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Stewart

$162+ Cheap flights from San Juan 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from San Juan to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 17, 2025.

Round-trip from

$443
(Mytrip)

One-way from

$162
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$270
From San Juan to New Windsor Stewart
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One-way flight from San Juan to New Windsor Stewart
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Highest demand for flights based on searches. 10% potential increase in price ($24 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 August 2025
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Find flight deals from San Juan to Stewart

Cheapest flights from San Juan to Stewart
Explore the most affordable flight options available from San Juan to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This Mytrip deal was found by Cheapflights users on 8/15. 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 8/288:00 amSJU - SWF
2 stops29h 05mMultiple Airlines
Mon 9/11:55 pmSWF - SJU
1 stop7h 53mMultiple Airlines
Deal found 8/15$443
This Mytrip deal was found by Cheapflights users on 8/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/212:11 amSJU - SWF
2 stops14h 35mMultiple Airlines
Fri 8/291:55 pmSWF - SJU
1 stop7h 53mMultiple Airlines
Deal found 8/17$509
This Mytrip deal was found by Cheapflights users on 8/15. 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 8/282:11 amSJU - SWF
2 stops10h 54mMultiple Airlines
Mon 9/11:55 pmSWF - SJU
1 stop7h 53mMultiple Airlines
Deal found 8/15$546
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/13:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Mon 10/612:24 pmSWF - SJU
2 stops13h 20mMultiple Airlines
Deal found 8/15$597
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/243:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Sun 9/2811:43 amSWF - SJU
1 stop13h 11mMultiple Airlines
Deal found 8/16$606
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/33:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Mon 9/812:24 pmSWF - SJU
2 stops12h 30mMultiple Airlines
Deal found 8/15$607
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/173:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Sun 9/2111:43 amSWF - SJU
1 stop12h 16mMultiple Airlines
Deal found 8/15$650

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan 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 August 17, 2025.
Use the filters below to find and compare flights from San Juan to New Windsor that are best for you.

Fly from

San Juan

Fly to

Stewart

Route

Depart

Return

Price

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 8/28

8:00 am-1:05 pm

2 stops29h 05m

New Windsor Stewart

Mon 9/1

1:55 pm-9:48 pm

1 stop7h 53m

$443

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 8/21

2:11 am-4:46 pm

2 stops14h 35m

New Windsor Stewart

Fri 8/29

1:55 pm-9:48 pm

1 stop7h 53m

$509

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 8/28

2:11 am-1:05 pm

2 stops10h 54m

New Windsor Stewart

Mon 9/1

1:55 pm-9:48 pm

1 stop7h 53m

$546

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 10/1

3:39 am-11:03 am

1 stop7h 24m

New Windsor Stewart

Mon 10/6

12:24 pm-1:44 am

2 stops13h 20m

$597

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 9/24

3:39 am-11:03 am

1 stop7h 24m

New Windsor Stewart

Sun 9/28

11:43 am-12:54 am

1 stop13h 11m

$606

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 9/3

3:39 am-11:03 am

1 stop7h 24m

New Windsor Stewart

Mon 9/8

12:24 pm-12:54 am

2 stops12h 30m

$607

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 8/28

10:04 am-7:12 pm

1 stop9h 08m

New Windsor Stewart

Tue 9/2

12:36 pm-11:57 pm

1 stop11h 21m

$648

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 10/16

11:51 am-10:41 am

1 stop22h 50m

$162

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 10/23

11:51 am-10:41 am

1 stop22h 50m

$162

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sat 10/4

12:28 am-10:11 am

2 stops33h 43m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 13 results
1
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Best time to book a flight from San Juan to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from San Juan 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 San Juan to New Windsor

What is the cheapest month to book a flight from San Juan to New Windsor?

Currently, October is the cheapest month in which you can book a flight from San Juan to New Windsor (average of $109). Flying from San Juan to New Windsor in December is currently the most expensive (average of $202). 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 San Juan 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 San Juan?

    New Windsor Stewart (SWF) is the airport you will fly into if you book a flight from San Juan to New Windsor. You should not have trouble finding flights to Stewart from San Juan; the airport handles an average of 0 inbound flights from San Juan per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the New Windsor airport from San Juan. It is only a 4.3 mi journey from Stewart (SWF) to New Windsor’s city center.

  • Can I find deals for flights from San Juan to Stewart that include hotel bookings?

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

  • How can I find direct flights from San Juan to Stewart?

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

  • Can I find deals for business class flights from San Juan to Stewart?

    Yes. Cheapflights offers flight deals from San Juan 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 San Juan to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from San Juan to New Windsor (average of $109). Flying from San Juan to New Windsor in December is currently the most expensive (average of $202). 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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