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$189+ Cheap flights from New Windsor (SWF) to Costa Rica

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 3/22. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Apr 10 — Apr 171
Fri 4/10
Fri 4/17
1 adult, Economy
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Cheap flight deals from Stewart to Costa Rica

Cheapest flights from Stewart to Costa Rica
Explore the most affordable flight options available from Stewart to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:47 am
SWF
-
SJO
1 stop26h 55m
Multiple Airlines
Sat 4/412:19 pm
SJO
-
SWF
1 stop19h 20m
Multiple Airlines
Deal found 3/10$651
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2811:28 am
SWF
-
SJO
1 stop25h 14m
Multiple Airlines
Sat 4/412:19 pm
SJO
-
SWF
1 stop19h 20m
Multiple Airlines
Deal found 3/10$692
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/58:12 pm
SWF
-
SJO
2 stops41h 02m
Multiple Airlines
Sun 4/1211:38 am
SJO
-
SWF
1 stop21h 12m
Multiple Airlines
Deal found 3/10$816
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/58:12 pm
SWF
-
SJO
2 stops41h 02m
Multiple Airlines
Sat 4/1111:38 am
SJO
-
SWF
1 stop21h 30m
Multiple Airlines
Deal found 3/10$821
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/310:00 am
SWF
-
SJO
1 stop26h 42m
Multiple Airlines
Sun 4/1211:38 am
SJO
-
SWF
2 stops21h 53m
Multiple Airlines
Deal found 3/10$856
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/411:45 am
SWF
-
SJO
1 stop24h 57m
Multiple Airlines
Sun 4/1211:38 am
SJO
-
SWF
2 stops21h 53m
Multiple Airlines
Deal found 3/10$911
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/310:00 am
SWF
-
SJO
1 stop26h 42m
Multiple Airlines
Sat 4/1111:38 am
SJO
-
SWF
1 stop21h 30m
Multiple Airlines
Deal found 3/10$948

Find flight deals from Stewart to Costa Rica

Keep the following information in mind while searching for Stewart to Costa Rica flight deals. Data was last updated March 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$651
(Kiwi.com)

One-way from

$189
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$439
Provider with most accurate pricing for New York (NYC)-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-San José Juan Santamaria Intl flights.
Search Deals
From New Windsor Stewart to Costa Rica
Search Deals
One-way flight from New Windsor Stewart to Costa Rica
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in March 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Costa Rica 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 March 11, 2026.
Use the filters below to find and compare flights from New Windsor to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sat 3/28

11:28 am-10:42 am

1 stop25h 14m

San José Juan Santamaria Intl

Sat 4/4

12:19 pm-9:39 am

1 stop19h 20m

$692

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 4/5

8:12 pm-11:14 am

2 stops41h 02m

San José Juan Santamaria Intl

Sat 4/11

11:38 am-11:08 am

1 stop21h 30m

$821

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 4/3

10:00 am-10:42 am

1 stop26h 42m

San José Juan Santamaria Intl

Sun 4/12

11:38 am-10:50 am

1 stop21h 12m

$940

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 4/5

11:48 am-10:42 am

1 stop24h 54m

San José Juan Santamaria Intl

Sun 4/12

11:38 am-10:50 am

1 stop21h 12m

$983

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sat 4/4

11:45 am-10:42 am

1 stop24h 57m

San José Juan Santamaria Intl

Sat 4/11

11:38 am-11:08 am

1 stop21h 30m

$1,003
Cheapest one-way

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 3/22

10:29 am-11:14 am

1 stop26h 45m

$189

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 4/12

11:45 am-11:14 am

1 stop25h 29m

$203

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 4/19

11:45 am-11:33 am

1 stop25h 48m

$214
Quickest one-way

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 3/23

12:11 pm-10:42 am

2 stops24h 31m

$220

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 4/16

11:45 am-11:33 am

1 stop25h 48m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 13 resultsSorted by cheapest first
1
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Best time to book a flight from Stewart to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica 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 Costa Rica

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

Currently, November is the cheapest month in which you can book a flight from New Windsor to Costa Rica (average of $122). Flying from New Windsor to Costa Rica 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 Costa Rica. 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 from for flights from New Windsor to Costa Rica?

    Most people fly from New Windsor Stewart (SWF) if they book a flight from New Windsor to Costa Rica. New Windsor Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from New Windsor to Costa Rica (average of $122). Flying from New Windsor to Costa Rica 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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