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Stewart

$114+ Cheap flights from Puerto Rico to New Windsor (SWF)

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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Dec 31 — Jan 71
Wed 12/31
Wed 1/7
1 adult, Economy
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Cheap flight deals from Puerto Rico to Stewart

Keep the following information in mind while searching for Puerto Rico to Stewart flight deals. Data was last updated December 1, 2025.

Round-trip from

$244
(Mytrip)

One-way from

$114
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$251
From Puerto Rico to New Windsor Stewart
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One-way flight from Puerto Rico to New Windsor Stewart
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Highest demand for flights based on searches. 11% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Find flight deals from Puerto Rico to Stewart

Cheapest flights from Puerto Rico to Stewart
Explore the most affordable flight options available from Puerto Rico to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 1, 2025.

This Mytrip deal was found by Cheapflights users on 11/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/114:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Mon 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Deal found 11/29$244
This Mytrip deal was found by Cheapflights users on 11/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Mon 12/812:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Deal found 11/29$257
This Mytrip deal was found by Cheapflights users on 11/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/74:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Fri 12/1212:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Deal found 11/30$322
This Mytrip deal was found by Cheapflights users on 11/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:38 amSJU - SWF
2 stops24h 59mMultiple Airlines
Mon 12/812:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Deal found 11/30$367
This eDestinos deal was found by Cheapflights users on 11/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amSJU - SWF
1 stop13h 06mMultiple Airlines
Mon 12/228:25 pmSWF - SJU
1 stop15h 04mMultiple Airlines
Deal found 11/29$375
This eDestinos deal was found by Cheapflights users on 11/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:35 amSJU - SWF
1 stop28h 12mMultiple Airlines
Fri 1/211:57 amSWF - SJU
1 stop25h 02mMultiple Airlines
Deal found 11/29$401
This Mytrip deal was found by Cheapflights users on 11/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/284:10 amSJU - SWF
1 stop7h 37mMultiple Airlines
Mon 1/511:37 amSWF - SJU
1 stop9h 28mMultiple Airlines
Deal found 11/29$402
This Mytrip deal was found by Cheapflights users on 11/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amSJU - SWF
2 stops30h 37mMultiple Airlines
Fri 12/196:56 pmSWF - SJU
1 stop16h 02mMultiple Airlines
Deal found 11/30$432
This Kiwi.com deal was found by Cheapflights users on 11/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:55 amBQN - SWF
2 stops8h 49mMultiple Airlines
Thu 1/111:43 amSWF - BQN
1 stop14h 27mMultiple Airlines
Deal found 11/29$721
This Kiwi.com deal was found by Cheapflights users on 11/29. 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 12/273:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Mon 1/512:24 pmSWF - BQN
2 stops13h 34mMultiple Airlines
Deal found 11/29$728
This Kiwi.com deal was found by Cheapflights users on 11/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:55 amBQN - SWF
2 stops8h 49mMultiple Airlines
Sun 12/711:43 amSWF - BQN
1 stop14h 15mMultiple Airlines
Deal found 11/29$738
This Kiwi.com deal was found by Cheapflights users on 11/29. 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.
Mon 12/293:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Mon 1/512:24 pmSWF - BQN
2 stops13h 34mMultiple Airlines
Deal found 11/29$751

Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Stewart 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 December 1, 2025.
Use the filters below to find and compare flights from Puerto Rico to New Windsor that are best for you.

Fly from

Puerto Rico

Fly to

Stewart

Route

Depart

Return

Price

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 12/11

4:10 am-11:37 am

1 stop8h 27m

New Windsor Stewart

Mon 12/15

12:27 pm-12:45 am

1 stop11h 18m

$244

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 12/4

4:10 am-11:37 am

1 stop8h 27m

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

$257

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 1/29

10:52 am-10:19 am

2 stops24h 27m

New Windsor Stewart

Mon 2/2

11:09 am-9:47 am

2 stops21h 38m

$263

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 12/4

11:38 am-11:37 am

2 stops24h 59m

New Windsor Stewart

Mon 12/8

12:27 pm-12:45 am

1 stop11h 18m

$367

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Fri 12/19

6:00 am-6:06 pm

1 stop13h 06m

New Windsor Stewart

Mon 12/22

8:25 pm-12:29 pm

1 stop15h 04m

$375

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sun 12/28

7:35 am-10:47 am

1 stop28h 12m

New Windsor Stewart

Fri 1/2

11:57 am-1:59 pm

1 stop25h 02m

$401

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sun 12/28

4:10 am-10:47 am

1 stop7h 37m

New Windsor Stewart

Mon 1/5

11:37 am-10:05 pm

1 stop9h 28m

$401

AguadillaNew Windsor

BQN - SWF

BQNSWF

Aguadilla Borinquen

Thu 12/25

3:55 am-11:44 am

2 stops8h 49m

New Windsor Stewart

Thu 1/1

11:43 am-3:10 am

1 stop14h 27m

$721

AguadillaNew Windsor

BQN - SWF

BQNSWF

Aguadilla Borinquen

Sat 12/27

3:55 am-11:03 am

1 stop8h 08m

New Windsor Stewart

Mon 1/5

12:24 pm-2:58 am

2 stops13h 34m

$728

AguadillaNew Windsor

BQN - SWF

BQNSWF

Aguadilla Borinquen

Mon 12/29

3:55 am-11:03 am

1 stop8h 08m

New Windsor Stewart

Mon 1/5

12:24 pm-2:58 am

2 stops13h 34m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/29

Showing 1-10 of 32 results
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Best time to book a flight from Puerto Rico to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Puerto Rico with our price prediction graph.
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 Puerto Rico to New Windsor

What is the cheapest month to book a flight from Puerto Rico to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Puerto Rico to New Windsor (average of $51). Flying from Puerto Rico to New Windsor in August is currently the most expensive (average of $118). 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.

Related info for your journey

Find useful and relevant information for your journey from Puerto Rico to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Puerto Rico?

    Most people fly into New Windsor Stewart (SWF) if they book a flight to New Windsor from Puerto Rico. Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

  • Can I find deals for flights from Puerto Rico to Stewart that include hotel bookings?

    Yes. In addition to deals on Puerto Rico to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Puerto Rico to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Puerto Rico to Stewart.

  • Can I find deals for business class flights from Puerto Rico to Stewart?

    Yes. Cheapflights offers flight deals from Puerto Rico to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Puerto Rico to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Puerto Rico to New Windsor (average of $51). Flying from Puerto Rico to New Windsor in August is currently the most expensive (average of $118). 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.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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Alternative routes for Puerto Rico to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
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