HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$174+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Nov 14 — Nov 211
Fri 11/14
Fri 11/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Puerto Rico with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 15, 2025.

Round-trip from

$352
(Kiwi.com)

One-way from

$174
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$220
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. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Sun 10/267:11 pmSWF - SJU
1 stop28h 18mMultiple Airlines
Sat 11/13:04 amSJU - SWF
1 stop8h 59mMultiple Airlines
Deal found 10/14$352
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/308:41 pmSWF - SJU
1 stop29h 13mMultiple Airlines
Thu 12/49:32 pmSJU - SWF
1 stop22h 08mMultiple Airlines
Deal found 10/13$435
This Mytrip deal was found by Cheapflights users on 10/15. 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 11/2111:12 amSWF - SJU
1 stop8h 15mMultiple Airlines
Tue 11/256:00 amSJU - SWF
2 stops30h 27mMultiple Airlines
Deal found 10/15$455
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/306:16 pmSWF - SJU
1 stop19h 03mMultiple Airlines
Sat 11/13:04 amSJU - SWF
1 stop8h 59mMultiple Airlines
Deal found 10/15$479
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 11/2011:43 amSWF - SJU
1 stop8h 29mMultiple Airlines
Mon 11/249:45 pmSJU - SWF
1 stop12h 08mMultiple Airlines
Deal found 10/14$482
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 10/1611:43 amSWF - SJU
1 stop14h 01mMultiple Airlines
Thu 10/2311:51 amSJU - SWF
1 stop22h 50mMultiple Airlines
Deal found 10/13$502
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Sun 12/1411:43 amSWF - SJU
1 stop7h 44mMultiple Airlines
Fri 12/198:10 amSJU - SWF
1 stop10h 56mMultiple Airlines
Deal found 10/14$516
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Sun 10/2611:43 amSWF - SJU
1 stop14h 47mMultiple Airlines
Sat 11/19:25 pmSJU - SWF
2 stops38h 46mMultiple Airlines
Deal found 10/14$525
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/211:43 amSWF - BQN
1 stop14h 21mMultiple Airlines
Sat 11/84:25 pmBQN - SWF
1 stop19h 38mMultiple Airlines
Deal found 10/15$593
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 11/1412:24 pmSWF - BQN
2 stops13h 40mMultiple Airlines
Sat 11/223:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Deal found 10/14$634
This Kiwi.com deal was found by Cheapflights users on 10/15. 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
Wed 12/243:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Deal found 10/15$656
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/611:43 amSWF - BQN
1 stop14h 21mMultiple Airlines
Sat 11/83:59 amBQN - SWF
1 stop8h 04mMultiple Airlines
Deal found 10/13$683

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 October 15, 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 11/21

11:12 am-8:27 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Tue 11/25

11:54 am-11:27 am

2 stops24h 33m

$455

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 11/20

11:43 am-9:12 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Mon 11/24

9:45 pm-8:53 am

1 stop12h 08m

$482

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 12/14

11:43 am-8:27 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Fri 12/19

8:10 am-6:06 pm

1 stop10h 56m

$516

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 10/26

11:43 am-2:30 am

1 stop14h 47m

San Juan Luis Munoz Marin Intl

Sat 11/1

9:25 pm-12:11 pm

2 stops38h 46m

$525

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 2/26

11:52 am-10:59 pm

1 stop10h 07m

San Juan Luis Munoz Marin Intl

Sun 3/1

8:28 pm-10:13 am

1 stop14h 45m

$558

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Wed 12/24

5:34 pm-12:50 am

1 stop30h 16m

San Juan Luis Munoz Marin Intl

Tue 12/30

3:55 am-4:44 pm

1 stop13h 49m

$609

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 11/6

6:14 pm-12:01 pm

1 stop16h 47m

San Juan Luis Munoz Marin Intl

Wed 11/12

3:59 am-11:03 am

1 stop8h 04m

$613

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 1/23

12:11 pm-2:50 am

2 stops13h 39m

San Juan Luis Munoz Marin Intl

Sat 1/31

3:55 am-11:08 am

1 stop8h 13m

$613

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 11/13

11:43 am-9:24 pm

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Wed 11/19

3:59 am-11:03 am

1 stop8h 04m

$623

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 1/8

11:48 am-2:58 am

1 stop14h 10m

Aguadilla Borinquen

Sat 1/10

3:55 am-11:08 am

1 stop8h 13m

$624

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 42 results
1
2
3
...
5

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
John F Kennedy Intl to Punta Cana flights
LaGuardia to Luis Munoz Marin Intl flights
Newark to Punta Cana flights
Newark to Santo Domingo flights
Newark to Santiago de los Caballeros flights
Newark to Oranjestad flights
John F Kennedy Intl to Montego Bay flights
LaGuardia to Santo Domingo flights
LaGuardia to Punta Cana flights
Newark to Montego Bay flights
John F Kennedy Intl to Oranjestad flights
John F Kennedy Intl to Port of Spain flights
Newark to Simpson Bay flights
Newark to Nassau flights
John F Kennedy Intl to Simpson Bay flights
John F Kennedy Intl to Saint Thomas Island flights
LaGuardia to Montego Bay flights
John F Kennedy Intl to Kingston flights
LaGuardia to Oranjestad flights
LaGuardia to Santiago de los Caballeros flights
John F Kennedy Intl to Nassau flights
Newark to Providenciales flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to Providenciales flights
LaGuardia to Simpson Bay flights
John F Kennedy Intl to Willemstad flights
John F Kennedy Intl to Puerto Plata flights
John F Kennedy Intl to Aguadilla flights
John F Kennedy Intl to Castries flights
John F Kennedy Intl to Bridgetown flights
LaGuardia to Nassau flights
LaGuardia to Providenciales flights
John F Kennedy Intl to St. John's flights
LaGuardia to Saint Thomas Island flights
LaGuardia to Kingston flights
John F Kennedy Intl to St. George's flights
John F Kennedy Intl to Ponce flights
Newark to George Town flights
Newark to Kingston flights
John F Kennedy Intl to George Town flights
White Plains to Luis Munoz Marin Intl flights
Islip to Luis Munoz Marin Intl flights
LaGuardia to Willemstad flights
LaGuardia to George Town flights
LaGuardia to Bridgetown flights
Newark to Aguadilla flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights