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Puerto Rico

$170+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
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 May 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 10/110:28 am
SWF
-
SJU
1 stop13h 10m
Multiple Airlines
Wed 10/75:12 pm
SJU
-
SWF
1 stop16h 06m
Multiple Airlines
Deal found 5/5$304
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Wed 7/2912:05 pm
SWF
-
SJU
2 stops12h 36m
Multiple Airlines
Wed 8/56:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 5/2$324
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sun 8/231:00 pm
SWF
-
SJU
1 stop26h 58m
Multiple Airlines
Sun 8/306:00 am
SJU
-
SWF
1 stop12h 41m
Multiple Airlines
Deal found 5/5$325
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sat 8/112:05 pm
SWF
-
SJU
2 stops19h 52m
Multiple Airlines
Wed 8/56:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 5/5$327
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Wed 7/812:05 pm
SWF
-
SJU
2 stops12h 36m
Multiple Airlines
Wed 8/56:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 5/4$348
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 8/211:45 am
SWF
-
SJU
1 stop12h 56m
Multiple Airlines
Wed 8/56:00 am
SJU
-
SWF
1 stop27h 38m
Multiple Airlines
Deal found 5/2$359
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Wed 9/212:05 pm
SWF
-
SJU
2 stops12h 18m
Multiple Airlines
Sat 9/59:24 am
SJU
-
SWF
1 stop23h 34m
Multiple Airlines
Deal found 5/4$372
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 9/311:13 am
SWF
-
SJU
1 stop13h 10m
Multiple Airlines
Thu 9/106:42 pm
SJU
-
SWF
1 stop15h 34m
Multiple Airlines
Deal found 5/5$375
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Tue 8/2511:48 am
SWF
-
SJU
1 stop11h 41m
Multiple Airlines
Sun 8/306:00 am
SJU
-
SWF
1 stop12h 41m
Multiple Airlines
Deal found 5/5$376
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Sat 8/1512:05 pm
SWF
-
SJU
1 stop28h 37m
Multiple Airlines
Sat 8/227:00 am
SJU
-
SWF
2 stops29h 10m
Multiple Airlines
Deal found 5/3$378
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Mon 8/1012:17 pm
SWF
-
BQN
2 stops13h 48m
Multiple Airlines
Fri 8/143:00 am
BQN
-
SWF
1 stop12h 50m
Multiple Airlines
Deal found 5/5$405
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 6/247:56 pm
SWF
-
BQN
1 stop15h 37m
Multiple Airlines
Tue 6/303:00 am
BQN
-
SWF
1 stop15h 56m
Multiple Airlines
Deal found 5/1$426

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 May 6, 2026.

Round-trip from

$304
(Kiwi.com)

One-way from

$170
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$302
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. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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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 May 6, 2026.
Use the filters below to find and compare flights from New Windsor to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Wed 6/24

7:56 pm-11:33 am

1 stop15h 37m

Aguadilla Borinquen

Tue 6/30

3:00 am-6:56 pm

1 stop15h 56m

$426

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Tue 8/4

11:48 am-11:29 pm

1 stop11h 41m

San Juan Luis Munoz Marin Intl

Wed 8/12

5:15 pm-9:38 am

2 stops16h 23m

$428

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 7/30

9:38 am-5:36 pm

1 stop7h 58m

San Juan Luis Munoz Marin Intl

Wed 8/5

6:00 am-9:38 am

1 stop27h 38m

$431

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 5/28

9:38 am-2:02 am

1 stop16h 24m

Aguadilla Borinquen

Sat 5/30

2:59 am-8:51 am

1 stop29h 52m

$431

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 5/17

9:38 am-2:02 am

1 stop16h 24m

Aguadilla Borinquen

Tue 6/9

3:00 am-8:58 am

1 stop29h 58m

$458

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 6/14

9:38 am-2:05 am

1 stop16h 27m

Aguadilla Borinquen

Sat 6/20

3:00 am-8:49 am

1 stop29h 49m

$458

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 7/30

10:28 am-2:16 pm

2 stops27h 48m

San Juan Luis Munoz Marin Intl

Mon 8/3

4:05 pm-11:08 am

1 stop19h 03m

$474

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 6/3

12:05 pm-4:01 am

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Sat 6/6

8:13 pm-8:58 am

1 stop12h 45m

$476

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Tue 7/28

11:48 am-2:11 am

1 stop14h 23m

San Juan Luis Munoz Marin Intl

Tue 8/4

6:45 pm-9:38 am

2 stops38h 53m

$485
Quickest round-trip

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 7/4

12:05 pm-12:37 am

2 stops12h 32m

San Juan Luis Munoz Marin Intl

Wed 7/8

6:31 pm-8:58 am

1 stop14h 27m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 42 resultsSorted by cheapest first
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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
No data available for this route at this time. Please check back soon.

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.

See more FAQs

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Alternative routes for Stewart to Puerto Rico

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