$107+ Cheap flights from New Windsor (SWF) to Puerto Rico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Sep 24 — Oct 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 Puerto Rico 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 Puerto Rico
Cheapest
Best
Last-minute
One-way
Cheapest flights from Stewart to Puerto RicoExplore the most affordable flight options available from Stewart to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 25, 2026.
Explore the most affordable flight options available from Stewart to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 8/25![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 10/110:28 am -
1 stop27h 06m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 8/23![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:18 am -
1 stop27h 13m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 8/21![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2511:58 am -
1 stop25h 33m
Sat 10/313:20 pm -
1 stop20h 48m
Deal found 8/23![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/110:28 am -
1 stop27h 06m
Wed 10/78:45 am -
1 stop24h 43m
Deal found 8/22![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1111:53 am -
1 stop25h 38m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 8/21![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/2210:38 am -
1 stop26h 53m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 8/22![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:48 am -
1 stop25h 46m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 8/23![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 10/2910:38 am -
1 stop26h 50m
Sat 10/313:20 pm -
1 stop20h 48m
Deal found 8/23![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Mon 10/267:01 pm -
1 stop14h 14m
Mon 11/27:23 am -
1 stop11h 48m
Deal found 8/24![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:36 am -
1 stop15h 34m
Sun 9/1311:08 am -
1 stop23h 23m
Deal found 8/22![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 11/2011:29 am -
1 stop30h 03m
Tue 12/15:08 pm -
2 stops19h 31m
Deal found 8/21![Multiple Airlines logo]()
$439
Best flights from Stewart to Puerto RicoDiscover carefully curated flight deals from Stewart to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 25, 2026.
Discover carefully curated flight deals from Stewart to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:06 am -
1 stop12h 07m
Sat 9/196:10 pm -
1 stop16h 13m
Deal found 8/21![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/21. 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
Mon 11/234:18 pm -
1 stop18h 51m
Deal found 8/21![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 11/511:00 am -
1 stop25h 25m
Mon 11/97:23 am -
1 stop11h 51m
Deal found 8/22![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:30 pm -
1 stop15h 45m
Tue 11/172:18 pm -
2 stops22h 21m
Deal found 8/23![Multiple Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 11/511:00 am -
1 stop25h 25m
Sun 11/87:26 pm -
1 stop23h 48m
Deal found 8/20![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/1212:39 pm -
2 stops20h 56m
Wed 9/166:42 pm -
1 stop15h 34m
Deal found 8/23![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:30 pm -
1 stop20h 13m
Mon 11/97:23 am -
1 stop11h 51m
Deal found 8/22![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:36 am -
1 stop15h 34m
Sun 9/1311:08 am -
1 stop23h 23m
Deal found 8/22![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/1710:56 am -
1 stop12h 17m
Sun 9/203:55 pm -
1 stop18h 36m
Deal found 8/21![Multiple Airlines logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 11/412:39 pm -
2 stops11h 20m
Thu 11/53:55 am -
1 stop13h 45m
Deal found 8/20![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/912:39 pm -
2 stops13h 13m
Wed 9/166:42 pm -
1 stop15h 34m
Deal found 8/20![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:56 am -
1 stop12h 17m
Sat 9/129:50 pm -
1 stop12h 26m
Deal found 8/23![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/2410:56 am -
1 stop23h 17m
Sun 10/411:08 am -
2 stops24h 28m
Deal found 8/22![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:33 am -
1 stop15h 37m
Wed 9/162:44 am -
1 stop7h 32m
Deal found 8/25![Multiple Airlines logo]()
$514
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 12/237:46 pm -
1 stop19h 27m
Wed 12/303:47 am -
1 stop7h 39m
Deal found 8/22![Multiple Airlines logo]()
$862
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 12/2411:06 am -
1 stop28h 07m
Wed 12/303:47 am -
1 stop7h 39m
Deal found 8/23![Multiple Airlines logo]()
$868
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 12/218:50 pm -
1 stop18h 23m
Thu 12/313:47 am -
2 stops8h 49m
Deal found 8/25![Multiple Airlines logo]()
$1,039
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 12/2411:06 am -
1 stop28h 07m
Sun 1/35:08 pm -
2 stops19h 28m
Deal found 8/23![Multiple Airlines logo]()
$1,079
Last-minute flights from Stewart to Puerto RicoDiscover last-minute flight deals from Stewart to Puerto Rico. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Puerto Rico. Data last updated August 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3111:56 am -
1 stop14h 14m
Wed 9/911:12 am -
1 stop23h 04m
Deal found 8/20![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:36 am -
1 stop15h 34m
Sun 9/1311:08 am -
1 stop23h 23m
