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San José

$129+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
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 septiembre 17, 2025.

Round-trip from

$314
(Kiwi.com)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$386
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. 10% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septiembre 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
vie. 12/512:27 pmSWF - SJO
1 stop24h 47mMultiple Airlines
dom. 12/71:16 amSJO - SWF
1 stop9h 21mMultiple Airlines
Deal found 9/15$314
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
mié. 11/2612:17 pmSWF - SJO
2 stops20h 16mMultiple Airlines
jue. 12/41:19 pmSJO - SWF
1 stop21h 18mMultiple Airlines
Deal found 9/16$366
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
dom. 11/308:41 pmSWF - SJO
1 stop15h 46mMultiple Airlines
dom. 12/71:19 pmSJO - SWF
1 stop21h 18mMultiple Airlines
Deal found 9/16$591
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
dom. 12/2111:43 amSWF - SJO
2 stops26h 53mMultiple Airlines
jue. 12/251:16 amSJO - SWF
1 stop8h 51mMultiple Airlines
Deal found 9/15$820
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
lun. 12/227:10 pmSWF - SJO
1 stop17h 17mMultiple Airlines
jue. 12/251:16 amSJO - SWF
1 stop8h 51mMultiple Airlines
Deal found 9/15$883
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
vie. 12/198:11 pmSWF - SJO
1 stop14h 10mMultiple Airlines
dom. 12/281:16 amSJO - SWF
1 stop8h 31mMultiple Airlines
Deal found 9/15$1,013
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
lun. 12/2911:37 amSWF - SJO
1 stop13h 44mMultiple Airlines
dom. 1/41:16 amSJO - SWF
1 stop8h 31mMultiple Airlines
Deal found 9/15$1,073
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
lun. 12/2911:37 amSWF - SJO
1 stop13h 44mMultiple Airlines
vie. 1/21:16 amSJO - SWF
2 stops17h 39mMultiple Airlines
Deal found 9/16$1,141
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
jue. 12/2511:43 amSWF - SJO
2 stops11h 13mMultiple Airlines
dom. 12/281:16 amSJO - SWF
1 stop8h 31mMultiple Airlines
Deal found 9/16$1,176

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 septiembre 17, 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

vie. 12/5

12:27 pm-12:14 pm

1 stop24h 47m

San José Juan Santamaria Intl

dom. 12/7

1:16 am-11:37 am

1 stop9h 21m

$314

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

mié. 11/26

12:17 pm-7:33 am

2 stops20h 16m

San José Juan Santamaria Intl

jue. 12/4

1:19 pm-11:37 am

1 stop21h 18m

$366

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

dom. 11/30

8:41 pm-11:27 am

1 stop15h 46m

San José Juan Santamaria Intl

dom. 12/7

1:19 pm-11:37 am

1 stop21h 18m

$591

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 10/31

11:31 am-10:41 am

2 stops25h 10m

$142

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 10/24

11:31 am-10:41 am

2 stops25h 10m

$146

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 10/17

11:31 am-10:41 am

2 stops25h 10m

$146

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

dom. 9/28

11:43 am-11:14 am

2 stops25h 31m

$159

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 12/5

12:27 pm-12:21 am

1 stop12h 54m

$167

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 10/10

11:41 am-11:30 am

1 stop25h 49m

$170

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

lun. 11/24

10:57 am-8:19 am

2 stops22h 22m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 11 results
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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, San José Province?

Currently, September is the cheapest month in which you can book a flight from New Windsor to San José, San José Province (average of $398). Flying from New Windsor to San José, San José Province in March is currently the most expensive (average of $554). 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, San José Province?

    Currently, September is the cheapest month in which you can book a flight from New Windsor to San José, San José Province (average of $398). Flying from New Windsor to San José, San José Province in March is currently the most expensive (average of $554). 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

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