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San José

$137+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
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 noviembre 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/25. 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
1 stop24h 58mMultiple Airlines
mié. 12/311:24 amSJO - SWF
1 stop22h 39mMultiple Airlines
Deal found 11/25$531
This Mytrip deal was found by Cheapflights users on 11/25. 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.
lun. 12/157:30 pmSWF - SJO
1 stop17h 12mMultiple Airlines
lun. 12/227:22 amSJO - SWF
1 stop9h 58mMultiple Airlines
Deal found 11/25$622
This Mytrip deal was found by Cheapflights users on 11/25. 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.
lun. 12/228:25 pmSWF - SJO
1 stop17h 00mMultiple Airlines
dom. 12/2812:39 pmSJO - SWF
2 stops21h 08mMultiple Airlines
Deal found 11/25$630
This Mytrip deal was found by Cheapflights users on 11/24. 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.
lun. 12/157:30 pmSWF - SJO
1 stop17h 12mMultiple Airlines
vie. 1/97:22 amSJO - SWF
1 stop10h 21mMultiple Airlines
Deal found 11/24$642
This Mytrip deal was found by Cheapflights users on 11/24. 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.
vie. 12/196:56 pmSWF - SJO
3 stops41h 46mMultiple Airlines
dom. 12/287:22 amSJO - SWF
2 stops26h 25mMultiple Airlines
Deal found 11/24$762
This Mytrip deal was found by Cheapflights users on 11/25. 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.
sáb. 12/209:45 amSWF - SJO
3 stops27h 40mMultiple Airlines
dom. 12/2812:39 pmSJO - SWF
2 stops21h 08mMultiple Airlines
Deal found 11/25$775

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 noviembre 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$342
(Mytrip)

One-way from

$137
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$377
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.
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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. 8% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 noviembre 26, 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. 1/9

11:09 am-11:37 am

2 stops25h 28m

San José Juan Santamaria Intl

dom. 1/18

12:33 pm-10:19 am

2 stops20h 46m

$460

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

lun. 1/12

7:33 pm-11:37 am

1 stop17h 04m

San José Juan Santamaria Intl

lun. 1/19

7:22 am-6:43 pm

1 stop10h 21m

$533

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

lun. 12/15

7:30 pm-11:42 am

1 stop17h 12m

San José Juan Santamaria Intl

lun. 12/22

7:22 am-6:20 pm

1 stop9h 58m

$622

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

lun. 12/22

8:25 pm-12:25 pm

1 stop17h 00m

San José Juan Santamaria Intl

dom. 12/28

12:39 pm-10:47 am

2 stops21h 08m

$630

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

lun. 12/15

7:30 pm-11:42 am

1 stop17h 12m

San José Juan Santamaria Intl

vie. 1/9

7:22 am-6:43 pm

1 stop10h 21m

$642

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 12/19

6:56 pm-11:42 am

3 stops41h 46m

San José Juan Santamaria Intl

dom. 12/28

7:22 am-10:47 am

2 stops26h 25m

$762

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

sáb. 12/20

9:45 am-12:25 pm

3 stops27h 40m

San José Juan Santamaria Intl

dom. 12/28

12:39 pm-10:47 am

2 stops21h 08m

$775

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 12/19

6:56 pm-11:42 am

2 stops17h 46m

San José Juan Santamaria Intl

jue. 12/25

12:39 pm-11:07 am

2 stops21h 28m

$902

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

lun. 2/9

11:09 am-12:22 pm

1 stop26h 13m

$137

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

vie. 12/12

7:30 pm-11:42 am

1 stop17h 12m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 16 results
1
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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 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 $178). 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 $178). 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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