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$137+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$342
(Mytrip)

One-way from

$137
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$377
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.
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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. 8% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Wed 11/2612:17 pmSWF - SJO
1 stop24h 58mMultiple Airlines
Wed 12/311:24 amSJO - SWF
1 stop22h 39mMultiple Airlines
Deal found 11/25$531
This Mytrip deal was found by Cheapflights users on 11/25. 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 12/157:30 pmSWF - SJO
1 stop17h 12mMultiple Airlines
Mon 12/227:22 amSJO - SWF
1 stop9h 58mMultiple Airlines
Deal found 11/25$622
This Mytrip deal was found by Cheapflights users on 11/25. 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
1 stop17h 00mMultiple Airlines
Sun 12/2812:39 pmSJO - SWF
2 stops21h 08mMultiple Airlines
Deal found 11/25$630
This Mytrip deal was found by Cheapflights users on 11/24. 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 12/157:30 pmSWF - SJO
1 stop17h 12mMultiple Airlines
Fri 1/97:22 amSJO - SWF
1 stop10h 21mMultiple Airlines
Deal found 11/24$642
This Mytrip deal was found by Cheapflights users on 11/24. 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.
Fri 12/196:56 pmSWF - SJO
3 stops41h 46mMultiple Airlines
Sun 12/287:22 amSJO - SWF
2 stops26h 25mMultiple Airlines
Deal found 11/24$762
This Mytrip deal was found by Cheapflights users on 11/25. 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.
Sat 12/209:45 amSWF - SJO
3 stops27h 40mMultiple Airlines
Sun 12/2812:39 pmSJO - SWF
2 stops21h 08mMultiple Airlines
Deal found 11/25$775

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 November 26, 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 1/9

11:09 am-11:37 am

2 stops25h 28m

San José Juan Santamaria Intl

Sun 1/18

12:33 pm-10:19 am

2 stops20h 46m

$460

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/12

7:33 pm-11:37 am

1 stop17h 04m

San José Juan Santamaria Intl

Mon 1/19

7:22 am-6:43 pm

1 stop10h 21m

$533

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/15

7:30 pm-11:42 am

1 stop17h 12m

San José Juan Santamaria Intl

Mon 12/22

7:22 am-6:20 pm

1 stop9h 58m

$622

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

Sun 12/28

12:39 pm-10:47 am

2 stops21h 08m

$630

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/15

7:30 pm-11:42 am

1 stop17h 12m

San José Juan Santamaria Intl

Fri 1/9

7:22 am-6:43 pm

1 stop10h 21m

$642

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 12/19

6:56 pm-11:42 am

3 stops41h 46m

San José Juan Santamaria Intl

Sun 12/28

7:22 am-10:47 am

2 stops26h 25m

$762

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sat 12/20

9:45 am-12:25 pm

3 stops27h 40m

San José Juan Santamaria Intl

Sun 12/28

12:39 pm-10:47 am

2 stops21h 08m

$775

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 12/19

6:56 pm-11:42 am

2 stops17h 46m

San José Juan Santamaria Intl

Thu 12/25

12:39 pm-11:07 am

2 stops21h 28m

$902

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 2/9

11:09 am-12:22 pm

1 stop26h 13m

$137

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 12/12

7:30 pm-11:42 am

1 stop17h 12m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 23 results
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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 $127). 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 $127). 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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