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San José

$139+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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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 November 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/812:27 pmSWF - SJO
1 stop24h 58mMultiple Airlines
Sun 12/141:31 pmSJO - SWF
1 stop21h 06mMultiple Airlines
Deal found 11/11$333
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/1212:27 pmSWF - SJO
1 stop24h 58mMultiple Airlines
Sun 12/141:31 pmSJO - SWF
1 stop21h 06mMultiple Airlines
Deal found 11/11$341
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/812:27 pmSWF - SJO
1 stop24h 58mMultiple Airlines
Thu 12/181:31 pmSJO - SWF
1 stop27h 35mMultiple Airlines
Deal found 11/11$349
This Mytrip deal was found by Cheapflights users on 11/12. 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 11/1712:01 pmSWF - SJO
2 stops24h 38mMultiple Airlines
Thu 11/2011:24 amSJO - SWF
2 stops21h 58mMultiple Airlines
Deal found 11/12$355
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/1212:27 pmSWF - SJO
1 stop24h 58mMultiple Airlines
Thu 12/181:31 pmSJO - SWF
1 stop27h 35mMultiple Airlines
Deal found 11/11$356
This Mytrip deal was found by Cheapflights users on 11/11. 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 11/1411:01 amSWF - SJO
2 stops25h 38mMultiple Airlines
Thu 11/2011:24 amSJO - SWF
2 stops21h 58mMultiple Airlines
Deal found 11/11$372
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/1111:43 amSWF - SJO
1 stop24h 59mMultiple Airlines
Sun 12/141:31 pmSJO - SWF
1 stop21h 06mMultiple Airlines
Deal found 11/11$382
This Mytrip deal was found by Cheapflights users on 11/11. 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 11/1411:01 amSWF - SJO
2 stops25h 38mMultiple Airlines
Sun 11/2311:24 amSJO - SWF
2 stops21h 43mMultiple Airlines
Deal found 11/11$394
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/1111:43 amSWF - SJO
1 stop24h 59mMultiple Airlines
Thu 12/181:31 pmSJO - SWF
1 stop27h 35mMultiple Airlines
Deal found 11/11$397
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/812:27 pmSWF - SJO
1 stop24h 58mMultiple Airlines
Tue 12/161:31 pmSJO - SWF
2 stops43h 48mMultiple Airlines
Deal found 11/11$407

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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$333
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$379
Provider with most accurate pricing for New Windsor Stewart-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-San José Juan Santamaria Intl flights.
Search Deals
From New Windsor Stewart to San José Juan Santamaria Intl
Search Deals
One-way flight from New Windsor Stewart to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 12, 2025.
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 12/8

12:27 pm-12:25 pm

1 stop24h 58m

San José Juan Santamaria Intl

Sun 12/14

1:31 pm-11:37 am

1 stop21h 06m

$333

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 12/12

12:27 pm-12:25 pm

1 stop24h 58m

San José Juan Santamaria Intl

Sun 12/14

1:31 pm-11:37 am

1 stop21h 06m

$341

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/8

12:27 pm-12:25 pm

1 stop24h 58m

San José Juan Santamaria Intl

Thu 12/18

1:31 pm-6:06 pm

1 stop27h 35m

$349

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 12/12

12:27 pm-12:25 pm

1 stop24h 58m

San José Juan Santamaria Intl

Thu 12/18

1:31 pm-6:06 pm

1 stop27h 35m

$356

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 12/11

11:43 am-11:42 am

1 stop24h 59m

San José Juan Santamaria Intl

Thu 12/18

1:31 pm-6:06 pm

1 stop27h 35m

$397

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 1/23

11:09 am-11:37 am

2 stops25h 28m

San José Juan Santamaria Intl

Sun 1/25

12:33 pm-10:19 am

2 stops20h 46m

$403

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/8

12:27 pm-12:25 pm

1 stop24h 58m

San José Juan Santamaria Intl

Tue 12/16

1:31 pm-10:19 am

2 stops43h 48m

$407

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 12/5

7:30 pm-11:42 am

1 stop17h 12m

San José Juan Santamaria Intl

Sun 12/14

1:31 pm-11:37 am

1 stop21h 06m

$433

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 12/7

11:43 am-11:42 am

1 stop24h 59m

San José Juan Santamaria Intl

Thu 12/18

1:31 pm-6:06 pm

1 stop27h 35m

$436

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/8

12:27 pm-12:25 pm

1 stop24h 58m

San José Juan Santamaria Intl

Sat 12/13

12:39 pm-11:03 am

1 stop21h 24m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 20 results
1
2

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 November.
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
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó
Dominical

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