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$123+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 July 2, 2025.

Round-trip from

$316
(Mytrip)

One-way from

$123
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$293
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. 9% potential increase in price ($27 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 July 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 July 2, 2025.

This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/255:36 pmSWF - SJU
2 stops21h 34mMultiple Airlines
Thu 8/2810:10 amSJU - SWF
2 stops26h 55mMultiple Airlines
Deal found 7/2$312

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 July 2, 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

Mon 8/25

5:36 pm-3:10 pm

2 stops21h 34m

San Juan Luis Munoz Marin Intl

Thu 8/28

10:10 am-1:05 pm

2 stops26h 55m

$312

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 8/15

7:37 pm-3:10 pm

2 stops19h 33m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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.

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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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 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$186FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$175Average$338FlexibilityNo cancel feeOn-time62%

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