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$151+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$365
(Kiwi.com)

One-way from

$151
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$328
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. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/1111:43 amSWF - BQN
1 stop14h 44mMultiple Airlines
Sat 9/133:32 amBQN - SWF
1 stop7h 31mMultiple Airlines
Deal found 8/11$365
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 8/217:52 pmSWF - BQN
1 stop30h 52mMultiple Airlines
Mon 8/253:43 amBQN - SWF
1 stop8h 13mMultiple Airlines
Deal found 8/11$438
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 8/2412:13 pmSWF - SJU
1 stop11h 50mMultiple Airlines
Sat 8/306:55 pmSJU - SWF
1 stop16h 28mMultiple Airlines
Deal found 8/13$490
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Fri 8/221:28 pmSWF - BQN
2 stops13h 16mMultiple Airlines
Wed 8/273:43 amBQN - SWF
1 stop15h 29mMultiple Airlines
Deal found 8/11$492
This Mytrip deal was found by Cheapflights users on 8/14. 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 8/225:36 pmSWF - SJU
2 stops21h 34mMultiple Airlines
Sun 8/244:12 pmSJU - SWF
2 stops24h 34mMultiple Airlines
Deal found 8/14$497
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 8/2112:13 pmSWF - SJU
1 stop11h 50mMultiple Airlines
Mon 8/259:00 amSJU - SWF
1 stop7h 46mMultiple Airlines
Deal found 8/13$503
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Fri 10/312:24 pmSWF - SJU
2 stops11h 35mMultiple Airlines
Sat 10/43:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Deal found 8/13$537
This Mytrip deal was found by Cheapflights users on 8/14. 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 8/291:55 pmSWF - SJU
1 stop7h 53mMultiple Airlines
Sun 8/312:11 amSJU - SWF
2 stops10h 54mMultiple Airlines
Deal found 8/14$544
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 8/2612:36 pmSWF - SJU
1 stop11h 21mMultiple Airlines
Wed 9/33:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Deal found 8/12$570
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Fri 8/291:55 pmSWF - SJU
1 stop7h 53mMultiple Airlines
Sun 8/318:13 pmSJU - SWF
1 stop13h 59mMultiple Airlines
Deal found 8/14$572
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Fri 9/1912:24 pmSWF - SJU
2 stops11h 35mMultiple Airlines
Wed 9/243:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Deal found 8/13$590
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/1611:43 amSWF - SJU
1 stop14h 01mMultiple Airlines
Sat 10/182:49 amSJU - SWF
1 stop8h 14mMultiple Airlines
Deal found 8/14$594

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 August 14, 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 WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 9/11

11:43 am-2:27 am

1 stop14h 44m

Aguadilla Borinquen

Sat 9/13

3:32 am-11:03 am

1 stop7h 31m

$365

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 10/26

5:45 pm-1:43 am

3 stops31h 58m

San Juan Luis Munoz Marin Intl

Wed 10/29

3:19 pm-12:45 pm

3 stops21h 26m

$484

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 8/24

12:13 pm-12:03 am

1 stop11h 50m

San Juan Luis Munoz Marin Intl

Sat 8/30

6:55 pm-11:23 am

1 stop16h 28m

$490

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 8/29

1:55 pm-9:48 pm

1 stop7h 53m

San Juan Luis Munoz Marin Intl

Sat 8/30

3:59 am-7:12 pm

1 stop15h 13m

$496

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 8/25

5:36 pm-4:42 pm

2 stops23h 06m

San Juan Luis Munoz Marin Intl

Sun 8/31

2:11 am-1:05 pm

2 stops10h 54m

$525

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 8/29

1:55 pm-9:48 pm

1 stop7h 53m

San Juan Luis Munoz Marin Intl

Mon 9/1

3:55 am-11:56 am

1 stop8h 01m

$530

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 10/3

12:24 pm-11:59 pm

2 stops11h 35m

San Juan Luis Munoz Marin Intl

Sat 10/4

3:39 am-11:03 am

1 stop7h 24m

$537

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 8/28

7:52 pm-8:59 am

1 stop13h 07m

San Juan Luis Munoz Marin Intl

Sat 8/30

3:59 am-7:12 pm

1 stop15h 13m

$558

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Tue 8/26

12:36 pm-11:57 pm

1 stop11h 21m

San Juan Luis Munoz Marin Intl

Wed 9/3

3:39 am-11:03 am

1 stop7h 24m

$570

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 2/6

11:09 am-10:59 pm

1 stop10h 50m

San Juan Luis Munoz Marin Intl

Wed 2/11

8:28 pm-11:08 am

1 stop15h 40m

$571

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 20 results
1
2

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, September is the cheapest month in which you can book a flight from New Windsor to Puerto Rico (average of $254). Flying from New Windsor to Puerto Rico in June is currently the most expensive (average of $339). 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 August 14, 2025.
Get a feel of what it's like to fly with JetBlue and Frontier 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
2,913 reviews

Boarding

7.4

Entertainment

7.3

Overall

7.2

Comfort

7.6

Food

6.7

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
JetBlue
7.2
Good
2,913 reviews
JetBlue
7.2
Good
2,913 reviews

Boarding

7.4

Entertainment

7.3

Overall

7.2

Comfort

7.6

Food

6.7

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
Frontier
5.8
Fair
3,217 reviews
JetBlue
7.2
Good
2,913 reviews

Boarding

7.4

Entertainment

7.3

Overall

7.2

Comfort

7.6

Food

6.7

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.

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, September is the cheapest month in which you can book a flight from New Windsor to Puerto Rico (average of $254). Flying from New Windsor to Puerto Rico in June is currently the most expensive (average of $339). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Stewart to Puerto Rico

Discover the top 2 airlines 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$166FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$244Average$336FlexibilityNo cancel feeOn-time62%

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