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$128+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap 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 August 17, 2025.

Round-trip from

$389
(Kiwi.com)

One-way from

$128
(Booking.com)

Popular in

December

Cheapest in

October

Average price

$466
From New Windsor Stewart to Costa Rica
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One-way flight from New Windsor Stewart to Costa Rica
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Highest demand for flights based on searches. 11% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/16. 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 12/512:27 pmSWF - SJO
1 stop12h 54mMultiple Airlines
Sun 12/71:16 amSJO - SWF
1 stop9h 21mMultiple Airlines
Deal found 8/16$389
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 8/291:55 pmSWF - SJO
1 stop23h 17mMultiple Airlines
Sun 8/3112:18 pmSJO - SWF
1 stop22h 47mMultiple Airlines
Deal found 8/16$425
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:36 pmSWF - SJO
1 stop19h 36mMultiple Airlines
Sun 8/3112:18 pmSJO - SWF
1 stop22h 47mMultiple Airlines
Deal found 8/15$468
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/187:37 pmSWF - SJO
1 stop17h 35mMultiple Airlines
Sun 8/2412:18 pmSJO - SWF
1 stop26h 28mMultiple Airlines
Deal found 8/15$484
This Mytrip deal was found by Cheapflights users on 8/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:50 pmSWF - SJO
2 stops22h 23mMultiple Airlines
Sun 8/242:37 pmSJO - SWF
2 stops24h 09mMultiple Airlines
Deal found 8/16$587

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 August 17, 2025.
Use the filters below to find and compare flights from New Windsor to Costa Rica that are best for you.

Fly from

Stewart

Fly to

Costa Rica

Route

Depart

Return

Price

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 12/5

12:27 pm-12:21 am

1 stop12h 54m

San José Juan Santamaria Intl

Sun 12/7

1:16 am-11:37 am

1 stop9h 21m

$389

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 8/29

1:55 pm-11:12 am

1 stop23h 17m

San José Juan Santamaria Intl

Sun 8/31

12:18 pm-1:05 pm

1 stop22h 47m

$425

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 1/2

11:57 am-9:52 pm

2 stops10h 55m

San José Juan Santamaria Intl

Thu 1/8

1:16 am-10:19 am

1 stop8h 03m

$898

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 8/22

5:36 pm-11:12 am

1 stop19h 36m

$128

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 8/29

1:55 pm-11:12 am

1 stop23h 17m

$133

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 8/25

5:36 pm-11:12 am

1 stop19h 36m

$134

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 10/24

11:31 am-11:30 am

1 stop25h 59m

$142

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 10/31

11:31 am-10:41 am

2 stops25h 10m

$147

New WindsorLiberia

SWF - LIR

SWFLIR

New Windsor Stewart

Fri 8/22

5:36 pm-3:40 pm

2 stops24h 04m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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, September is the cheapest month in which you can book a flight from New Windsor to Costa Rica (average of $398). Flying from New Windsor to Costa Rica in March is currently the most expensive (average of $555). 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, September is the cheapest month in which you can book a flight from New Windsor to Costa Rica (average of $398). Flying from New Windsor to Costa Rica in March is currently the most expensive (average of $555). 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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