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$128+ Cheap flights from New Windsor (SWF) to Puerto Rico

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Dec 31 — Jan 71
Wed 12/31
Wed 1/7
1 adult, Economy
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Cheap flight deals from Stewart to Puerto Rico

Keep the following information in mind while searching for Stewart to Puerto Rico flight deals. Data was last updated December 1, 2025.

Round-trip from

$232
(Mytrip)

One-way from

$128
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$365
From New Windsor Stewart to Puerto Rico
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One-way flight from New Windsor Stewart to Puerto Rico
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Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Find flight deals from Stewart to Puerto Rico

Cheapest flights from Stewart to Puerto Rico
Explore the most affordable flight options available from Stewart to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 1, 2025.

This Mytrip deal was found by Cheapflights users on 11/28. 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 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
Thu 12/184:10 amSJU - SWF
1 stop14h 56mMultiple Airlines
Deal found 11/28$232
This Mytrip deal was found by Cheapflights users on 12/1. 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 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
Thu 12/114:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 12/1$240
This Mytrip deal was found by Cheapflights users on 12/1. 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 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 12/1$258
This Mytrip deal was found by Cheapflights users on 11/29. 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 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 11/29$267
This Mytrip deal was found by Cheapflights users on 11/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/74:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 11/30$271
This Mytrip deal was found by Cheapflights users on 11/30. 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 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
Thu 12/115:00 pmSJU - SWF
2 stops19h 37mMultiple Airlines
Deal found 11/30$274
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Tue 12/2311:43 amSWF - BQN
1 stop14h 27mMultiple Airlines
Sat 1/103:43 amBQN - SWF
1 stop8h 50mMultiple Airlines
Deal found 12/1$526
This Kiwi.com deal was found by Cheapflights users on 11/30. 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.
Tue 12/2311:43 amSWF - BQN
1 stop29h 04mMultiple Airlines
Thu 12/253:55 amBQN - SWF
2 stops8h 49mMultiple Airlines
Deal found 11/30$561
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 12/1111:43 amSWF - BQN
1 stop14h 15mMultiple Airlines
Sun 12/143:55 amBQN - SWF
2 stops8h 49mMultiple Airlines
Deal found 11/30$639
This Kiwi.com deal was found by Cheapflights users on 11/30. 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.
Tue 12/2311:43 amSWF - BQN
1 stop14h 27mMultiple Airlines
Mon 12/296:42 pmBQN - SWF
1 stop17h 21mMultiple Airlines
Deal found 11/30$641
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Mon 12/2212:24 pmSWF - BQN
2 stops13h 46mMultiple Airlines
Mon 12/296:42 pmBQN - SWF
1 stop17h 21mMultiple Airlines
Deal found 12/1$647
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Thu 12/1811:43 amSWF - BQN
1 stop14h 27mMultiple Airlines
Mon 12/223:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Deal found 12/1$663

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Puerto Rico 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 1, 2025.
Use the filters below to find and compare flights from New Windsor to Puerto Rico that are best for you.

Fly from

Stewart

Fly to

Puerto Rico

Route

Depart

Return

Price

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

Thu 12/18

4:10 am-6:06 pm

1 stop14h 56m

$232

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

4:10 am-11:37 am

1 stop8h 27m

$298

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 1/19

12:11 pm-11:29 pm

2 stops10h 18m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:05 pm-6:43 pm

1 stop23h 38m

$329

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

5:00 pm-11:37 am

2 stops19h 37m

$330

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/15

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Fri 12/19

10:17 pm-8:55 am

1 stop11h 38m

$332

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 2/22

11:52 am-12:27 pm

2 stops23h 35m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:59 am-11:02 am

2 stops33h 03m

$354

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 2/26

11:52 am-7:55 pm

2 stops31h 03m

San Juan Luis Munoz Marin Intl

Wed 3/4

3:55 am-11:08 am

1 stop8h 13m

$359

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 2/26

11:52 am-7:55 pm

2 stops31h 03m

San Juan Luis Munoz Marin Intl

Sun 3/8

8:37 pm-10:12 am

1 stop13h 35m

$376

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 2/19

12:22 pm-12:27 pm

2 stops23h 05m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:59 am-11:02 am

2 stops33h 03m

$382

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 3/1

11:48 am-2:50 am

1 stop14h 02m

San Juan Luis Munoz Marin Intl

Wed 3/4

3:55 am-11:08 am

1 stop8h 13m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/29

Showing 1-10 of 37 results
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Best time to book a flight from Stewart to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico 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 Puerto Rico

What is the cheapest month to book a flight from New Windsor to Puerto Rico?

Currently, February is the cheapest month in which you can book a flight from New Windsor to Puerto Rico (average of $52). Flying from New Windsor to Puerto Rico 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 Puerto Rico. 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 Puerto Rico?

    If you book a flight to Puerto Rico 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.

  • Can I find deals for flights from Stewart to Puerto Rico that include hotel bookings?

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

  • How can I find direct flights from Stewart to Puerto Rico?

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

  • Can I find deals for business class flights from Stewart to Puerto Rico?

    Yes. Cheapflights offers flight deals from Stewart to Puerto Rico 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 Puerto Rico?

    Currently, February is the cheapest month in which you can book a flight from New Windsor to Puerto Rico (average of $52). Flying from New Windsor to Puerto Rico 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 Puerto Rico

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