HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San José

$133+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to San José with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Sat 12/209:45 amSWF - SJO
2 stops27h 40mMultiple Airlines
Thu 12/251:31 pmSJO - SWF
1 stop20h 36mMultiple Airlines
Deal found 12/17$698
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/228:25 pmSWF - SJO
2 stops16h 17mMultiple Airlines
Thu 12/251:31 pmSJO - SWF
1 stop20h 36mMultiple Airlines
Deal found 12/17$768
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Mon 12/2212:24 pmSWF - SJO
2 stops24h 18mMultiple Airlines
Mon 12/2912:39 pmSJO - SWF
1 stop21h 24mMultiple Airlines
Deal found 12/16$810
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Fri 12/1912:24 pmSWF - SJO
2 stops25h 01mMultiple Airlines
Mon 12/2912:39 pmSJO - SWF
1 stop21h 24mMultiple Airlines
Deal found 12/16$842
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/2511:43 amSWF - SJO
1 stop24h 59mMultiple Airlines
Tue 12/3012:39 pmSJO - SWF
1 stop27h 05mMultiple Airlines
Deal found 12/17$912
This Mytrip deal was found by Cheapflights users on 12/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - SJO
2 stops16h 17mMultiple Airlines
Sat 12/271:31 pmSJO - SWF
2 stops19h 28mMultiple Airlines
Deal found 12/15$970

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$329
(Mytrip)

One-way from

$133
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$653
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

 
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 December 18, 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 1/19

7:33 pm-11:37 am

1 stop17h 04m

San José Juan Santamaria Intl

Mon 1/26

7:22 am-6:43 pm

1 stop10h 21m

$329

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sat 12/20

9:45 am-12:25 pm

2 stops27h 40m

San José Juan Santamaria Intl

Thu 12/25

1:31 pm-11:07 am

1 stop20h 36m

$698

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/22

8:25 pm-11:42 am

2 stops16h 17m

San José Juan Santamaria Intl

Thu 12/25

1:31 pm-11:07 am

1 stop20h 36m

$768

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/22

12:24 pm-11:42 am

2 stops24h 18m

San José Juan Santamaria Intl

Mon 12/29

12:39 pm-11:03 am

1 stop21h 24m

$810

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/22

8:25 pm-12:25 pm

1 stop17h 00m

San José Juan Santamaria Intl

Sat 12/27

1:31 pm-9:59 am

2 stops19h 28m

$842

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

Tue 12/30

12:39 pm-4:44 pm

1 stop27h 05m

$912

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/12

11:09 am-12:22 pm

1 stop26h 13m

$133

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/26

11:09 am-11:37 am

2 stops25h 28m

$193

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 2/2

11:09 am-11:37 am

2 stops25h 28m

$197

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 2/15

11:42 am-12:22 pm

1 stop25h 40m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 13 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 December.
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, December is the cheapest month in which you can book a flight from New Windsor to San José (average of $166). 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, December is the cheapest month in which you can book a flight from New Windsor to San José (average of $166). 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
Manuel Antonio
Alajuela
Monteverde
Jacó
Heredia
Dominical

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to San José

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to San José flights
Newark to San José flights
John F Kennedy Intl to Liberia flights
Newark to Liberia flights
LaGuardia to San José flights
LaGuardia to Liberia flights
Syracuse to San José flights
Albany to San José flights
Buffalo to San José flights
Buffalo to Liberia flights
Syracuse to Liberia flights
Rochester to San José flights
Albany to Liberia flights
Rochester to Liberia flights
White Plains to San José flights
White Plains to Liberia flights
Islip to San José flights
Islip to Liberia flights
Ithaca to San José flights
Ithaca to Liberia flights
Elmira to San José flights
Binghamton to San José flights
Plattsburgh to San José flights
Watertown to Liberia flights
Binghamton to Liberia flights
Niagara Falls to San José flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.