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Costa Rica

$242+ Cheap flights from Westchester County to Costa Rica

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJO
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Westchester County to Costa Rica

Keep the following information in mind while searching for Westchester County to Costa Rica flight deals. Data was last updated August 14, 2025.

Round-trip from

$242
(American Airlines)

One-way from

$194
(Delta)

Popular in

December

Cheapest in

October

Average price

$466
From Westchester County to Costa Rica
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One-way flight from Westchester County 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 Westchester County to Costa Rica

Cheapest flights from Westchester County to Costa Rica
Explore the most affordable flight options available from Westchester County to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:55 pmHPN - SJO
2 stops20h 43mAmerican Airlines
Tue 10/211:00 pmSJO - HPN
2 stops20h 29mAmerican Airlines
Deal found 8/14$242
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/97:42 amHPN - SJO
2 stops14h 00mAmerican Airlines
Fri 9/126:00 amSJO - HPN
2 stops26h 45mAmerican Airlines
Deal found 8/13$312
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:30 amHPN - SJO
2 stops15h 12mAmerican Airlines
Sun 9/146:00 amSJO - HPN
2 stops26h 45mAmerican Airlines
Deal found 8/13$317
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:50 pmHPN - SJO
1 stop19h 55mAmerican Airlines
Tue 9/166:00 amSJO - HPN
2 stops15h 26mAmerican Airlines
Deal found 8/13$319
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:42 pmHPN - SJO
2 stops19h 23mAmerican Airlines
Sat 12/63:20 pmSJO - HPN
2 stops20h 42mAmerican Airlines
Deal found 8/13$322
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/147:59 amHPN - SJO
2 stops36h 12mAmerican Airlines
Wed 9/1712:12 pmSJO - HPN
2 stops21h 17mAmerican Airlines
Deal found 8/13$325
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:42 pmHPN - SJO
2 stops17h 23mAmerican Airlines
Sun 12/73:20 pmSJO - HPN
2 stops20h 42mAmerican Airlines
Deal found 8/13$327
This Expedia deal was found by Cheapflights users on 8/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:59 pmHPN - SJO
1 stop17h 43mJetBlue
Tue 10/2112:45 pmSJO - HPN
1 stop8h 15mJetBlue
Deal found 8/14$330
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amHPN - SJO
1 stop15h 02mAmerican Airlines
Tue 12/93:50 pmSJO - HPN
1 stop16h 28mAmerican Airlines
Deal found 8/12$331
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:00 amHPN - SJO
1 stop15h 02mAmerican Airlines
Sun 12/73:50 pmSJO - HPN
2 stops21h 56mAmerican Airlines
Deal found 8/12$340
This JetBlue deal was found by Cheapflights users on 8/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:00 amHPN - SJO
1 stop7h 06mJetBlue
Mon 11/32:01 pmSJO - HPN
1 stop8h 01mJetBlue
Deal found 8/13$341
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/175:29 pmHPN - SJO
2 stops20h 26mAmerican Airlines
Wed 8/202:40 pmSJO - HPN
2 stops20h 25mAmerican Airlines
Deal found 8/12$370

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County 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 14, 2025.
Use the filters below to find and compare flights from Westchester County to Costa Rica that are best for you.

Fly from

Westchester County

Fly to

Costa Rica

Route

Depart

Return

Price

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Tue 10/7

6:55 pm-1:38 pm

2 stops20h 43m

San José Juan Santamaria Intl

Tue 10/21

1:00 pm-11:29 am

2 stops20h 29m

$242

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Mon 9/15

4:30 pm-11:12 am

2 stops20h 42m

San José Juan Santamaria Intl

Wed 9/17

12:12 pm-1:05 pm

2 stops22h 53m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Mon 9/15

4:30 pm-11:12 am

2 stops20h 42m

San José Juan Santamaria Intl

Thu 9/18

12:12 pm-10:45 am

2 stops20h 33m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Wed 9/10

10:00 am-7:42 pm

2 stops11h 42m

San José Juan Santamaria Intl

Mon 9/15

6:00 am-11:29 am

2 stops27h 29m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Thu 9/11

4:30 pm-6:11 pm

2 stops27h 41m

San José Juan Santamaria Intl

Tue 9/16

6:00 am-11:26 pm

2 stops15h 26m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Sat 9/13

4:30 pm-7:42 pm

2 stops29h 12m

San José Juan Santamaria Intl

Tue 9/16

6:00 am-11:26 pm

2 stops15h 26m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Fri 9/12

5:29 pm-12:45 pm

2 stops21h 16m

San José Juan Santamaria Intl

Thu 9/18

12:12 pm-10:45 am

2 stops20h 33m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Sat 9/13

4:30 pm-11:12 am

2 stops20h 42m

San José Juan Santamaria Intl

Wed 9/17

12:12 pm-11:29 am

2 stops21h 17m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Thu 9/11

6:59 pm-6:11 pm

2 stops25h 12m

San José Juan Santamaria Intl

Thu 9/18

12:12 pm-9:22 am

2 stops19h 10m

$312

White PlainsSan José

HPN - SJO

HPNSJO

White Plains Westchester County

Wed 9/10

10:00 am-7:42 pm

2 stops11h 42m

San José Juan Santamaria Intl

Fri 9/12

6:00 am-1:11 pm

2 stops29h 11m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 34 results
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Best time to book a flight from Westchester County to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Westchester County 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 Westchester County to Costa Rica
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Costa Rica. Reviews last updated August 14, 2025.
See what other customers who have flown with American Airlines from Westchester County to Costa Rica have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Westchester County 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 Westchester County to Costa Rica?

    Currently, September is the cheapest month in which you can book a flight from Westchester County to Costa Rica (average of $398). Flying from Westchester County 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Westchester County to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Westchester County to Costa Rica

Discover the top airline that operate flights from Westchester County to Costa Rica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$343Average$675FlexibilityNo cancel feeOn-time71%

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