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Cheap flights from New Windsor (SWF) to San José (SJO)

SWF — SJO
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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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

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3. Compare prices and book

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Find flight deals from Stewart to San José

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to San José (SJO). 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 February 20, 2026.

Most accurate provider

Ovago
2 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$970
(Kiwi.com)

One-way from

$151
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$479
Provider with most accurate pricing for New Windsor Stewart-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-San José Juan Santamaria Intl flights.
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From New Windsor Stewart to San José Juan Santamaria Intl
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One-way flight from New Windsor Stewart to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 6% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
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Compare providers for flights from Stewart to San José

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to San José in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-San José flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on New Windsor-San José flight deals on Cheapflights vs. Ovago 90-95% of the time. Price accuracy is based on data collected from New Windsor-San José flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-San José flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-San José flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to San José

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

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

Currently, October is the cheapest month in which you can book a flight from New Windsor to San José (average of $176). Flying from New Windsor to San José in June is currently the most expensive (average of $272). 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 San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from New Windsor to San José (average of $176). Flying from New Windsor to San José in June is currently the most expensive (average of $272). 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

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Alajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio

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