$100+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Apr 9 — Apr 161
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 March 10, 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 March 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sat 6/135:56 pm
SJU
- SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:05 pm
SWF
- SJU
2 stops12h 24m
Multiple Airlines
Sat 5/235:56 pm
SJU
- SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sat 5/305:56 pm
SJU
- SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1711:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Thu 5/218:27 pm
SJU
- SWF
1 stop12h 24m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2110:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Tue 5/262:50 pm
SJU
- SWF
1 stop20h 35m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Sat 4/257:01 pm
SJU
- SWF
2 stops15h 54m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Fri 5/81:59 am
SJU
- SWF
2 stops9h 26m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sun 5/38:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sun 5/38:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Wed 4/292:38 am
BQN
- SWF
1 stop8h 30m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:41 am
SWF
- BQN
1 stop16h 22m
Multiple Airlines
Mon 5/252:58 am
BQN
- SWF
2 stops32h 27m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:15 pm
SWF
- BQN
2 stops13h 48m
Multiple Airlines
Mon 8/172:58 am
BQN
- SWF
1 stop8h 10m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$491
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 March 10, 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 March 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
SWF
- SJU
1 stop11h 47m
Multiple Airlines
Sat 8/2910:41 pm
SJU
- SWF
1 stop10h 17m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Tue 6/162:50 pm
SJU
- SWF
1 stop20h 35m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sat 8/85:56 pm
SJU
- SWF
1 stop15h 42m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2110:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Wed 5/278:27 pm
SJU
- SWF
1 stop12h 31m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Wed 7/83:23 pm
SJU
- SWF
1 stop18h 15m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sun 5/178:27 pm
SJU
- SWF
1 stop14h 28m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Wed 4/292:59 am
SJU
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Wed 4/292:38 am
BQN
- SWF
1 stop8h 30m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:41 am
SWF
- BQN
1 stop16h 22m
Multiple Airlines
Mon 5/252:58 am
BQN
- SWF
2 stops32h 27m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2210:29 am
SWF
- SJU
1 stop8h 26m
Multiple Airlines
Sun 3/294:34 pm
SJU
- SWF
1 stop16h 23m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$491
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sun 7/263:59 pm
SJU
- SWF
2 stops19h 36m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sat 5/22:59 am
SJU
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$519
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Sun 7/126:10 am
SJU
- SWF
2 stops11h 30m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:48 am
SWF
- SJU
1 stop14h 08m
Multiple Airlines
Tue 7/142:50 pm
SJU
- SWF
1 stop20h 35m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Sat 4/182:48 am
BQN
- SWF
1 stop8h 20m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Sat 5/22:48 am
BQN
- SWF
1 stop8h 20m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$641
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2211:48 am
SWF
- BQN
1 stop14h 09m
Multiple Airlines
Sat 3/282:42 am
BQN
- SWF
1 stop8h 26m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$651
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/210:29 am
SWF
- BQN
2 stops33h 50m
Multiple Airlines
Wed 4/82:43 am
BQN
- SWF
1 stop8h 25m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$655
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Sat 4/252:48 am
BQN
- SWF
1 stop8h 20m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$669
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2012:11 pm
SWF
- BQN
2 stops13h 31m
Multiple Airlines
Sat 3/212:42 am
BQN
- SWF
1 stop8h 26m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$725
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:48 am
SWF
- BQN
1 stop7h 54m
Multiple Airlines
Sat 4/112:43 am
BQN
- SWF
1 stop8h 25m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$775
Last-minute flights from Stewart to Puerto RicoDiscover last-minute flight deals from Stewart to Puerto Rico. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Puerto Rico. Data last updated March 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2211:48 am
SWF
- BQN
1 stop14h 09m
Multiple Airlines
Wed 3/252:42 am
BQN
- SWF
1 stop8h 26m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$565
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/210:29 am
SWF
- SJU
1 stop8h 26m
Multiple Airlines
Wed 4/87:54 pm
SJU
- SWF
1 stop15h 01m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/411:45 am
SWF
- BQN
1 stop14h 08m
Multiple Airlines
Wed 4/82:43 am
BQN
- SWF
1 stop8h 25m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$548
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sun 5/38:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sat 4/187:01 pm
SJU
- SWF
2 stops15h 54m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Sat 4/257:01 pm
SJU
- SWF
2 stops15h 54m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Wed 4/293:21 am
SJU
- SWF
1 stop7h 47m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:45 am
SWF
- BQN
1 stop13h 58m
Multiple Airlines
Wed 4/222:38 am
BQN
- SWF
1 stop8h 30m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$498
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Fri 5/81:59 am
SJU
- SWF
2 stops9h 26m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Sun 5/38:27 pm
SJU
- SWF
1 stop14h 23m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:48 am
SWF
- BQN
1 stop13h 55m
Multiple Airlines
Wed 4/292:38 am
BQN
- SWF
1 stop8h 30m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:45 am
SWF
- SJU
1 stop24h 38m
Multiple Airlines
Sat 5/22:59 am
SJU
- SWF
1 stop8h 09m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$414
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 March 10, 2026.
