In terms of precipitation, rainfall in San José ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit San José when rainfall is around 0.0 in.

If weather is an important factor for your trip to San José, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

What is the cheapest time of day to fly from SWF to SJO?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to San José as you normally would.

Most accurate provider : When it comes to deals on New Windsor-San José flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-San José flight deals on Cheapflights vs. Expedia 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 Expedia the most. Expedia 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.

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.

$162+ Flights from New Windsor to San José

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Cheap 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 20, 2026.

Thu 2/2611:52 am

SWF

SJO

1 stop25h 30m

Multiple Airlines

Thu 3/512:35 pm

SJO

SWF

2 stops21h 56m

Multiple Airlines

Deal found 1/18

$344

Sun 1/2512:13 pm

SWF

SJO

2 stops31h 42m

Multiple Airlines

Sun 2/11:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/18

$393

Mon 1/267:33 pm

SWF

SJO

1 stop17h 04m

Multiple Airlines

Sun 2/11:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/20

$493

Fri 1/3011:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/11:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/18

$738

Fri 2/611:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/81:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/20

$763

Fri 1/2311:09 am

SWF

SJO

2 stops25h 28m

Multiple Airlines

Sun 1/251:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/19

$822

Fri 1/3011:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/81:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/19

$932

Best flights from Stewart to San José
Discover carefully curated flight deals from Stewart to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 20, 2026.

Thu 2/2611:52 am

SWF

SJO

1 stop25h 30m

Multiple Airlines

Thu 3/512:35 pm

SJO

SWF

2 stops21h 56m

Multiple Airlines

Deal found 1/18

$344

Fri 1/3011:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/11:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/18

$738

Fri 2/611:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/81:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/20

$763

Fri 1/3011:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/81:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/19

$932

Last-minute flights from Stewart to San José
Discover last-minute flight deals from Stewart to San José. Data last updated January 20, 2026 and is based on user searches.

Fri 1/2311:09 am

SWF

SJO

2 stops25h 28m

Multiple Airlines

Sun 1/251:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/19

$822

Sun 1/2512:13 pm

SWF

SJO

2 stops31h 42m

Multiple Airlines

Sun 2/11:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/18

$393

Mon 1/267:33 pm

SWF

SJO

1 stop17h 04m

Multiple Airlines

Sun 2/11:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/20

$493

Fri 1/3011:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/11:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/18

$738

Fri 1/3011:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/81:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/19

$932

Fri 2/611:09 am

SWF

SJO

2 stops11h 43m

Multiple Airlines

Sun 2/81:30 pm

SJO

SWF

1 stop19h 49m

Multiple Airlines

Deal found 1/20

$763

Thu 2/2611:52 am

SWF

SJO

1 stop25h 30m

Multiple Airlines

Thu 3/512:35 pm

SJO

SWF

2 stops21h 56m

Multiple Airlines

Deal found 1/18

$344

One-way flights from Stewart to San José
Search for one-way flight options from Stewart to San José. Find affordable one-way fares based on user searches. Data last updated January 20, 2026.

Sun 3/111:52 am

SWF

SJO

1 stop25h 30m

Multiple Airlines

Deal found 1/17

$162

Sun 3/1512:29 pm

SWF

SJO

1 stop24h 50m

Multiple Airlines

Deal found 1/18

$175

Sun 3/810:09 am

SWF

SJO

1 stop27h 13m

Multiple Airlines

Deal found 1/19

$182

Sun 3/2210:29 am

SWF

SJO

1 stop26h 50m

Multiple Airlines

Deal found 1/19

$188

Mon 3/212:11 pm

SWF

SJO

2 stops24h 29m

Multiple Airlines

Deal found 1/19

$202

Mon 3/912:11 pm

SWF

SJO

2 stops24h 29m

Multiple Airlines

Deal found 1/18

$205

Mon 3/1612:11 pm

SWF

SJO

2 stops24h 31m

Multiple Airlines

Deal found 1/20

$210

Find flight deals from Stewart to San José

Most accurate provider	Expedia 2 stars
Most trusted provider	Expedia 3 stars
Round-trip from	$344 (Kiwi.com)
One-way from	$162 (Kiwi.com)
Popular in	December
Cheapest in	October
Average price	$430

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. 5% potential increase in price ($27 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in January 2026

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 2/26

11:52 am-12:22 pm

1 stop25h 30m

San José Juan Santamaria Intl

Thu 3/5

12:35 pm-11:31 am

2 stops21h 56m

$344

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 1/30

11:09 am-9:52 pm

2 stops11h 43m

San José Juan Santamaria Intl

Sun 2/1

1:30 pm-10:19 am

1 stop19h 49m

$738

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 2/6

11:09 am-9:52 pm

2 stops11h 43m

San José Juan Santamaria Intl

Sun 2/8

1:30 pm-10:19 am

1 stop19h 49m

$763

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 1/30

11:09 am-9:52 pm

2 stops11h 43m

San José Juan Santamaria Intl

Sun 2/8

1:30 pm-10:19 am

1 stop19h 49m

$932

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 3/1

11:52 am-12:22 pm

1 stop25h 30m

$162

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 3/15

12:29 pm-11:19 am

1 stop24h 50m

$175

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 3/8

10:09 am-11:22 am

1 stop27h 13m

$182

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 3/22

10:29 am-11:19 am

1 stop26h 50m

$188

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 3/2

12:11 pm-11:40 am

2 stops24h 29m

$202

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 3/16

12:11 pm-10:42 am

2 stops24h 31m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/17

Most accurate provider: When it comes to deals on New Windsor-San José flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-San José flight deals on Cheapflights vs. Expedia 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 Expedia the most. Expedia 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

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

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$162+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to San José with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to San José

Cheapest flights from Stewart to San JoséExplore 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 20, 2026.

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 20, 2026.

Find flight deals from Stewart to San José

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to San José that are best for you.

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.

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?

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?

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

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

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

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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 20, 2026.