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San Juan

$103+ Cheap flights from New Windsor (SWF) to San Juan

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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheap flight deals from Stewart to San Juan

Cheapest flights from Stewart to San Juan
Explore the most affordable flight options available from Stewart to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/28. 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
SWF
-
SJU
1 stop13h 20m
Multiple Airlines
Wed 10/215:12 pm
SJU
-
SWF
1 stop16h 36m
Multiple Airlines
Deal found 7/28$186
This Kiwi.com deal was found by Cheapflights users on 7/28. 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
SWF
-
SJU
1 stop25h 46m
Multiple Airlines
Wed 10/78:45 am
SJU
-
SWF
1 stop24h 43m
Multiple Airlines
Deal found 7/28$195
This Kiwi.com deal was found by Cheapflights users on 7/28. 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
SWF
-
SJU
1 stop13h 20m
Multiple Airlines
Sat 10/175:12 pm
SJU
-
SWF
1 stop17h 51m
Multiple Airlines
Deal found 7/28$198
This Kiwi.com deal was found by Cheapflights users on 7/27. 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
SWF
-
SJU
1 stop25h 46m
Multiple Airlines
Wed 10/215:12 pm
SJU
-
SWF
1 stop16h 36m
Multiple Airlines
Deal found 7/27$202
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 10/1811:53 am
SWF
-
SJU
1 stop11h 45m
Multiple Airlines
Wed 10/285:12 pm
SJU
-
SWF
1 stop16h 36m
Multiple Airlines
Deal found 7/29$203
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 10/2210:38 am
SWF
-
SJU
1 stop13h 00m
Multiple Airlines
Wed 10/285:12 pm
SJU
-
SWF
1 stop16h 36m
Multiple Airlines
Deal found 7/29$204
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/2910:38 am
SWF
-
SJU
1 stop13h 00m
Multiple Airlines
Wed 11/46:12 pm
SJU
-
SWF
1 stop16h 58m
Multiple Airlines
Deal found 7/30$209
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/1811:53 am
SWF
-
SJU
1 stop11h 45m
Multiple Airlines
Wed 10/215:12 pm
SJU
-
SWF
1 stop16h 36m
Multiple Airlines
Deal found 8/1$219

Find flight deals from Stewart to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to San Juan (PR1). 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 1, 2026.

Round-trip from

$186
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$348
From New Windsor Stewart to San Juan
Search Deals
One-way flight from New Windsor Stewart to San Juan
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to San Juan 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 1, 2026.
Use the filters below to find and compare flights from New Windsor to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/15

10:18 am-11:38 pm

1 stop13h 20m

San Juan Luis Munoz Marin Intl

Wed 10/21

5:12 pm-9:48 am

1 stop16h 36m

$192

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/1

10:28 am-1:34 pm

1 stop27h 06m

San Juan Luis Munoz Marin Intl

Wed 10/7

8:45 am-9:28 am

1 stop24h 43m

$230

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/29

10:38 am-11:38 pm

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Sat 11/7

6:12 pm-11:10 am

1 stop17h 58m

$239

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 9/6

7:30 pm-4:11 pm

1 stop20h 41m

San Juan Luis Munoz Marin Intl

Wed 9/16

6:42 pm-10:16 am

1 stop15h 34m

$304

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 10/2

8:48 pm-2:18 pm

1 stop17h 30m

San Juan Luis Munoz Marin Intl

Tue 10/6

6:05 pm-11:39 am

2 stops17h 34m

$312

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 9/27

11:13 am-11:58 pm

1 stop12h 45m

San Juan Luis Munoz Marin Intl

Sun 10/4

6:42 pm-6:23 pm

1 stop23h 41m

$328

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 9/3

7:30 pm-12:56 am

2 stops29h 26m

San Juan Luis Munoz Marin Intl

Wed 9/9

6:42 pm-10:16 am

1 stop15h 34m

$335

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 8/29

12:05 pm-12:56 am

2 stops12h 51m

San Juan Luis Munoz Marin Intl

Mon 8/31

3:10 am-11:08 am

1 stop7h 58m

$357

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 8/12

7:58 pm-7:57 am

1 stop11h 59m

San Juan Luis Munoz Marin Intl

Wed 8/19

6:35 am-12:10 pm

1 stop29h 35m

$378

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 8/5

12:05 pm-9:43 pm

2 stops33h 38m

San Juan Luis Munoz Marin Intl

Mon 8/10

10:48 pm-11:08 am

1 stop12h 20m

$462

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from Stewart to San Juan

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

No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Stewart to San Juan. 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 from for flights from New Windsor to San Juan?

    If you book a flight to San Juan from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor. There are 0 flights from Stewart to San Juan per day from 0 different airlines.

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

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

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

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

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

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

See more FAQs

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