HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Costa Rica

$170+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJO
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Costa Rica with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

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.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-San José Juan Santamaria Intl flights.
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Stewart to Costa Rica

One-way flights from Stewart to Costa Rica
Search for one-way flight options from Stewart to Costa Rica. Find affordable one-way fares based on user searches. Data last updated January 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 2/811:48 am
SWF
-
SJO
1 stop24h 49m
Multiple Airlines
Deal found 1/14$170
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 2/67:33 pm
SWF
-
SJO
1 stop17h 04m
Multiple Airlines
Deal found 1/13$175
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 3/810:09 am
SWF
-
SJO
1 stop27h 13m
Multiple Airlines
Deal found 1/13$176
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Mon 2/27:33 pm
SWF
-
SJO
1 stop17h 04m
Multiple Airlines
Deal found 1/14$202
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 3/510:09 am
SWF
-
SJO
2 stops26h 31m
Multiple Airlines
Deal found 1/13$203
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Mon 3/2312:11 pm
SWF
-
SJO
2 stops24h 31m
Multiple Airlines
Deal found 1/14$205
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 1/197:33 pm
SWF
-
SJO
1 stop17h 04m
Multiple Airlines
Deal found 1/13$223
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 1/2512:13 pm
SWF
-
SJO
2 stops31h 42m
Multiple Airlines
Deal found 1/14$224
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 2/185:46 pm
SWF
-
LIR
3 stops46h 29m
Multiple Airlines
Deal found 1/13$268
This Kiwi.com deal was found by Cheapflights users on 1/13. 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.
Tue 2/1712:41 pm
SWF
-
LIR
3 stops51h 39m
Multiple Airlines
Deal found 1/13$410
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Sun 2/157:28 pm
SWF
-
LIR
3 stops17h 22m
Multiple Airlines
Deal found 1/14$575
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 2/1211:42 am
SWF
-
LIR
3 stops25h 48m
Multiple Airlines
Deal found 1/14$668

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 January 15, 2026.
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

Sun 2/8

11:48 am-11:37 am

1 stop24h 49m

$170

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Fri 2/6

7:33 pm-11:37 am

1 stop17h 04m

$175

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 2/2

7:33 pm-11:37 am

1 stop17h 04m

$202

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Thu 3/5

10:09 am-11:40 am

2 stops26h 31m

$203

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 3/23

12:11 pm-10:42 am

2 stops24h 31m

$205

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Sun 3/8

10:09 am-10:40 am

2 stops26h 31m

$212

New WindsorSan José

SWF - SJO

SWFSJO

New Windsor Stewart

Mon 1/19

7:33 pm-11:37 am

1 stop17h 04m

$223

New WindsorLiberia

SWF - LIR

SWFLIR

New Windsor Stewart

Wed 2/18

5:46 pm-3:15 pm

3 stops46h 29m

$268

New WindsorLiberia

SWF - LIR

SWFLIR

New Windsor Stewart

Tue 2/17

12:41 pm-3:20 pm

3 stops51h 39m

$410

New WindsorLiberia

SWF - LIR

SWFLIR

New Windsor Stewart

Sun 2/15

7:28 pm-11:50 am

3 stops17h 22m

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 11 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 $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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to San José flights
John F Kennedy Intl to Panama City flights
Newark to San José flights
Newark to Panama City flights
John F Kennedy Intl to Guatemala City flights
John F Kennedy Intl to Liberia flights
Newark to Liberia flights
John F Kennedy Intl to San Salvador flights
LaGuardia to San José flights
LaGuardia to Panama City flights
Newark to Guatemala City flights
LaGuardia to Liberia flights
LaGuardia to Guatemala City flights
LaGuardia to San Salvador flights
John F Kennedy Intl to San Pedro Sula flights
LaGuardia to Philip S.W.Goldson flights
Newark to Philip S.W.Goldson flights
Newark to San Salvador flights
John F Kennedy Intl to Philip S.W.Goldson flights
Newark to San Pedro Sula flights
LaGuardia to San Pedro Sula flights
John F Kennedy Intl to Coxen Hole flights
LaGuardia to Coxen Hole flights
John F Kennedy Intl to Managua flights
Newark to Coxen Hole flights
Newark to Managua flights
LaGuardia to Managua flights
Syracuse to San José flights
Buffalo to San José flights
John F Kennedy Intl to David flights
Newark to David flights
Rochester to San José flights
Rochester to Liberia flights
Rochester to Panama City flights
Buffalo to Liberia flights
Albany to Liberia flights
Syracuse to Liberia flights
Albany to San José flights
White Plains to San José flights
Buffalo to Philip S.W.Goldson flights
Buffalo to Panama City flights
Rochester to Philip S.W.Goldson flights
Syracuse to Guatemala City flights
White Plains to Panama City flights
Albany to Panama City flights
Buffalo to Guatemala City flights
Albany to San Salvador flights
White Plains to Philip S.W.Goldson flights
White Plains to Liberia flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.