$125+ Cheap flights from New Windsor (SWF) to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Dec 3 — Dec 101
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 November 3, 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 November 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/106:49 pm -
1 stop24h 48m
Wed 12/166:25 am -
1 stop29h 52m
Deal found 10/30![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:48 pm -
1 stop18h 11m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 10/31![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/66:49 pm -
1 stop24h 48m
Thu 12/106:25 am -
1 stop12h 34m
Deal found 11/2![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Wed 11/1812:39 pm -
2 stops11h 20m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 11/2![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:49 pm -
1 stop24h 48m
Tue 12/159:52 pm -
2 stops38h 25m
Deal found 10/31![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:48 pm -
1 stop18h 11m
Fri 12/44:07 pm -
2 stops20h 32m
Deal found 10/31![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Tue 11/2410:59 am -
1 stop26h 00m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 11/2![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/512:39 pm -
2 stops47h 50m
Sun 12/136:25 am -
1 stop12h 34m
Deal found 10/29![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/106:49 pm -
1 stop24h 48m
Sun 12/136:25 am -
1 stop12h 34m
Deal found 10/30![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
2 stops24h 35m
Sun 12/62:54 pm -
1 stop20h 19m
Deal found 11/3![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 11/1412:39 pm -
2 stops21h 13m
Wed 11/1812:22 pm -
1 stop22h 54m
Deal found 10/30![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 12/412:16 pm -
2 stops13h 29m
Sun 12/62:54 pm -
1 stop20h 19m
Deal found 11/2![Multiple Airlines logo]()
$454
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 November 3, 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 November 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 1/2112:25 pm -
1 stop23h 12m
Wed 1/276:00 am -
1 stop30h 35m
Deal found 11/2![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/612:39 pm -
1 stop10h 53m
Tue 1/123:48 pm -
2 stops20h 51m
Deal found 10/31![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 1/612:39 pm -
2 stops12h 03m
Sat 1/165:02 pm -
1 stop18h 01m
Deal found 11/1![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/106:49 pm -
1 stop24h 48m
Sun 12/136:25 am -
1 stop12h 34m
Deal found 10/30![Multiple Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:39 pm -
2 stops12h 34m
Sun 12/136:25 am -
1 stop12h 34m
Deal found 11/3![Multiple Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/912:39 pm -
1 stop10h 53m
Sun 1/2410:53 pm -
2 stops13h 04m
Deal found 10/31![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Fri 1/811:58 am -
2 stops11h 40m
Sat 1/1610:53 pm -
1 stop12h 23m
Deal found 11/1![Multiple Airlines logo]()
$502
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 1/811:58 am -
2 stops11h 40m
Sun 1/106:27 am -
1 stop13h 44m
Deal found 10/31![Multiple Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 11/2011:29 am -
1 stop14h 18m
Sat 11/213:47 am -
1 stop7h 29m
Deal found 11/2![Multiple Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:06 am -
1 stop14h 39m
Sat 12/53:47 am -
1 stop7h 39m
Deal found 10/31![Multiple Airlines logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 3/410:14 am -
1 stop25h 23m
Sun 3/710:53 pm -
1 stop12h 04m
Deal found 11/3![Multiple Airlines logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:16 pm -
2 stops13h 29m
Sat 12/53:47 am -
1 stop7h 39m
Deal found 10/31![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 1/212:39 pm -
1 stop10h 53m
Thu 1/711:26 pm -
2 stops12h 31m
Deal found 11/2![Multiple Airlines logo]()
$600
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Tue 12/2210:35 am -
1 stop25h 02m
Wed 1/611:16 pm -
1 stop12h 00m
Deal found 10/30![Multiple Airlines logo]()
$624
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 3/127:52 pm -
1 stop17h 08m
Sun 3/143:59 am -
1 stop15h 03m
Deal found 11/3![Multiple Airlines logo]()
$637
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Thu 2/1110:56 am -
1 stop15h 08m
Thu 2/182:55 pm -
1 stop20h 04m
Deal found 11/1![Multiple Airlines logo]()
$660
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Wed 11/2511:06 am -
1 stop14h 41m
Mon 11/302:54 pm -
2 stops45h 45m
Deal found 11/2![Multiple Airlines logo]()
$663
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1112:16 pm -
2 stops13h 36m
Sat 12/123:47 am -
1 stop7h 39m
Deal found 10/31![Multiple Airlines logo]()
$685
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/298:36 am -
1 stop28h 23m
Sat 12/53:47 am -
1 stop7h 39m
Deal found 10/30![Multiple Airlines logo]()
$714
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/1711:06 am -
1 stop13h 37m
Sat 12/263:13 am -
1 stop8h 13m
Deal found 11/2![Multiple Airlines logo]()
$726
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/2411:06 am -
1 stop13h 37m
Wed 12/302:44 pm -
1 stop20h 42m
Deal found 11/2![Multiple Airlines logo]()
$762
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/2411:06 am -
1 stop13h 37m
Wed 12/303:13 am -
1 stop8h 13m
Deal found 11/2![Multiple Airlines logo]()
$767
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/237:46 pm -
1 stop28h 57m
Mon 12/283:13 am -
