$117+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Oct 8 — Oct 151
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 September 8, 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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/2511:58 am -
1 stop25h 33m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 9/6![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/1811:53 am -
1 stop25h 38m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 9/5![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:48 am -
1 stop25h 54m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/4![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1811:53 am -
1 stop25h 38m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 9/3![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/812:00 pm -
1 stop24h 25m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 9/3![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1811:53 am -
1 stop25h 38m
Sat 10/243:20 pm -
1 stop19h 48m
Deal found 9/7![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/1111:53 am -
1 stop25h 38m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/5![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2312:39 pm -
2 stops21h 34m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 9/2612:39 pm -
2 stops21h 34m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2510:48 am -
2 stops23h 26m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2312:39 pm -
2 stops21h 34m
Sat 9/2611:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/7![Multiple Airlines logo]()
$399
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 September 8, 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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1811:53 am -
1 stop25h 38m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 9/3![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1111:53 am -
1 stop25h 38m
Sat 10/173:20 pm -
1 stop19h 43m
Deal found 9/4![Multiple Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops20h 39m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/7![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/2412:39 pm -
2 stops13h 30m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 9/7![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 11/712:39 pm -
2 stops11h 20m
Sat 11/143:20 pm -
1 stop20h 50m
Deal found 9/6![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Mon 9/2811:21 am -
1 stop22h 14m
Wed 9/308:45 am -
1 stop24h 53m
Deal found 9/6![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/110:28 am -
1 stop27h 14m
Thu 10/85:11 pm -
2 stops42h 28m
Deal found 9/3![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/810:18 am -
1 stop27h 13m
Mon 10/197:20 am -
1 stop10h 51m
Deal found 9/5![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2312:39 pm -
2 stops21h 34m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Mon 10/57:13 pm -
1 stop14h 22m
Wed 10/74:39 pm -
2 stops16h 49m
Deal found 9/5![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 9/2612:39 pm -
2 stops21h 34m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 10/712:39 pm -
2 stops20h 39m
Sun 10/186:42 pm -
1 stop23h 29m
Deal found 9/4![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2510:48 am -
2 stops23h 26m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2312:39 pm -
2 stops21h 34m
Sat 9/2611:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/7![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2410:56 am -
1 stop23h 17m
Thu 10/111:08 am -
2 stops24h 28m
Deal found 9/3![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:56 am -
1 stop23h 17m
Sun 10/411:08 am -
2 stops24h 28m
Deal found 9/4![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 10/312:39 pm -
2 stops21h 34m
Sat 10/1011:17 am -
1 stop22h 59m
Deal found 9/3![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:39 pm -
2 stops21h 34m
Wed 9/2311:12 am -
1 stop23h 04m
Deal found 9/4![Multiple Airlines logo]()
$437
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:56 am -
1 stop23h 01m
Mon 11/212:37 pm -
2 stops48h 02m
Deal found 9/4![Multiple Airlines logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 9/1912:39 pm -
2 stops21h 34m
Sat 9/2611:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2410:56 am -
1 stop23h 17m
Sun 9/2711:08 am -
2 stops24h 28m
Deal found 9/3![Multiple Airlines logo]()
$469
Last-minute flights from Stewart to Puerto RicoDiscover last-minute flight deals from Stewart to Puerto Rico. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Puerto Rico. Data last updated September 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2312:39 pm -
2 stops21h 34m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2312:39 pm -
2 stops21h 34m
Sat 9/2611:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 9/2510:48 am -
2 stops23h 26m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Sat 9/2612:39 pm -
2 stops21h 34m
Wed 9/3011:12 am -
1 stop23h 04m
Deal found 9/3![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:48 am -
1 stop25h 54m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/4![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops21h 18m
Wed 10/1411:17 am -
1 stop22h 59m
Deal found 9/7![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/1111:53 am -
1 stop25h 38m
Wed 10/148:45 am -
1 stop24h 43m
Deal found 9/5![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/1811:53 am -
1 stop25h 38m
Wed 10/218:45 am -
1 stop25h 03m
Deal found 9/5![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1811:53 am -
1 stop25h 38m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 9/3![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1811:53 am -
1 stop25h 38m
Sat 10/243:20 pm -
1 stop19h 48m
Deal found 9/7![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/2511:58 am -
1 stop25h 33m
Wed 10/288:45 am -
1 stop25h 03m
Deal found 9/6![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/2910:38 am -
1 stop26h 08m
Wed 11/48:45 am -
1 stop26h 25m
Deal found 9/6![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 September 8, 2026.
Search for one-way flight options from Stewart to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/2511:58 am -
1 stop25h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$117
This Trip.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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.
Sun 10/1811:53 am -
1 stop25h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/1512:00 pm -
1 stop24h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:48 am -
1 stop25h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:38 am -
1 stop26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:18 am -
1 stop27h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/197:01 pm -
1 stop14h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From 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 10/1012:39 pm -
2 stops21h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/312:39 pm -
2 stops21h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Fri 10/28:48 pm -
1 stop13h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/1112:39 pm -
2 stops21h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/712:39 pm -
2 stops21h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$203
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 September 8, 2026.
Round-trip from | $234 (Kiwi.com) |
|---|---|
One-way from | $117 (Kiwi.com) |
Popular in | July |
Cheapest in | October |
Average price | $285 |
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 September 8, 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
Sun 10/18
11:53 am-1:31 pm
1 stop25h 38m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sun 11/15
12:00 pm-1:25 pm
1 stop24h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 10/29
10:38 am-12:46 pm
1 stop26h 08m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 10/15
10:18 am-1:31 pm
1 stop27h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 11/5
11:00 am-1:25 pm
1 stop25h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$140
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Mon 10/26
7:01 pm-9:15 am
1 stop14h 14m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 9/26
12:39 pm-9:35 am
2 stops20h 56m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 10/22
10:38 am-1:31 pm
1 stop26h 53m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$172
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 10/3
12:39 pm-11:58 pm
2 stops35h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$183
New WindsorAguadilla
SWF New Windsor Stewart - BQN Aguadilla Borinquen
SWFBQN
New Windsor Stewart
Sat 10/10
12:39 pm-9:57 am
2 stops21h 18m
Aguadilla Borinquen
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
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 September 8, 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
7.1
Food
6.6
Crew
7.9
Entertainment
7.2
Comfort
7.4
Boarding
7.3
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
Overall
7.1
Food
6.6
Crew
7.9
Entertainment
7.2
Comfort
7.4
Boarding
7.3
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 September 8, 2026.
Popular flight searches
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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 September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% |