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San Juan

$150+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
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 May 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/2. 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 7/2912:05 pm
SWF
-
SJU
2 stops12h 36m
Multiple Airlines
Wed 8/56:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 5/2$324
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Wed 8/512:05 pm
SWF
-
SJU
2 stops11h 24m
Multiple Airlines
Wed 8/126:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 4/30$344
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 7/812:05 pm
SWF
-
SJU
2 stops12h 36m
Multiple Airlines
Wed 8/56:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 5/4$348
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 8/211:45 am
SWF
-
SJU
1 stop12h 56m
Multiple Airlines
Wed 8/56:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 5/2$359
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 9/212:05 pm
SWF
-
SJU
2 stops12h 18m
Multiple Airlines
Sat 9/59:24 am
SJU
-
SWF
1 stop23h 34m
Multiple Airlines
Deal found 5/4$372
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sat 8/1512:05 pm
SWF
-
SJU
1 stop28h 37m
Multiple Airlines
Sat 8/227:00 am
SJU
-
SWF
2 stops29h 10m
Multiple Airlines
Deal found 4/30$378
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 8/812:05 pm
SWF
-
SJU
2 stops12h 36m
Multiple Airlines
Fri 8/143:06 am
SJU
-
SWF
1 stop12h 44m
Multiple Airlines
Deal found 5/2$382
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/2510:28 am
SWF
-
SJU
1 stop26h 38m
Multiple Airlines
Wed 7/15:15 pm
SJU
-
SWF
2 stops16h 23m
Multiple Airlines
Deal found 4/30$384
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 8/1311:45 am
SWF
-
SJU
1 stop12h 56m
Multiple Airlines
Mon 8/176:45 pm
SJU
-
SWF
2 stops40h 40m
Multiple Airlines
Deal found 5/4$389
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Tue 9/111:48 am
SWF
-
SJU
2 stops12h 56m
Multiple Airlines
Sat 9/59:24 am
SJU
-
SWF
1 stop23h 34m
Multiple Airlines
Deal found 5/3$397
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Tue 9/111:48 am
SWF
-
SJU
1 stop14h 06m
Multiple Airlines
Tue 9/88:00 am
SJU
-
SWF
1 stop27h 39m
Multiple Airlines
Deal found 5/3$399

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 May 5, 2026.

Round-trip from

$324
(Kiwi.com)

One-way from

$150
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$302
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. 1% potential increase in price ($4 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 May 2026
Search Deals

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 May 5, 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

Wed 9/2

12:05 pm-12:23 am

2 stops12h 18m

San Juan Luis Munoz Marin Intl

Sat 9/5

9:24 am-8:58 am

1 stop23h 34m

$372

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 8/15

12:05 pm-4:42 pm

1 stop28h 37m

San Juan Luis Munoz Marin Intl

Sat 8/22

7:00 am-12:10 pm

2 stops29h 10m

$378

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 8/9

10:28 am-4:05 pm

1 stop29h 37m

San Juan Luis Munoz Marin Intl

Tue 8/18

5:15 pm-11:25 am

2 stops18h 10m

$421

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 8/8

12:05 pm-4:42 pm

1 stop28h 37m

San Juan Luis Munoz Marin Intl

Wed 8/12

6:31 pm-8:58 am

1 stop14h 27m

$427

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 8/26

12:05 pm-4:34 pm

1 stop28h 29m

San Juan Luis Munoz Marin Intl

Mon 8/31

3:06 am-11:08 am

1 stop8h 02m

$447

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Tue 9/1

11:48 am-1:54 am

1 stop14h 06m

San Juan Luis Munoz Marin Intl

Sun 9/6

6:00 am-6:40 pm

1 stop12h 40m

$457

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 7/22

12:05 pm-12:28 am

2 stops12h 23m

San Juan Luis Munoz Marin Intl

Sat 7/25

5:22 pm-10:55 am

1 stop17h 33m

$475

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 6/3

12:05 pm-4:01 am

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Sat 6/6

8:13 pm-8:58 am

1 stop12h 45m

$476

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Tue 7/28

11:48 am-2:11 am

1 stop14h 23m

San Juan Luis Munoz Marin Intl

Tue 8/4

6:45 pm-9:38 am

2 stops38h 53m

$485

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 7/4

12:05 pm-12:37 am

2 stops12h 32m

San Juan Luis Munoz Marin Intl

Wed 7/8

6:31 pm-8:58 am

1 stop14h 27m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

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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