1 stop17h 32m
Deal found 10/30![Multiple Airlines logo]()
$781
Last-minute flights from Stewart to Puerto RicoDiscover last-minute flight deals from Stewart to Puerto Rico. Data last updated November 3, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Puerto Rico. Data last updated November 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 11/1412:39 pm -
2 stops21h 13m
Wed 11/1812:22 pm -
1 stop22h 54m
Deal found 10/30![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Wed 11/1812:39 pm -
2 stops11h 20m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 11/2![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:48 pm -
1 stop18h 11m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 10/31![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:48 pm -
1 stop18h 11m
Fri 12/44:07 pm -
2 stops20h 32m
Deal found 10/31![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Tue 11/2410:59 am -
1 stop26h 00m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 11/2![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
2 stops24h 35m
Sun 12/62:54 pm -
1 stop20h 19m
Deal found 11/3![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 12/412:16 pm -
2 stops13h 29m
Sun 12/62:54 pm -
1 stop20h 19m
Deal found 11/2![Multiple Airlines logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/512:39 pm -
2 stops47h 50m
Sun 12/136:25 am -
1 stop12h 34m
Deal found 10/29![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/66:49 pm -
1 stop24h 48m
Thu 12/106:25 am -
1 stop12h 34m
Deal found 11/2![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/106:49 pm -
1 stop24h 48m
Wed 12/166:25 am -
1 stop29h 52m
Deal found 10/30![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:49 pm -
1 stop24h 48m
Tue 12/159:52 pm -
2 stops38h 25m
Deal found 10/31![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/106:49 pm -
1 stop24h 48m
Sun 12/136:25 am -
1 stop12h 34m
Deal found 10/30![Multiple Airlines logo]()
$385
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 November 3, 2026.
Search for one-way flight options from Stewart to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated November 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:49 pm -
1 stop24h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sun 1/1712:25 pm -
1 stop23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 1/3112:25 pm -
1 stop23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 1/2712:39 pm -
2 stops37h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:39 pm -
2 stops47h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:49 pm -
1 stop24h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$147
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2210:49 am -
1 stop15h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/1412:39 pm -
2 stops21h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/1910:56 am -
1 stop14h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$189
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:03 am -
1 stop14h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 2/2110:56 am -
1 stop26h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/1112:39 pm -
2 stops21h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![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 November 3, 2026.
Round-trip from | $259 (Kiwi.com) |
|---|---|
One-way from | $125 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $386 |
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 November 3, 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
Thu 12/10
6:49 pm-8:37 pm
1 stop24h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$152
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Mon 2/22
10:49 am-3:04 am
1 stop15h 15m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 1/16
12:39 pm-12:37 pm
2 stops22h 58m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Sat 11/14
12:39 pm-10:52 am
2 stops21h 13m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Thu 11/19
10:56 am-1:59 pm
1 stop26h 03m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$196
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sun 11/22
6:48 pm-6:13 am
2 stops34h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 12/3
6:49 pm-8:45 pm
1 stop24h 56m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$207
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sun 12/13
6:49 pm-8:37 pm
1 stop24h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Wed 2/24
12:39 pm-2:00 pm
2 stops24h 21m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$232
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Tue 11/24
10:59 am-1:36 am
2 stops37h 37m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$238
Showing 1-10 of 41 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 November 3, 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.
Entertainment
7.2
Overall
7.1
Crew
7.9
Comfort
7.4
Boarding
7.3
Food
6.6
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
Entertainment
7.2
Overall
7.1
Crew
7.9
Comfort
7.4
Boarding
7.3
Food
6.6
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
Related info for your journey
Find useful and relevant information for your journey from Stewart to 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 November 3, 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 7,457,451 searches. Data last updated November 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% |