$121+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Nov 24 — Dec 11
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 October 25, 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 October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 11/226:48 pm -
1 stop18h 11m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 10/24![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 12/106:49 pm -
1 stop24h 48m
Wed 12/166:25 am -
1 stop29h 52m
Deal found 10/24![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1612:39 pm -
2 stops22h 58m
Mon 12/216:00 am -
1 stop28h 45m
Deal found 10/23![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
2 stops24h 35m
Sun 12/62:54 pm -
1 stop20h 19m
Deal found 10/22![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:39 pm -
2 stops30h 58m
Thu 12/106:25 am -
1 stop12h 34m
Deal found 10/23![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 12/912:39 pm -
2 stops30h 58m
Wed 12/166:25 am -
1 stop29h 52m
Deal found 10/20![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 stops21h 16m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 10/24![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 12/1212:39 pm -
2 stops26h 14m
Wed 12/237:25 am -
1 stop28h 52m
Deal found 10/20![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1512:00 pm -
1 stop24h 25m
Thu 11/197:00 am -
1 stop11h 58m
Deal found 10/20![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 12/1212:39 pm -
2 stops26h 14m
Mon 12/216:00 am -
1 stop28h 45m
Deal found 10/20![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:39 pm -
2 stops13h 13m
Wed 12/93:47 am -
1 stop7h 39m
Deal found 10/23![Multiple Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Mon 11/167:04 pm -
1 stop14h 48m
Sat 11/213:47 am -
1 stop7h 29m
Deal found 10/23![Multiple Airlines logo]()
$391
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 October 25, 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 October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 stops21h 16m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 10/24![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 1/612:39 pm -
1 stop10h 53m
Tue 1/1210:53 pm -
2 stops13h 46m
Deal found 10/20![Multiple Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:49 pm -
1 stop24h 48m
Sun 12/138:44 pm -
1 stop14h 29m
Deal found 10/20![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
2 stops24h 35m
Wed 12/93:47 am -
1 stop7h 39m
Deal found 10/23![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 12/912:39 pm -
2 stops13h 13m
Sat 12/123:47 am -
1 stop7h 39m
Deal found 10/24![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 1/2112:25 pm -
1 stop23h 12m
Thu 1/287:41 pm -
2 stops16h 16m
Deal found 10/22![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2012:39 pm -
2 stops12h 32m
Wed 1/2710:53 pm -
1 stop12h 23m
Deal found 10/22![Multiple Airlines logo]()
$427
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/1311:06 am -
1 stop14h 46m
Sat 12/192:44 pm -
1 stop20h 42m
Deal found 10/22![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/1311:06 am -
1 stop14h 46m
Thu 12/173:13 am -
2 stops9h 23m
Deal found 10/22![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/312:39 pm -
2 stops12h 32m
Wed 3/106:00 am -
1 stop28h 24m
Deal found 10/23![Multiple Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:56 am -
1 stop14h 51m
Tue 11/243:47 am -
1 stop7h 39m
Deal found 10/20![Multiple Airlines logo]()
$472
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 12/1712:07 pm -
1 stop11h 07m
Wed 12/306:00 am -
1 stop30h 17m
Deal found 10/24![Multiple Airlines logo]()
$502
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:06 am -
1 stop14h 46m
Thu 12/173:13 am -
2 stops9h 23m
Deal found 10/20![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 2/76:47 pm -
2 stops31h 17m
Fri 2/123:59 am -
1 stop15h 45m
Deal found 10/20![Multiple Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/411:03 am -
1 stop14h 42m
Sun 12/63:47 am -
2 stops8h 49m
Deal found 10/21![Multiple Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/2012:07 pm -
1 stop11h 07m
Mon 12/287:25 am -
1 stop27h 20m
Deal found 10/22![Multiple Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 1/1410:53 am -
1 stop12h 36m
Tue 1/1910:53 pm -
2 stops13h 46m
Deal found 10/21![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 12/1712:07 pm -
1 stop11h 07m
Wed 1/611:16 pm -
1 stop12h 00m
Deal found 10/24![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
2 stops13h 06m
Wed 12/303:13 am -
1 stop8h 13m
Deal found 10/22![Multiple Airlines logo]()
$521
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/311:06 am -
1 stop14h 39m
Sun 12/63:47 am -
2 stops8h 49m
Deal found 10/21![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/311:06 am -
1 stop14h 39m
Thu 12/102:54 pm -
2 stops21h 42m
Deal found 10/23![Multiple Airlines logo]()
$538
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:39 pm -
2 stops27h 21m
Wed 1/1310:00 am -
1 stop25h 35m
Deal found 10/23![Multiple Airlines logo]()
$869
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/66:49 pm -
1 stop21h 11m
Sun 12/1310:00 am -
1 stop7h 59m
Deal found 10/22![Multiple Airlines logo]()
$900
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Mon 1/2511:58 am -
2 stops28h 02m
Sat 2/610:00 am -
1 stop25h 39m
Deal found 10/21![Multiple Airlines logo]()
$921
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:39 pm -
2 stops27h 21m
Thu 12/1010:00 am -
1 stop7h 59m
Deal found 10/23![Multiple Airlines logo]()
$925
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 stop29h 00m
Thu 11/1910:00 am -
1 stop7h 58m
Deal found 10/24![Multiple Airlines logo]()
