HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Juan

$191+ Cheap flights from New Windsor (SWF) to San Juan

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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to San Juan 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 San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$370
(Kiwi.com)

One-way from

$191
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$246
From New Windsor Stewart to San Juan
Search Deals
One-way flight from New Windsor Stewart to San Juan
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Stewart to San Juan

Cheapest flights from Stewart to San Juan
Explore the most affordable flight options available from Stewart to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/2411:31 amSWF - SJU
2 stops26h 57mMultiple Airlines
Thu 10/3011:51 amSJU - SWF
1 stop22h 50mMultiple Airlines
Deal found 9/13$370
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2811:43 amSWF - SJU
2 stops28h 35mMultiple Airlines
Thu 10/211:59 amSJU - SWF
1 stop23h 22mMultiple Airlines
Deal found 9/13$400
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/2311:43 amSWF - SJU
1 stop14h 01mMultiple Airlines
Thu 10/3011:51 amSJU - SWF
1 stop22h 50mMultiple Airlines
Deal found 9/13$416
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 10/1311:01 amSWF - SJU
2 stops38h 43mMultiple Airlines
Wed 10/223:19 pmSJU - SWF
1 stop19h 44mMultiple Airlines
Deal found 9/14$429
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/2311:43 amSWF - SJU
1 stop14h 01mMultiple Airlines
Wed 10/293:19 pmSJU - SWF
1 stop19h 44mMultiple Airlines
Deal found 9/13$472

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to San Juan 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 September 15, 2025.
Use the filters below to find and compare flights from New Windsor to San Juan that are best for you.

Fly from

Stewart

Fly to

San Juan

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 10/24

11:31 am-2:28 pm

2 stops26h 57m

San Juan Luis Munoz Marin Intl

Thu 10/30

11:51 am-10:41 am

1 stop22h 50m

$370

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 9/28

11:43 am-4:18 pm

2 stops28h 35m

San Juan Luis Munoz Marin Intl

Thu 10/2

11:59 am-11:21 am

1 stop23h 22m

$400

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/23

11:43 am-1:44 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Thu 10/30

11:51 am-10:41 am

1 stop22h 50m

$416

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 10/13

11:01 am-1:44 am

3 stops38h 43m

San Juan Luis Munoz Marin Intl

Wed 10/22

3:19 pm-4:55 pm

3 stops25h 36m

$448

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/23

11:43 am-1:44 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Wed 10/29

3:19 pm-11:03 am

1 stop19h 44m

$472

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 11/20

11:06 am-11:09 pm

1 stop11h 03m

San Juan Luis Munoz Marin Intl

Sun 11/23

5:05 pm-10:07 am

1 stop18h 02m

$526

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 10/30

11:43 am-1:44 am

1 stop14h 01m

San Juan Luis Munoz Marin Intl

Sat 11/1

2:48 am-11:03 am

1 stop9h 15m

$560

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 11/3

12:01 pm-2:44 am

3 stops37h 43m

$191

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 11/14

11:01 am-4:23 pm

2 stops28h 22m

$195

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 10/13

11:01 am-1:44 am

3 stops38h 43m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 16 results
1
2

Best time to book a flight from Stewart to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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 San Juan

What is the cheapest month to book a flight from New Windsor to San Juan?

Currently, September is the cheapest month in which you can book a flight from New Windsor to San Juan (average of $254). Flying from New Windsor to San Juan 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 San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with JetBlue from New Windsor to San Juan to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,912 reviews

Food

6.7

Boarding

7.4

Comfort

7.6

Crew

8.0

Overall

7.2

Entertainment

7.3

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
2,912 reviews
JetBlue
7.2
Good
2,912 reviews

Food

6.7

Boarding

7.4

Comfort

7.6

Crew

8.0

Overall

7.2

Entertainment

7.3

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 San Juan. 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 San Juan?

    If you book a flight to San Juan 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. There are 0 flights from Stewart to San Juan per day from 1 airline.

  • What is the cheapest airline to fly from New Windsor to San Juan round-trip?

    Flying on JetBlue is currently your cheapest option to San Juan, with prices starting at $244.

  • Can I find deals for flights from Stewart to San Juan that include hotel bookings?

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

  • How can I find direct flights from Stewart to San Juan?

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

  • Can I find deals for business class flights from Stewart to San Juan?

    Yes. Cheapflights offers flight deals from Stewart to San Juan 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 San Juan?

    Currently, September is the cheapest month in which you can book a flight from New Windsor to San Juan (average of $254). Flying from New Windsor to San Juan 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

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 San Juan

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Aguadilla flights
White Plains to Luis Munoz Marin Intl flights
John F Kennedy Intl to Ponce flights
Islip to Luis Munoz Marin Intl flights
Buffalo to Luis Munoz Marin Intl flights
Syracuse to Luis Munoz Marin Intl flights
Rochester to Luis Munoz Marin Intl flights
LaGuardia to Aguadilla flights
Newark to Aguadilla flights
LaGuardia to Ponce flights
Newark to Ponce flights
Stewart to Luis Munoz Marin Intl flights
Albany to Luis Munoz Marin Intl flights
John F Kennedy Intl to Culebra flights
White Plains to Ponce flights
Newark to Vieques flights
John F Kennedy Intl to Mayagüez flights
Newark to Mayagüez flights
Newark to Culebra flights
John F Kennedy Intl to Vieques flights
Syracuse to Aguadilla flights
Ithaca to Luis Munoz Marin Intl flights
Buffalo to Aguadilla flights
Buffalo to Ponce flights
White Plains to Aguadilla flights
LaGuardia to Vieques flights
Rochester to Aguadilla flights
Syracuse to Vieques flights
Stewart to Aguadilla flights
Watertown to Luis Munoz Marin Intl flights
Buffalo to Vieques flights
Saranac Lake to Luis Munoz Marin Intl flights
Rochester to Ponce flights
Syracuse to Culebra flights
Ithaca to Vieques flights
Rochester to Vieques flights
Plattsburgh to Luis Munoz Marin Intl flights
Albany to Culebra flights
Niagara Falls to Luis Munoz Marin Intl flights

Top airline flying from Stewart to San Juan

Discover the top airline that operate flights from Stewart to San Juan. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$244Average$336FlexibilityNo cancel feeOn-time62%

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.