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Puerto Rico

$144+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
feb. 19 — feb. 261
jue. 2/19
jue. 2/26
1 adult, Economy
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Cheap 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 enero 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
lun. 1/267:33 pm
SWF
-
SJU
1 stop13h 14m
Multiple Airlines
vie. 1/308:00 am
SJU
-
SWF
1 stop11h 43m
Multiple Airlines
Deal found 1/20$288
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
lun. 3/239:47 am
SWF
-
SJU
1 stop12h 16m
Multiple Airlines
mié. 3/256:30 am
SJU
-
SWF
1 stop28h 38m
Multiple Airlines
Deal found 1/19$304
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
lun. 3/239:47 am
SWF
-
SJU
1 stop12h 16m
Multiple Airlines
vie. 3/273:19 pm
SJU
-
SWF
1 stop19h 19m
Multiple Airlines
Deal found 1/19$324
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
vie. 5/811:40 am
SWF
-
SJU
1 stop21h 07m
Multiple Airlines
jue. 5/147:05 pm
SJU
-
SWF
1 stop15h 45m
Multiple Airlines
Deal found 1/19$332
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
vie. 5/111:40 am
SWF
-
SJU
1 stop21h 07m
Multiple Airlines
sáb. 5/97:05 pm
SJU
-
SWF
1 stop13h 53m
Multiple Airlines
Deal found 1/19$337
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
dom. 3/2211:48 am
SWF
-
SJU
1 stop21h 05m
Multiple Airlines
mié. 3/256:30 am
SJU
-
SWF
1 stop28h 38m
Multiple Airlines
Deal found 1/19$338
This Kiwi.com deal was found by Cheapflights users on 1/19. 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. 3/1911:48 am
SWF
-
SJU
1 stop10h 15m
Multiple Airlines
mié. 3/256:30 am
SJU
-
SWF
1 stop28h 38m
Multiple Airlines
Deal found 1/19$349
This Kiwi.com deal was found by Cheapflights users on 1/19. 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. 3/1911:48 am
SWF
-
SJU
1 stop10h 15m
Multiple Airlines
mié. 3/251:45 am
SJU
-
SWF
1 stop9h 23m
Multiple Airlines
Deal found 1/19$350
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
dom. 2/811:48 am
SWF
-
SJU
1 stop10h 45m
Multiple Airlines
vie. 2/137:44 pm
SJU
-
SWF
2 stops40h 08m
Multiple Airlines
Deal found 1/20$353
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
vie. 3/612:11 pm
SWF
-
SJU
2 stops9h 58m
Multiple Airlines
sáb. 3/143:22 pm
SJU
-
SWF
1 stop20h 17m
Multiple Airlines
Deal found 1/18$354
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
dom. 2/2211:48 am
SWF
-
BQN
1 stop14h 09m
Multiple Airlines
vie. 2/273:58 am
BQN
-
SWF
2 stops32h 04m
Multiple Airlines
Deal found 1/18$443
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
vie. 2/2011:04 am
SWF
-
BQN
1 stop14h 53m
Multiple Airlines
sáb. 2/213:58 am
BQN
-
SWF
1 stop8h 10m
Multiple Airlines
Deal found 1/19$543

Find 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 enero 20, 2026.

Round-trip from

$304
(Kiwi.com)

One-way from

$144
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$241
From New Windsor Stewart to Puerto Rico
Search Deals
One-way flight from New Windsor Stewart to Puerto Rico
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 enero 20, 2026.
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

vie. 3/6

12:11 pm-11:09 pm

2 stops9h 58m

San Juan Luis Munoz Marin Intl

sáb. 3/14

3:22 pm-11:39 am

1 stop20h 17m

$354

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

vie. 3/20

9:42 am-8:53 am

1 stop23h 11m

San Juan Luis Munoz Marin Intl

mié. 3/25

7:00 am-9:39 am

2 stops26h 39m

$378

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

dom. 2/22

11:48 am-2:57 am

1 stop14h 09m

Aguadilla Borinquen

vie. 2/27

3:58 am-11:02 am

2 stops32h 04m

$443

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

vie. 3/6

12:11 pm-10:47 pm

2 stops9h 36m

San Juan Luis Munoz Marin Intl

sáb. 3/14

1:45 am-11:08 am

1 stop9h 23m

$477

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 2/1

12:13 pm-1:08 am

1 stop11h 55m

San Juan Luis Munoz Marin Intl

sáb. 2/7

8:05 pm-11:08 am

1 stop16h 03m

$493

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 3/1

11:48 am-2:53 am

1 stop14h 05m

San Juan Luis Munoz Marin Intl

mié. 3/4

8:05 pm-11:08 am

1 stop16h 03m

$499

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 3/1

11:48 am-2:53 am

1 stop14h 05m

San Juan Luis Munoz Marin Intl

mié. 3/4

3:53 am-11:08 am

1 stop8h 15m

$499

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

jue. 2/26

11:48 am-2:53 am

1 stop14h 05m

San Juan Luis Munoz Marin Intl

mié. 3/4

8:05 pm-11:08 am

1 stop16h 03m

$510

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

jue. 3/5

11:48 am-11:09 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

mié. 3/11

7:05 pm-11:08 am

1 stop16h 03m

$515

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

dom. 3/8

11:48 am-10:09 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

mié. 3/11

7:05 pm-11:08 am

1 stop16h 03m

$515

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 36 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, March is the cheapest month in which you can book a flight from New Windsor to Puerto Rico (average of $62). 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.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated enero 20, 2026.
Get a feel of what it's like to fly with JetBlue from New Windsor to Puerto Rico by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,892 reviews

Overall

7.2

Crew

8.0

Food

6.6

Entertainment

7.2

Boarding

7.4

Comfort

7.5

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
JetBlue
7.2
Good
2,892 reviews
JetBlue
7.2
Good
2,892 reviews

Overall

7.2

Crew

8.0

Food

6.6

Entertainment

7.2

Boarding

7.4

Comfort

7.5

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.

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, March is the cheapest month in which you can book a flight from New Windsor to Puerto Rico (average of $62). 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

Browse thousands of different options on Cheapflights for your next trip

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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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Top airline flying from Stewart to Puerto Rico

Discover the top airline that operate flights from Stewart to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated enero 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$244Average$336FlexibilityNo cancel feeOn-time62%

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