$113+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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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
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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 Puerto Rico
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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 July 2, 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 July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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
SWF
- SJU
1 stop11h 40m
Multiple Airlines
Sat 10/315:12 pm
SJU
- SWF
1 stop18h 56m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/231:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:58 pm
SWF
- BQN
1 stop15h 06m
Multiple Airlines
Tue 8/113:10 am
BQN
- SWF
1 stop15h 58m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1610:33 am
SWF
- BQN
1 stop15h 37m
Multiple Airlines
Tue 7/213:10 am
BQN
- SWF
1 stop15h 46m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/297:46 pm
SWF
- BQN
1 stop15h 18m
Multiple Airlines
Tue 8/43:10 am
BQN
- SWF
1 stop15h 58m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:58 pm
SWF
- BQN
1 stop15h 06m
Multiple Airlines
Fri 8/143:10 am
BQN
- SWF
1 stop12h 40m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1812:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 7/203:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/2111:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Mon 8/103:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$433
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 July 2, 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 July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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
SWF
- BQN
1 stop14h 53m
Multiple Airlines
Thu 11/123:48 am
BQN
- SWF
1 stop13h 52m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:18 am
SWF
- SJU
1 stop13h 20m
Multiple Airlines
Sun 10/182:58 am
SJU
- SWF
1 stop15h 13m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:48 am
SWF
- SJU
1 stop8h 04m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:48 am
SWF
- SJU
1 stop8h 04m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:48 am
SWF
- SJU
1 stop8h 04m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1610:33 am
SWF
- BQN
1 stop15h 37m
Multiple Airlines
Tue 7/213:10 am
BQN
- SWF
1 stop15h 46m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:48 am
SWF
- SJU
1 stop8h 04m
Multiple Airlines
Wed 9/25:37 pm
SJU
- SWF
1 stop16h 46m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1812:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 7/203:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1210:28 am
SWF
- SJU
1 stop29h 37m
Multiple Airlines
Wed 7/156:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 9/412:17 pm
SWF
- SJU
2 stops13h 58m
Multiple Airlines
Sun 9/66:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1611:45 am
SWF
- SJU
1 stop12h 56m
Multiple Airlines
Wed 7/225:15 pm
SJU
- SWF
2 stops16h 23m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Mon 8/243:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1411:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Mon 7/203:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/2212:05 pm
SWF
- SJU
2 stops12h 36m
Multiple Airlines
Sat 7/258:37 pm
SJU
- SWF
1 stop13h 16m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1812:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 7/273:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$485
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/2111:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Mon 7/273:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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
SWF
- BQN
1 stop23h 01m
Multiple Airlines
Sat 9/1910:52 am
BQN
- SWF
1 stop23h 24m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 8/210:33 am
SWF
- BQN
1 stop15h 37m
Multiple Airlines
Mon 8/33:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1512:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 7/203:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1411:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Sat 7/2512:19 pm
BQN
- SWF
1 stop21h 34m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1411:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Sat 7/1812:19 pm
BQN
- SWF
1 stop21h 34m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$567
Last-minute flights from Stewart to Puerto RicoDiscover last-minute flight deals from Stewart to Puerto Rico. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Puerto Rico. Data last updated July 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1112:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Tue 7/213:10 am
BQN
- SWF
1 stop15h 46m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1610:33 am
SWF
- BQN
1 stop15h 37m
Multiple Airlines
Tue 7/213:10 am
BQN
- SWF
1 stop15h 46m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1812:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Mon 7/203:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/297:46 pm
SWF
- BQN
1 stop15h 18m
Multiple Airlines
Tue 8/43:10 am
BQN
- SWF
1 stop15h 58m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:58 pm
SWF
- BQN
1 stop15h 06m
Multiple Airlines
Tue 8/113:10 am
BQN
- SWF
1 stop15h 58m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:58 pm
SWF
- BQN
1 stop15h 06m
Multiple Airlines
Fri 8/143:10 am
BQN
- SWF
1 stop12h 40m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/231:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- BQN
2 stops23h 04m
Multiple Airlines
Mon 8/313:10 am
BQN
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$266
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 July 2, 2026.
