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San Juan

$128+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
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 December 8, 2025.

This Mytrip deal was found by Cheapflights users on 12/6. 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.
Mon 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Thu 12/184:10 amSJU - SWF
1 stop14h 56mMultiple Airlines
Deal found 12/6$295
This Mytrip deal was found by Cheapflights users on 12/5. 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.
Fri 12/1212:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 12/5$312
This Mytrip deal was found by Cheapflights users on 12/6. 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.
Mon 12/812:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 12/6$328
This Mytrip deal was found by Cheapflights users on 12/7. 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.
Fri 12/1212:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/146:00 amSJU - SWF
2 stops30h 37mMultiple Airlines
Deal found 12/7$372
This Mytrip deal was found by Cheapflights users on 12/6. 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.
Mon 12/812:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/1411:38 amSJU - SWF
2 stops24h 59mMultiple Airlines
Deal found 12/6$386

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 December 8, 2025.

Round-trip from

$298
(Mytrip)

One-way from

$128
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$365
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. 8% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 8, 2025.
Use the filters below to find and compare flights from New Windsor to San Juan that are best for you.

Fly from

Stewart

Fly to

San Juan

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 1/5

11:37 am-10:05 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Sat 1/10

2:59 am-10:19 am

2 stops32h 20m

$298

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 12/12

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:00 am-11:37 am

2 stops30h 37m

$372

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 1/1

11:43 am-2:50 am

1 stop14h 07m

San Juan Luis Munoz Marin Intl

Thu 1/8

9:04 am-10:19 am

1 stop26h 15m

$374

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 12/11

11:43 am-12:16 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Sun 12/14

4:10 am-11:37 am

1 stop8h 27m

$412

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 12/12

12:27 pm-11:25 pm

3 stops33h 58m

San Juan Luis Munoz Marin Intl

Sun 12/14

4:10 am-11:37 am

1 stop8h 27m

$415

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 12/18

11:43 am-2:12 am

1 stop13h 29m

San Juan Luis Munoz Marin Intl

Thu 12/25

4:10 am-11:07 am

1 stop7h 57m

$472

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 1/9

12:11 pm-2:50 am

2 stops13h 39m

San Juan Luis Munoz Marin Intl

Sat 1/10

3:55 am-11:33 am

1 stop8h 38m

$563

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 12/19

6:56 pm-11:58 am

1 stop16h 02m

San Juan Luis Munoz Marin Intl

Thu 12/25

4:10 am-11:07 am

1 stop7h 57m

$567

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 1/9

11:09 am-11:44 pm

1 stop11h 35m

$128

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/15

12:27 pm-12:45 am

1 stop11h 18m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 17 results
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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

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

Currently, March is the cheapest month in which you can book a flight from New Windsor to San Juan (average of $62). Flying from New Windsor to San Juan in August is currently the most expensive (average of $138). 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 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.

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

    Currently, March is the cheapest month in which you can book a flight from New Windsor to San Juan (average of $62). Flying from New Windsor to San Juan in August is currently the most expensive (average of $138). 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

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Alternative routes for Stewart to San Juan

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