h 28m
Deal found 9/7![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Wed 11/259:29 am -
1 stop16h 18m
Mon 11/302:54 pm -
2 stops45h 45m
Deal found 9/5![Multiple Airlines logo]()
$543
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Sat 9/1912:39 pm -
2 stops20h 46m
Thu 9/2412:00 pm -
1 stop22h 16m
Deal found 9/7![Multiple Airlines logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Wed 9/3012:39 pm -
2 stops20h 15m
Sun 10/412:35 pm -
1 stop29h 48m
Deal found 9/9![Multiple Airlines logo]()
$614
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Fri 11/2011:29 am -
1 stop7h 56m
Sun 11/2211:35 am -
1 stop24h 04m
Deal found 9/6![Multiple Airlines logo]()
$625
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Wed 10/2112:39 pm -
2 stops20h 15m
Sun 10/2512:35 pm -
1 stop29h 36m
Deal found 9/10![Multiple Airlines logo]()
$651
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Tue 2/168:11 pm -
1 stop16h 34m
Wed 2/241:45 pm -
2 stops19h 32m
Deal found 9/9![Multiple Airlines logo]()
$653
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 9/2511:06 am -
1 stop9h 19m
Fri 10/21:10 pm -
1 stop6h 48m
Deal found 9/9![Multiple Airlines logo]()
$697
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/99:40 am -
1 stop10h 45m
Fri 10/161:10 pm -
1 stop6h 48m
Deal found 9/8![Multiple Airlines logo]()
$711
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 9/2511:06 am -
1 stop9h 19m
Wed 9/301:59 pm -
2 stops20h 17m
Deal found 9/9![Multiple Airlines logo]()
$713
Last-minute flights from Stewart to CaribbeanDiscover last-minute flight deals from Stewart to Caribbean. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Caribbean. Data last updated September 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/411:48 am -
1 stop25h 54m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/6![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/7![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1012:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/9![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/1111:53 am -
1 stop25h 38m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/5![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/1811:53 am -
1 stop25h 38m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 9/6![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1811:53 am -
1 stop25h 38m
Sat 10/243:20 pm -
1 stop19h 48m
Deal found 9/7![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/197:01 pm -
1 stop14h 56m
Thu 10/2210:52 am -
2 stops24h 44m
Deal found 9/8![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/2412:39 pm -
2 stops20h 46m
Wed 10/284:00 pm -
1 stop17h 48m
Deal found 9/10![Multiple Airlines logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/2511:58 am -
1 stop25h 33m
Sat 10/313:47 pm -
1 stop20h 21m
Deal found 9/8![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/2511:58 am -
1 stop25h 33m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 9/8![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/2511:58 am -
1 stop26h 47m
Wed 10/284:00 pm -
1 stop17h 48m
Deal found 9/5![Multiple Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2910:38 am -
1 stop26h 08m
Wed 11/48:45 am -
1 stop26h 25m
Deal found 9/9![Multiple Airlines logo]()
$252
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 September 10, 2026.
Search for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/1512:00 pm -
1 stop24h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Sun 10/2511:58 am -
1 stop25h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 12/66:49 pm -
1 stop18h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$123
This Trip.com deal was found by Cheapflights users on 9/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1811:53 am -
1 stop25h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2910:38 am -
1 stop26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/511:00 am -
1 stop25h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/1211:00 am -
1 stop25h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/411:48 am -
1 stop25h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Mon 10/197:01 pm -
1 stop14h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 10/2511:58 am -
1 stop26h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/1512:00 pm -
2 stops27h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Wed 9/2312:39 pm -
2 stops21h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$171
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 September 10, 2026.
Round-trip from | $228 (Kiwi.com) |
|---|---|
One-way from | $116 (Kiwi.com) |
Popular in | July |
Cheapest in | October |
Average price | $285 |
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 7,457,451 searches. Data last updated September 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 New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sun 10/18
11:53 am-4:06 pm
2 stops28h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 12/9
12:39 pm-11:52 pm
2 stops10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 10/29
10:38 am-10:43 am
2 stops24h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$166
New WindsorNassau
SWF New Windsor Stewart - NAS Nassau Intl
SWFNAS
New Windsor Stewart
Thu 10/29
10:38 am-10:30 am
1 stop23h 52m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
New WindsorMontego Bay
SWF New Windsor Stewart - MBJ Montego Bay Sangster Intl
SWFMBJ
New Windsor Stewart
Sat 11/7
12:39 pm-3:29 pm
2 stops26h 50m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$187
New WindsorPunta Cana
SWF New Windsor Stewart - PUJ Punta Cana
SWFPUJ
New Windsor Stewart
Mon 10/26
7:01 pm-4:40 pm
1 stop21h 39m
Punta Cana
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$199
New WindsorNassau
SWF New Windsor Stewart - NAS Nassau Intl
SWFNAS
New Windsor Stewart
Wed 9/30
12:39 pm-9:25 am
2 stops20h 46m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 10/14
12:39 pm-2:09 am
3 stops13h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
New WindsorNassau
SWF New Windsor Stewart - NAS Nassau Intl
SWFNAS
New Windsor Stewart
Wed 10/28
12:39 pm-9:25 am
2 stops20h 46m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 10/21
12:39 pm-5:37 pm
2 stops28h 58m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$203
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-MBJ
SWF-PUJ
SWF-BQN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from New Windsor to Caribbean
SWF-0CB
SWF-SJU
SWF-NAS
SWF-MBJ
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 September 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.
Comfort
7.4
Crew
7.9
Boarding
7.3
Overall
7.1
Food
6.6
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
Comfort
7.4
Crew
7.9
Boarding
7.3
Overall
7.1
Food
6.6
Entertainment
7.2
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
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 September 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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% |