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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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$332
(Mytrip)

One-way from

$128
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$343
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. 11% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($21 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 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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/13. 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
Tue 12/26:07 pmSJO - SWF
2 stops39h 12mMultiple Airlines
Deal found 10/13$411
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/2711:43 amSWF - SJO
1 stop23h 36mMultiple Airlines
Tue 12/26:07 pmSJO - SWF
2 stops39h 12mMultiple Airlines
Deal found 10/13$478
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/1311:43 amSWF - SJO
2 stops11h 13mMultiple Airlines
Sun 11/161:30 pmSJO - SWF
1 stop20h 41mMultiple Airlines
Deal found 10/13$480
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 12/245:34 pmSWF - SJO
1 stop19h 08mMultiple Airlines
Wed 1/712:39 pmSJO - SWF
1 stop21h 29mMultiple Airlines
Deal found 10/14$711
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.
Mon 12/228:25 pmSWF - SJO
1 stop16h 49mMultiple Airlines
Thu 1/11:31 pmSJO - SWF
1 stop20h 36mMultiple Airlines
Deal found 10/12$1,190
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 12/2911:37 amSWF - SJO
2 stops20h 33mMultiple Airlines
Sat 1/312:39 pmSJO - SWF
1 stop21h 24mMultiple Airlines
Deal found 10/13$1,195
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.
Mon 12/228:25 pmSWF - SJO
1 stop17h 00mMultiple Airlines
Sun 1/41:16 amSJO - SWF
1 stop8h 31mMultiple Airlines
Deal found 10/12$1,264
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.
Tue 12/2311:43 amSWF - SJO
1 stop24h 59mMultiple Airlines
Sat 1/312:39 pmSJO - SWF
1 stop21h 24mMultiple Airlines
Deal found 10/12$1,296
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 12/2511:43 amSWF - SJO
2 stops20h 27mMultiple Airlines
Sat 1/312:39 pmSJO - SWF
1 stop21h 24mMultiple Airlines
Deal found 10/14$1,308
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 12/2611:57 amSWF - SJO
2 stops20h 13mMultiple Airlines
Sat 1/312:39 pmSJO - SWF
1 stop21h 24mMultiple Airlines
Deal found 10/13$1,346
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 12/2111:43 amSWF - SJO
1 stop24h 59mMultiple Airlines
Sat 1/312:39 pmSJO - SWF
1 stop21h 24mMultiple Airlines
Deal found 10/13$1,358

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 October 14, 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-12:21 am

1 stop14h 12m

San José Juan Santamaria Intl

Fri 1/30

7:22 am-6:43 pm

1 stop10h 21m

$332

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 1/9

11:09 am-12:21 am

1 stop14h 12m

San José Juan Santamaria Intl

Sun 1/11

1:16 am-10:19 am

1 stop8h 03m

$410

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Wed 11/26

12:17 pm-12:15 pm

1 stop24h 58m

San José Juan Santamaria Intl

Tue 12/2

6:07 pm-10:19 am

2 stops39h 12m

$411

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 11/27

11:43 am-10:19 am

1 stop23h 36m

San José Juan Santamaria Intl

Tue 12/2

6:07 pm-10:19 am

2 stops39h 12m

$478

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 11/13

11:43 am-9:56 pm

2 stops11h 13m

San José Juan Santamaria Intl

Sun 11/16

1:30 pm-11:11 am

1 stop20h 41m

$480

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/12

11:09 am-12:21 am

1 stop14h 12m

San José Juan Santamaria Intl

Thu 1/15

1:16 am-10:19 am

1 stop8h 03m

$596

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 12/22

8:25 pm-12:14 pm

1 stop16h 49m

San José Juan Santamaria Intl

Thu 1/1

1:31 pm-11:07 am

1 stop20h 36m

$1,190

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 10/27

3:01 pm-11:30 am

1 stop22h 29m

$128

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 10/24

11:31 am-11:30 am

1 stop25h 59m

$131

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 11/3

12:01 pm-11:39 am

2 stops24h 38m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 20 results
1
2

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 $131). 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 $131). 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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Alternative routes for Stewart to Costa Rica

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