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Stewart

$127+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap 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 January 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/17. 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 5/67:05 pm
SJU
-
SWF
1 stop13h 53m
Multiple Airlines
Sun 5/109:38 am
SWF
-
SJU
1 stop12h 31m
Multiple Airlines
Deal found 1/17$505
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 4/82:43 am
BQN
-
SWF
1 stop8h 25m
Multiple Airlines
Sun 4/1211:48 am
SWF
-
BQN
1 stop7h 54m
Multiple Airlines
Deal found 1/20$524
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 3/43:53 am
SJU
-
SWF
1 stop8h 15m
Multiple Airlines
Fri 3/612:11 pm
SWF
-
SJU
2 stops13h 47m
Multiple Airlines
Deal found 1/19$530
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/58:05 pm
SJU
-
SWF
2 stops16h 26m
Multiple Airlines
Sun 2/811:48 am
SWF
-
SJU
1 stop10h 45m
Multiple Airlines
Deal found 1/20$547
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 1/298:05 pm
SJU
-
SWF
2 stops16h 26m
Multiple Airlines
Sun 2/112:13 pm
SWF
-
SJU
1 stop11h 55m
Multiple Airlines
Deal found 1/18$548
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 5/77:05 pm
SJU
-
SWF
2 stops16h 30m
Multiple Airlines
Sun 5/109:38 am
SWF
-
SJU
1 stop12h 31m
Multiple Airlines
Deal found 1/17$553
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 3/183:08 am
SJU
-
SWF
1 stop8h 00m
Multiple Airlines
Sun 3/2211:48 am
SWF
-
SJU
1 stop10h 57m
Multiple Airlines
Deal found 1/19$558
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 2/113:53 am
SJU
-
SWF
1 stop8h 15m
Multiple Airlines
Thu 2/1911:48 am
SWF
-
SJU
1 stop10h 21m
Multiple Airlines
Deal found 1/18$585
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/253:53 am
SJU
-
SWF
1 stop8h 15m
Multiple Airlines
Sun 3/111:48 am
SWF
-
SJU
1 stop12h 06m
Multiple Airlines
Deal found 1/20$606
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/113:58 am
BQN
-
SWF
1 stop8h 10m
Multiple Airlines
Mon 2/1612:11 pm
SWF
-
BQN
2 stops13h 51m
Multiple Airlines
Deal found 1/19$689

Find 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 January 20, 2026.

Round-trip from

$505
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$200
From Puerto Rico to New Windsor Stewart
Search Deals
One-way flight from Puerto Rico to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 20, 2026.
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

AguadillaNew Windsor

BQN - SWF

BQNSWF

Aguadilla Borinquen

Wed 4/8

2:43 am-11:08 am

1 stop8h 25m

New Windsor Stewart

Sun 4/12

11:48 am-7:42 pm

1 stop7h 54m

$524

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/4

3:53 am-11:08 am

1 stop8h 15m

New Windsor Stewart

Fri 3/6

12:11 pm-2:58 am

2 stops13h 47m

$530

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 2/5

8:05 pm-11:31 am

2 stops16h 26m

New Windsor Stewart

Sun 2/8

11:48 am-11:33 pm

1 stop10h 45m

$547

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 1/29

8:05 pm-11:31 am

2 stops16h 26m

New Windsor Stewart

Sun 2/1

12:13 pm-1:08 am

1 stop11h 55m

$548

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/18

3:08 am-11:08 am

1 stop8h 00m

New Windsor Stewart

Sun 3/22

11:48 am-10:45 pm

1 stop10h 57m

$558

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 2/11

3:53 am-11:08 am

1 stop8h 15m

New Windsor Stewart

Thu 2/19

11:48 am-11:09 pm

1 stop10h 21m

$585

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 2/25

3:53 am-11:08 am

1 stop8h 15m

New Windsor Stewart

Sun 3/1

11:48 am-12:54 am

1 stop12h 06m

$606

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 3/19

1:45 am-11:31 am

2 stops9h 46m

New Windsor Stewart

Sun 3/22

11:48 am-10:03 pm

1 stop10h 15m

$608

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 3/5

8:05 pm-11:31 am

2 stops16h 26m

New Windsor Stewart

Sun 3/8

11:48 am-10:09 pm

1 stop10h 21m

$613

AguadillaNew Windsor

BQN - SWF

BQNSWF

Aguadilla Borinquen

Wed 2/11

3:58 am-11:08 am

1 stop8h 10m

New Windsor Stewart

Mon 2/16

12:11 pm-3:02 am

2 stops13h 51m

$689

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 27 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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