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$157+ Cheap flights from New Windsor (SWF) to San José (SJO)

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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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Cheap 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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$353
(Mytrip)

One-way from

$157
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$437
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 ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Stewart to San José

Cheapest flights from Stewart to San José
Explore the most affordable flight options available from Stewart to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

This Mytrip deal was found by Cheapflights users on 1/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/27:33 pmSWF - SJO
1 stop17h 04mMultiple Airlines
Mon 2/97:22 amSJO - SWF
1 stop10h 21mMultiple Airlines
Deal found 1/5$353
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/1112:13 pmSWF - SJO
1 stop24h 24mMultiple Airlines
Thu 1/151:30 pmSJO - SWF
1 stop19h 49mMultiple Airlines
Deal found 1/5$410
This Mytrip deal was found by Cheapflights users on 1/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/127:33 pmSWF - SJO
1 stop17h 04mMultiple Airlines
Mon 1/197:22 amSJO - SWF
1 stop10h 21mMultiple Airlines
Deal found 1/4$654
This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
Mon 1/511:37 amSWF - SJO
2 stops11h 15mMultiple Airlines
Thu 1/81:30 pmSJO - SWF
1 stop19h 49mMultiple Airlines
Deal found 1/4$847

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to San José 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 January 6, 2026.
Use the filters below to find and compare flights from New Windsor to San José that are best for you.

Fly from

Stewart

Fly to

San José

Route

Depart

Return

Price

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 2/2

7:33 pm-11:37 am

1 stop17h 04m

San José Juan Santamaria Intl

Mon 2/9

7:22 am-6:43 pm

1 stop10h 21m

$353

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 1/11

12:13 pm-11:37 am

1 stop24h 24m

San José Juan Santamaria Intl

Thu 1/15

1:30 pm-10:19 am

1 stop19h 49m

$410

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/12

7:33 pm-11:37 am

1 stop17h 04m

San José Juan Santamaria Intl

Mon 1/19

7:22 am-6:43 pm

1 stop10h 21m

$654

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/12

11:09 am-11:37 am

2 stops25h 28m

$157

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 1/11

12:13 pm-11:37 am

1 stop24h 24m

$201

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 1/16

11:09 am-12:22 pm

1 stop26h 13m

$217

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/26

11:09 am-11:37 am

2 stops25h 28m

$222

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 2/15

7:28 pm-12:22 pm

2 stops17h 54m

$254

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 3/5

10:09 am-11:40 am

2 stops26h 31m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-San José flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $177). 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 $177). 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
Manuel Antonio
Alajuela
Monteverde
Jacó
Heredia
Dominical

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