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Stewart

$158+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — SWF
Feb 18 — Feb 251
Wed 2/18
Wed 2/25
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 January 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Popular in

April

Cheapest in

October

Average price

$317
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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Highest demand for flights based on searches. 5% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 19, 2026.

This eDestinos deal was found by Cheapflights users on 1/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:19 am
SJO
-
SWF
1 stop24h 36m
Multiple Airlines
Sun 5/311:45 am
SWF
-
SJO
1 stop29h 32m
Multiple Airlines
Deal found 1/19$440

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 January 19, 2026.
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

Sat 4/25

8:19 am-10:55 am

1 stop24h 36m

New Windsor Stewart

Sun 5/3

11:45 am-3:17 pm

1 stop29h 32m

$440

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 2/5

1:30 pm-10:19 am

1 stop19h 49m

$158

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Sun 2/1

1:30 pm-10:19 am

1 stop19h 49m

$180

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 1/29

12:33 pm-6:43 pm

1 stop29h 10m

$193

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Wed 3/25

12:24 pm-9:39 am

1 stop19h 15m

$205

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Wed 4/8

12:24 pm-10:55 am

1 stop20h 31m

$209

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Tue 2/3

12:33 pm-9:58 am

3 stops44h 25m

$241

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 3/26

11:38 am-11:31 am

2 stops21h 53m

$243

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Thu 3/12

11:38 am-9:02 am

1 stop19h 24m

$248

San JoséNew Windsor

SJO - SWF

SJOSWF

San José Juan Santamaria Intl

Tue 1/27

8:05 pm-11:33 am

2 stops38h 28m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 18 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 $231). 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 $231). 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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Alternative routes for Costa Rica to Stewart

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