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Stewart

$151+ Cheap flights from Costa Rica to New Windsor (SWF)

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — SWF
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
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Cheap flight deals from Costa Rica to Stewart

Keep the following information in mind while searching for Costa Rica to Stewart flight deals. Data was last updated October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$409
(Mytrip)

One-way from

$151
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$310
Provider with most accurate pricing for San José Juan Santamaria Intl-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-New York (NYC) flights.
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From Costa Rica to New Windsor Stewart
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One-way flight from Costa Rica to New Windsor Stewart
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Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Costa Rica to Stewart

Cheapest flights from Costa Rica to Stewart
Explore the most affordable flight options available from Costa Rica to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 13, 2025.

This Mytrip deal was found by Cheapflights users on 10/10. 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.
Thu 11/2011:24 amSJO - SWF
2 stops21h 58mMultiple Airlines
Sun 11/236:23 pmSWF - SJO
2 stops21h 57mMultiple Airlines
Deal found 10/10$409
This Mytrip deal was found by Cheapflights users on 10/10. 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.
Thu 12/251:16 amSJO - SWF
1 stop8h 51mMultiple Airlines
Fri 1/211:57 amSWF - SJO
1 stop13h 24mMultiple Airlines
Deal found 10/10$442
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/251:31 pmSJO - SWF
1 stop20h 36mMultiple Airlines
Fri 1/211:57 amSWF - SJO
1 stop25h 28mMultiple Airlines
Deal found 10/11$451
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/251:31 pmSJO - SWF
1 stop20h 36mMultiple Airlines
Mon 12/2911:37 amSWF - SJO
2 stops20h 33mMultiple Airlines
Deal found 10/11$496
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/181:19 pmSJO - SWF
1 stop27h 47mMultiple Airlines
Mon 12/2911:37 amSWF - SJO
2 stops20h 33mMultiple Airlines
Deal found 10/12$539
This Kiwi.com deal was found by Cheapflights users on 10/11. 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.
Sun 12/281:16 amSJO - SWF
1 stop8h 31mMultiple Airlines
Fri 1/211:57 amSWF - SJO
1 stop25h 17mMultiple Airlines
Deal found 10/11$680
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/181:31 pmSJO - SWF
1 stop27h 35mMultiple Airlines
Mon 12/228:25 pmSWF - SJO
1 stop17h 00mMultiple Airlines
Deal found 10/11$796

Cheapflights Fare Finder

 
Customize your flight search to find flights from Costa Rica to Stewart 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 October 13, 2025.
Use the filters below to find and compare flights from Costa Rica to New Windsor that are best for you.

Fly from

Costa Rica

Fly to

Stewart

Route

Depart

Return

Price

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Sun 1/25

1:16 am-10:19 am

1 stop8h 03m

New Windsor Stewart

Fri 1/30

11:09 am-12:21 am

1 stop14h 12m

$371

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 11/20

11:24 am-10:22 am

2 stops21h 58m

New Windsor Stewart

Sun 11/23

6:23 pm-3:20 pm

2 stops21h 57m

$409

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 12/25

1:16 am-11:07 am

1 stop8h 51m

New Windsor Stewart

Fri 1/2

11:57 am-12:21 am

1 stop13h 24m

$442

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 12/25

1:31 pm-11:07 am

1 stop20h 36m

New Windsor Stewart

Fri 1/2

11:57 am-12:25 pm

1 stop25h 28m

$451

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Sun 1/18

1:16 am-10:19 am

1 stop8h 03m

New Windsor Stewart

Fri 1/23

11:09 am-12:21 am

1 stop14h 12m

$486

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 12/25

1:31 pm-11:07 am

1 stop20h 36m

New Windsor Stewart

Mon 12/29

11:37 am-7:10 am

2 stops20h 33m

$496

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 12/18

1:19 pm-6:06 pm

1 stop27h 47m

New Windsor Stewart

Mon 12/29

11:37 am-7:10 am

2 stops20h 33m

$539

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 1/8

1:16 am-10:19 am

1 stop8h 03m

New Windsor Stewart

Mon 1/19

11:09 am-12:21 am

1 stop14h 12m

$560

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Sun 12/28

1:16 am-10:47 am

1 stop8h 31m

New Windsor Stewart

Fri 1/2

11:57 am-12:14 pm

1 stop25h 17m

$680

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 10/23

12:35 pm-10:41 am

1 stop20h 06m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/11

Showing 1-10 of 27 results
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Best time to book a flight from Costa Rica to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Costa Rica 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 Costa Rica to New Windsor

What is the cheapest month to book a flight from Costa Rica to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Costa Rica to New Windsor (average of $162). Flying from Costa Rica to New Windsor in August is currently the most expensive (average of $233). 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 Costa Rica to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Costa Rica?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Costa Rica.

  • Can I find deals for flights from Costa Rica to Stewart that include hotel bookings?

    Yes. In addition to deals on Costa Rica to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Costa Rica to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Costa Rica to Stewart.

  • Can I find deals for business class flights from Costa Rica to Stewart?

    Yes. Cheapflights offers flight deals from Costa Rica to Stewart 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 Costa Rica to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Costa Rica to New Windsor (average of $162). Flying from Costa Rica to New Windsor in August is currently the most expensive (average of $233). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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See prices for flight routes from nearby airports that may be better suited for you.
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