Search for one-way flight options from Stewart to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:45 am
SWF
- SJU
1 stop24h 48m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:45 am
SWF
- SJU
1 stop31h 10m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1011:45 am
SWF
- SJU
1 stop31h 37m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:45 am
SWF
- SJU
1 stop7h 37m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:28 am
SWF
- SJU
1 stop14h 19m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:11 pm
SWF
- BQN
2 stops13h 32m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2312:11 pm
SWF
- BQN
2 stops13h 31m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:05 pm
SWF
- BQN
2 stops13h 38m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:38 am
SWF
- BQN
1 stop16h 25m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:45 am
SWF
- BQN
1 stop13h 58m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:48 am
SWF
- BQN
1 stop7h 54m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$237
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 March 10, 2026.
Round-trip from | $264 (Kiwi.com) |
|---|---|
One-way from | $100 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $296 |
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 March 10, 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-12:47 am
1 stop11h 47m
San Juan Luis Munoz Marin Intl
Sat 8/29
10:41 pm-8:58 am
1 stop10h 17m
$363
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 6/11
10:28 am-12:47 am
1 stop14h 19m
San Juan Luis Munoz Marin Intl
Tue 6/16
2:50 pm-11:25 am
1 stop20h 35m
$383
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 7/30
10:28 am-12:47 am
1 stop14h 19m
San Juan Luis Munoz Marin Intl
Sat 8/8
5:56 pm-9:38 am
1 stop15h 42m
$383
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 5/21
10:28 am-12:47 am
1 stop14h 19m
San Juan Luis Munoz Marin Intl
Wed 5/27
8:27 pm-8:58 am
1 stop12h 31m
$411
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 7/5
10:28 am-12:47 am
1 stop14h 19m
San Juan Luis Munoz Marin Intl
Wed 7/8
3:23 pm-9:38 am
1 stop18h 15m
$414
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 5/14
11:45 am-7:22 pm
1 stop7h 37m
San Juan Luis Munoz Marin Intl
Sun 5/17
8:27 pm-10:55 am
1 stop14h 28m
$460
Quickest round-trip
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 4/23
11:45 am-7:22 pm
1 stop7h 37m
San Juan Luis Munoz Marin Intl
Wed 4/29
2:59 am-11:08 am
1 stop8h 09m
$465
New WindsorAguadilla
SWF - BQN
SWFBQN
New Windsor Stewart
Sun 4/26
11:48 am-1:43 am
1 stop13h 55m
Aguadilla Borinquen
Wed 4/29
2:38 am-11:08 am
1 stop8h 30m
$470
New WindsorAguadilla
SWF - BQN
SWFBQN
New Windsor Stewart
Fri 5/22
9:41 am-2:03 am
1 stop16h 22m
Aguadilla Borinquen
Mon 5/25
2:58 am-11:25 am
2 stops32h 27m
$479
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 3/22
10:29 am-6:55 pm
1 stop8h 26m
San Juan Luis Munoz Marin Intl
Sun 3/29
4:34 pm-8:57 am
1 stop16h 23m
$491
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
What is the cheapest month to book a flight from New Windsor to Puerto Rico?
Currently, March is the cheapest month in which you can book a flight from New Windsor to Puerto Rico (average of $62). Flying from New Windsor to Puerto Rico in August is currently the most expensive (average of $138). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 10, 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.
Overall
7.2
Boarding
7.4
Food
6.6
Crew
8.0
Comfort
7.5
Entertainment
7.2
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Overall
7.2
Boarding
7.4
Food
6.6
Crew
8.0
Comfort
7.5
Entertainment
7.2
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 March 10, 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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$336 | FlexibilityNo cancel fee | On-time62% |