Deal found 8/22![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:06 am -
1 stop12h 07m
Thu 9/173:55 pm -
1 stop18h 21m
Deal found 8/21![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:06 am -
1 stop12h 07m
Sat 9/196:10 pm -
1 stop16h 13m
Deal found 8/21![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:06 am -
1 stop12h 07m
Wed 9/166:42 pm -
1 stop15h 34m
Deal found 8/21![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:06 am -
1 stop12h 07m
Fri 9/184:39 pm -
2 stops19h 00m
Deal found 8/20![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:06 am -
1 stop12h 07m
Sun 9/136:42 pm -
1 stop15h 49m
Deal found 8/20![Multiple Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/1212:39 pm -
2 stops20h 56m
Wed 9/166:42 pm -
1 stop15h 34m
Deal found 8/23![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/1411:21 am -
1 stop22h 14m
Sat 9/196:10 pm -
1 stop16h 13m
Deal found 8/21![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/1710:56 am -
1 stop12h 17m
Wed 9/234:39 pm -
1 stop17h 44m
Deal found 8/21![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/2410:56 am -
1 stop23h 17m
Sun 10/411:08 am -
2 stops24h 28m
Deal found 8/22![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 9/2612:39 pm -
2 stops13h 13m
Wed 9/308:45 am -
1 stop24h 53m
Deal found 8/25![Multiple Airlines logo]()
$306
One-way flights from Stewart to Puerto RicoSearch for one-way flight options from Stewart to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
Search for one-way flight options from Stewart to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/2511:58 am -
1 stop25h 33m
Deal found 8/24![Multiple Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:48 am -
1 stop25h 46m
Deal found 8/21![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1811:53 am -
1 stop25h 38m
Deal found 8/23![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:00 pm -
1 stop24h 25m
Deal found 8/21![Multiple Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/1510:18 am -
1 stop27h 13m
Deal found 8/22![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:31 pm -
1 stop20h 40m
Deal found 8/21![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/2910:38 am -
1 stop26h 50m
Deal found 8/24![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 11/1211:00 am -
1 stop25h 25m
Deal found 8/20![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:48 pm -
1 stop13h 26m
Deal found 8/22![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/3012:39 pm -
2 stops45h 34m
Deal found 8/22![Multiple Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/110:56 am -
1 stop23h 17m
Deal found 8/22![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:33 am -
1 stop15h 37m
Deal found 8/21![Multiple Airlines logo]()
$211
Find flight deals from Stewart to Puerto Rico
Keep the following information in mind while searching for Stewart to Puerto Rico flight deals. Data was last updated August 25, 2026.
Round-trip from | $193 (Kiwi.com) |
|---|---|
One-way from | $107 (Kiwi.com) |
Popular in | July |
Cheapest in | October |
Average price | $376 |
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart to Puerto Rico 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 August 25, 2026.
Use the filters below to find and compare flights from New Windsor to Puerto Rico 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
Fri 9/11
11:06 am-11:13 pm
1 stop12h 07m
San Juan Luis Munoz Marin Intl
Sat 9/19
6:10 pm-10:23 am
1 stop16h 13m
$266
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Mon 11/16
7:04 pm-10:15 am
1 stop14h 11m
San Juan Luis Munoz Marin Intl
Mon 11/23
4:18 pm-10:09 am
1 stop18h 51m
$281
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 11/5
11:00 am-1:25 pm
1 stop25h 25m
San Juan Luis Munoz Marin Intl
Mon 11/9
7:23 am-6:14 pm
1 stop11h 51m
$290
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Fri 11/13
5:30 pm-10:15 am
1 stop15h 45m
San Juan Luis Munoz Marin Intl
Tue 11/17
2:18 pm-11:39 am
2 stops22h 21m
$336
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 11/5
11:00 am-1:25 pm
1 stop25h 25m
San Juan Luis Munoz Marin Intl
Sun 11/8
7:26 pm-6:14 pm
1 stop23h 48m
$350
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 9/12
12:39 pm-9:35 am
2 stops20h 56m
San Juan Luis Munoz Marin Intl
Wed 9/16
6:42 pm-10:16 am
1 stop15h 34m
$356
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Fri 11/6
5:30 pm-2:43 pm
1 stop20h 13m
San Juan Luis Munoz Marin Intl
Mon 11/9
7:23 am-6:14 pm
1 stop11h 51m
$357
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Fri 9/4
10:36 am-2:10 am
1 stop15h 34m
Aguadilla Borinquen
Sun 9/13
11:08 am-10:31 am
1 stop23h 23m
$363
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 9/17
10:56 am-11:13 pm
1 stop12h 17m
San Juan Luis Munoz Marin Intl
Sun 9/20
3:55 pm-10:31 am
1 stop18h 36m
$384
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 11/4
12:39 pm-12:59 am
2 stops11h 20m
San Juan Luis Munoz Marin Intl
Thu 11/5
3:55 am-4:40 pm
1 stop13h 45m
$390
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Stewart to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Stewart with our price prediction graph.
SWF-SJU
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 Puerto Rico
SWF-PR0
SWF-SJU
SWF-BQN
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Stewart to Puerto Rico. 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