$1,005
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 12/2412:07 pm -
1 stop27h 53m
Sun 1/1010:00 am -
1 stop9h 11m
Deal found 10/24![Multiple Airlines logo]()
$1,278
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 12/2312:39 pm -
2 stops27h 21m
Sat 1/210:00 am -
1 stop25h 17m
Deal found 10/24![Multiple Airlines logo]()
$1,436
Last-minute flights from Stewart to CaribbeanDiscover last-minute flight deals from Stewart to Caribbean. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Caribbean. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 10/267:01 pm -
1 stop14h 51m
Fri 10/3011:37 am -
2 stops24h 02m
Deal found 10/20![Multiple Airlines logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 stops21h 16m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 10/24![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/812:00 pm -
1 stop24h 25m
Fri 11/207:31 am -
2 stops29h 08m
Deal found 10/20![Multiple Airlines logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Mon 11/97:04 pm -
1 stop14h 11m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 10/23![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/1210:56 am -
1 stop23h 36m
Mon 11/1612:37 pm -
2 stops48h 02m
Deal found 10/21![Multiple Airlines logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1512:00 pm -
1 stop24h 25m
Thu 11/197:00 am -
1 stop11h 58m
Deal found 10/20![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Mon 11/167:04 pm -
1 stop14h 48m
Sat 11/213:47 am -
1 stop7h 29m
Deal found 10/23![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Mon 11/167:04 pm -
1 stop14h 11m
Thu 11/197:00 am -
1 stop11h 58m
Deal found 10/21![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:39 pm -
2 stops21h 13m
Sat 11/213:47 am -
1 stop7h 29m
Deal found 10/23![Multiple Airlines logo]()
$427
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:56 am -
1 stop14h 51m
Tue 11/243:47 am -
1 stop7h 39m
Deal found 10/20![Multiple Airlines logo]()
$472
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 11/226:48 pm -
1 stop18h 11m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 10/24![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/226:48 pm -
1 stop18h 11m
Mon 11/302:59 am -
2 stops33h 40m
Deal found 10/22![Multiple Airlines logo]()
$387
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 October 25, 2026.
Search for one-way flight options from Stewart to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 1/612:39 pm -
1 stop10h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/1512:00 pm -
1 stop24h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 1/108:01 pm -
1 stop23h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 1/3112:25 pm -
1 stop23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:39 pm -
2 stops30h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/167:04 pm -
3 stops38h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/66:49 pm -
2 stops53h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 1/3012:39 pm -
2 stops21h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/1612:39 pm -
2 stops21h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/1910:56 am -
1 stop14h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:39 pm -
2 stops37h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Mon 11/2311:29 am -
1 stop14h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$204
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 October 25, 2026.
Round-trip from | $258 (Kiwi.com) |
|---|---|
One-way from | $121 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $337 |
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 October 25, 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
Wed 1/20
12:39 pm-2:11 am
3 stops36h 32m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sun 12/6
6:49 pm-8:37 pm
1 stop24h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Sat 12/12
12:39 pm-2:52 am
2 stops37h 13m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 12/12
12:39 pm-1:07 am
2 stops35h 28m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$211
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Mon 11/9
12:16 pm-10:52 am
2 stops21h 36m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$234
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Mon 11/2
5:46 pm-3:19 pm
2 stops44h 33m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$253
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sun 1/3
12:07 pm-12:37 pm
1 stop23h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$255
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 10/31
12:39 pm-11:28 pm
3 stops34h 49m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$259
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 11/4
12:39 pm-1:25 pm
3 stops23h 46m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$261
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 12/5
12:39 pm-2:59 pm
3 stops25h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$262
Showing 1-10 of 55 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-BQN
SWF-CAP
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-BQN
SWF-CAP
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 October 25, 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.
Boarding
7.3
Overall
7.1
Comfort
7.4
Entertainment
7.1
Crew
7.9
Food
6.6
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
Boarding
7.3
Overall
7.1
Comfort
7.4
Entertainment
7.1
Crew
7.9
Food
6.6
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
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 October 25, 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 October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% |