Search for one-way flight options from Stewart to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:30 pm
SWF
- SJU
1 stop20h 41m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/231:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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
SWF
- SJU
1 stop13h 10m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 9/67:30 pm
SWF
- SJU
1 stop20h 41m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1112:05 pm
SWF
- BQN
2 stops22h 59m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/2012:17 pm
SWF
- BQN
2 stops13h 53m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1512:05 pm
SWF
- BQN
2 stops38h 05m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 7/1411:48 am
SWF
- BQN
1 stop14h 22m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$240
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 July 2, 2026.
Round-trip from | $250 (Kiwi.com) |
|---|---|
One-way from | $113 (Kiwi.com) |
Popular in | May |
Cheapest in | October |
Average price | $351 |
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 2,558,603 searches. Data last updated July 2, 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 - SJU
SWFSJU
New Windsor Stewart
Thu 8/20
1:00 pm-4:11 pm
1 stop27h 11m
San Juan Luis Munoz Marin Intl
Tue 9/1
5:37 pm-11:25 am
2 stops17h 48m
$268
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 8/26
12:05 pm-12:56 am
2 stops12h 51m
San Juan Luis Munoz Marin Intl
Sun 8/30
6:35 am-6:41 pm
1 stop12h 06m
$270
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 8/22
12:05 pm-12:56 am
2 stops12h 51m
San Juan Luis Munoz Marin Intl
Sun 8/30
6:35 am-6:41 pm
1 stop12h 06m
$318
New WindsorAguadilla
SWF - BQN
SWFBQN
New Windsor Stewart
Mon 11/9
7:04 pm-10:57 am
1 stop14h 53m
Aguadilla Borinquen
Thu 11/12
3:48 am-4:40 pm
1 stop13h 52m
$360
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 10/15
10:18 am-11:38 pm
1 stop13h 20m
San Juan Luis Munoz Marin Intl
Sun 10/18
2:58 am-6:11 pm
1 stop15h 13m
$365
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 8/25
11:48 am-7:52 pm
1 stop8h 04m
San Juan Luis Munoz Marin Intl
Tue 9/1
5:37 pm-11:25 am
2 stops17h 48m
$370
Quickest round-trip
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 8/25
11:48 am-7:52 pm
1 stop8h 04m
San Juan Luis Munoz Marin Intl
Thu 9/3
6:35 am-6:40 pm
1 stop12h 05m
$373
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 8/25
11:48 am-7:52 pm
1 stop8h 04m
San Juan Luis Munoz Marin Intl
Sun 8/30
6:35 am-6:41 pm
1 stop12h 06m
$383
New WindsorAguadilla
SWF - BQN
SWFBQN
New Windsor Stewart
Thu 7/16
10:33 am-2:10 am
1 stop15h 37m
Aguadilla Borinquen
Tue 7/21
3:10 am-6:56 pm
1 stop15h 46m
$388
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 8/25
11:48 am-7:52 pm
1 stop8h 04m
San Juan Luis Munoz Marin Intl
Wed 9/2
5:37 pm-10:23 am
1 stop16h 46m
$412
Showing 1-10 of 43 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.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated July 2, 2026.
Get a feel of what it's like to fly with JetBlue from New Windsor to Puerto Rico by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.6
Crew
7.9
Entertainment
7.2
Overall
7.1
Boarding
7.3
Comfort
7.5
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Food
6.6
Crew
7.9
Entertainment
7.2
Overall
7.1
Boarding
7.3
Comfort
7.5
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Related info for your journey
Find useful and relevant information for your journey from Stewart to Puerto Rico. 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 Puerto Rico
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Complete your trip
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Stewart and Puerto Rico flights
Browse other Stewart and Puerto Rico flight options. Last updated on July 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Stewart to Puerto Rico
Discover the top airline that operate flights from Stewart to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% |