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San Juan

$122+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
1 adult, Economy
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Cheap 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 noviembre 6, 2025.

Round-trip from

$330
(Mytrip)

One-way from

$122
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$266
From New Windsor Stewart to San Juan
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One-way flight from New Windsor Stewart to San Juan
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Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 noviembre 6, 2025.

This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
dom. 12/74:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/4$326
This Mytrip deal was found by Cheapflights users on 11/5. 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.
vie. 12/1212:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
dom. 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/5$330
This Mytrip deal was found by Cheapflights users on 11/5. 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.
vie. 12/512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
jue. 12/114:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/5$335
This Mytrip deal was found by Cheapflights users on 11/5. 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.
lun. 12/812:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
jue. 12/114:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/5$338
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
jue. 11/2011:06 amSWF - SJU
1 stop11h 03mMultiple Airlines
mar. 11/255:19 pmSJU - SWF
1 stop19h 08mMultiple Airlines
Deal found 11/4$376
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2011:43 amSWF - SJU
1 stop11h 41mMultiple Airlines
dom. 11/233:59 amSJU - SWF
1 stop29h 54mMultiple Airlines
Deal found 11/5$399
This Mytrip deal was found by Cheapflights users on 11/6. 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.
lun. 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
dom. 12/284:10 amSJU - SWF
1 stop7h 37mMultiple Airlines
Deal found 11/6$415
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/2111:12 amSWF - SJU
1 stop8h 15mMultiple Airlines
mar. 11/256:00 amSJU - SWF
2 stops30h 27mMultiple Airlines
Deal found 11/4$421

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 noviembre 6, 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

vie. 12/5

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

dom. 12/7

4:10 am-11:37 am

1 stop8h 27m

$326

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

vie. 12/12

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

dom. 12/14

4:10 am-11:37 am

1 stop8h 27m

$334

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 12/8

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

jue. 12/11

4:10 am-11:37 am

1 stop8h 27m

$338

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 2/22

7:28 pm-11:37 pm

1 stop27h 09m

San Juan Luis Munoz Marin Intl

jue. 2/26

9:37 pm-10:13 am

1 stop13h 36m

$349

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

jue. 11/20

11:43 am-12:24 am

1 stop11h 41m

San Juan Luis Munoz Marin Intl

lun. 11/24

11:55 am-8:53 am

2 stops21h 58m

$423

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

vie. 11/21

11:12 am-12:24 am

2 stops12h 12m

San Juan Luis Munoz Marin Intl

mar. 11/25

11:54 am-11:27 am

2 stops24h 33m

$432

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

vie. 3/6

11:02 am-2:50 am

1 stop14h 48m

San Juan Luis Munoz Marin Intl

sáb. 3/7

3:55 am-11:08 am

1 stop7h 13m

$443

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

lun. 12/22

8:25 pm-12:29 pm

1 stop15h 04m

San Juan Luis Munoz Marin Intl

jue. 1/8

5:20 pm-10:19 am

1 stop17h 59m

$464

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

vie. 1/9

11:09 am-12:27 pm

2 stops24h 18m

San Juan Luis Munoz Marin Intl

sáb. 1/17

2:59 am-10:19 am

2 stops32h 20m

$477

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 11/16

11:43 am-11:19 am

1 stop22h 36m

San Juan Luis Munoz Marin Intl

mié. 11/19

1:26 pm-11:03 am

2 stops22h 37m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 19 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

See prices for flight routes from nearby airports that may be better suited for you.
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