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 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.

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.

$169+ 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 December 23, 2025.

Mon 12/228:25 pmSWF - SJO

1 stop17h 00mMultiple Airlines

Thu 12/2512:39 pmSJO - SWF

2 stops21h 28mMultiple Airlines

Deal found 12/21

$748

Thu 12/2511:43 amSWF - SJO

1 stop24h 59mMultiple Airlines

Thu 1/81:30 pmSJO - SWF

1 stop19h 49mMultiple Airlines

Deal found 12/20

$770

Sun 12/2111:43 amSWF - SJO

1 stop24h 59mMultiple Airlines

Sun 12/281:31 pmSJO - SWF

1 stop20h 16mMultiple Airlines

Deal found 12/20

$890

Wed 12/245:34 pmSWF - SJO

1 stop19h 08mMultiple Airlines

Mon 12/2912:39 pmSJO - SWF

1 stop21h 24mMultiple Airlines

Deal found 12/20

$988

Tue 12/2311:43 amSWF - SJO

1 stop24h 59mMultiple Airlines

Mon 12/2912:39 pmSJO - SWF

1 stop21h 24mMultiple Airlines

Deal found 12/20

$1,015

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 December 23, 2025.

Sun 1/1812:13 pmSWF - SJO

2 stops25h 09mMultiple Airlines

Sun 1/251:30 pmSJO - SWF

1 stop19h 49mMultiple Airlines

Deal found 12/21

$440

Mon 1/127:33 pmSWF - SJO

1 stop17h 04mMultiple Airlines

Mon 1/197:22 amSJO - SWF

1 stop10h 21mMultiple Airlines

Deal found 12/21

$525

Thu 12/2511:43 amSWF - SJO

1 stop24h 59mMultiple Airlines

Thu 1/81:30 pmSJO - SWF

1 stop19h 49mMultiple Airlines

Deal found 12/20

$770

Last-minute flights from Stewart to San José
Discover last-minute flight deals from Stewart to San José. Data last updated December 23, 2025 and is based on user searches.

Mon 12/228:25 pmSWF - SJO

1 stop17h 00mMultiple Airlines

Thu 12/2512:39 pmSJO - SWF

2 stops21h 28mMultiple Airlines

Deal found 12/21

$748

Tue 12/2311:43 amSWF - SJO

1 stop24h 59mMultiple Airlines

Mon 12/2912:39 pmSJO - SWF

1 stop21h 24mMultiple Airlines

Deal found 12/20

$1,015

Wed 12/245:34 pmSWF - SJO

1 stop19h 08mMultiple Airlines

Mon 12/2912:39 pmSJO - SWF

1 stop21h 24mMultiple Airlines

Deal found 12/20

$988

Thu 12/2511:43 amSWF - SJO

1 stop24h 59mMultiple Airlines

Thu 1/81:30 pmSJO - SWF

1 stop19h 49mMultiple Airlines

Deal found 12/20

$770

Mon 1/127:33 pmSWF - SJO

1 stop17h 04mMultiple Airlines

Mon 1/197:22 amSJO - SWF

1 stop10h 21mMultiple Airlines

Deal found 12/21

$525

Sun 1/1812:13 pmSWF - SJO

2 stops25h 09mMultiple Airlines

Sun 1/251:30 pmSJO - SWF

1 stop19h 49mMultiple Airlines

Deal found 12/21

$440

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 December 23, 2025.

Mon 1/511:37 amSWF - SJO

1 stop25h 48mMultiple Airlines

Deal found 12/21

$169

Mon 1/127:33 pmSWF - SJO

1 stop17h 04mMultiple Airlines

Deal found 12/22

$173

Mon 1/197:33 pmSWF - SJO

1 stop17h 04mMultiple Airlines

Deal found 12/20

$178

Fri 1/97:33 pmSWF - SJO

1 stop17h 04mMultiple Airlines

Deal found 12/19

$191

Sat 1/38:45 pmSWF - SJO

2 stops16h 40mMultiple Airlines

Deal found 12/21

$351

Thu 2/1211:42 amSWF - SJO

2 stops23h 18mMultiple Airlines

Deal found 12/20

$439

Mon 12/2912:52 pmSWF - SJO

1 stop23h 50mMultiple Airlines

Deal found 12/21

$443

Thu 12/2511:43 amSWF - SJO

1 stop24h 59mMultiple Airlines

Deal found 12/21

$509

Find flight deals from Stewart to San José

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$440 (Kiwi.com)
One-way from	$169 (Kiwi.com)
Popular in	December
Cheapest in	October
Average price	$657

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. 6% potential increase in price ($32 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

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

Sun 1/18

12:13 pm-12:22 pm

2 stops25h 09m

San José Juan Santamaria Intl

Sun 1/25

1:30 pm-10:19 am

1 stop19h 49m

$440

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

$525

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 12/25

11:43 am-11:42 am

1 stop24h 59m

San José Juan Santamaria Intl

Thu 1/8

1:30 pm-10:19 am

1 stop19h 49m

$770

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/5

11:37 am-12:25 pm

1 stop25h 48m

$169

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/12

7:33 pm-11:37 am

1 stop17h 04m

$173

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/19

7:33 pm-11:37 am

1 stop17h 04m

$178

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 1/9

7:33 pm-11:37 am

1 stop17h 04m

$191

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sat 1/3

8:45 pm-12:25 pm

2 stops16h 40m

$351

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/29

12:52 pm-11:42 am

1 stop23h 50m

$443

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Compare providers for flights from Stewart to San José

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 December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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, December is the cheapest month in which you can book a flight from New Windsor to San José (average of $168). 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, December is the cheapest month in which you can book a flight from New Windsor to San José (average of $168). 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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Alajuela

Monteverde

Jacó

Heredia

Dominical

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$169+ 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 1/5. 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 December 23, 2025.

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 December 23, 2025.

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.

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 December.

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 December 23, 2025.