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$593+ Cheap flights from Key West (EYW) 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJO
Feb 22 — Mar 11
Sun 2/22
Sun 3/1
1 adult, Economy
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Cheap flight deals from Key West to Costa Rica

Cheapest flights from Key West to Costa Rica
Explore the most affordable flight options available from Key West to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 23, 2026.

This American Airlines deal was found by Cheapflights users on 1/21. 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.
Sat 8/294:51 pm
EYW
-
SJO
2 stops20h 59m
American Airlines
Thu 9/107:00 am
SJO
-
EYW
2 stops26h 21m
American Airlines
Deal found 1/21$593
This American Airlines deal was found by Cheapflights users on 1/22. 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.
Mon 8/31:34 pm
EYW
-
SJO
1 stop7h 40m
American Airlines
Sat 8/86:00 am
SJO
-
EYW
1 stop10h 39m
American Airlines
Deal found 1/22$608
This American Airlines deal was found by Cheapflights users on 1/21. 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 1/217:45 pm
EYW
-
SJO
1 stop26h 17m
American Airlines
Mon 1/266:00 am
SJO
-
EYW
1 stop6h 03m
American Airlines
Deal found 1/21$672
This American Airlines deal was found by Cheapflights users on 1/22. 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.
Sat 3/147:42 pm
EYW
-
SJO
1 stop25h 51m
American Airlines
Wed 3/187:00 am
SJO
-
EYW
1 stop7h 49m
American Airlines
Deal found 1/22$686
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/86:43 pm
EYW
-
SJO
2 stops20h 11m
American Airlines
Sat 2/148:00 am
SJO
-
EYW
1 stop9h 54m
American Airlines
Deal found 1/21$825

Find flight deals from Key West to Costa Rica

Keep the following information in mind while searching for Key West to Costa Rica flight deals. Data was last updated January 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$551
(American Airlines)
Provider with most accurate pricing for Key West-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-San José Juan Santamaria Intl flights.
Search Deals
From Key West to Costa Rica
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West 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 23, 2026.
Use the filters below to find and compare flights from Key West to Costa Rica that are best for you.

Fly from

Key West

Fly to

Costa Rica

Route

Depart

Return

Price

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sat 3/14

7:42 pm-7:33 pm

1 stop25h 51m

San José Juan Santamaria Intl

Wed 3/18

7:00 am-4:49 pm

1 stop7h 49m

$686

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sun 2/8

6:43 pm-1:54 pm

2 stops20h 11m

San José Juan Santamaria Intl

Sat 2/14

8:00 am-6:54 pm

1 stop9h 54m

$825

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sat 3/14

12:50 pm-10:36 pm

2 stops35h 46m

San José Juan Santamaria Intl

Wed 3/18

4:15 pm-11:59 am

3 stops41h 44m

$1,562

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Best time to book a flight from Key West to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Key West 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 Key West 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 January 23, 2026.
See what other customers who have flown with American Airlines from Key West to Costa Rica have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,177 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,177 reviews
American Airlines
7.2
Good
11,177 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

Related info for your journey

Find useful and relevant information for your journey from Key West 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 Key West to Costa Rica?

    Key West (EYW), located 2.6 mi from the city center, is the airport you fly out of when you book flights from Key West to Costa Rica.

  • How long is the flight from Key West to Costa Rica?

    American Airlines can get you from Key West to Costa Rica in just under 25h 51m. Your travel time can differ by up to . There are 1018 mi between Key West and Costa Rica.

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

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

  • How can I find direct flights from Key West to Costa Rica?

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

  • Can I find deals for business class flights from Key West to Costa Rica?

    Yes. Cheapflights offers flight deals from Key West 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.

See more FAQs

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Alternative routes for Key West to Costa Rica

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Top airline flying from Key West to Costa Rica

Discover the top airline that operate flights from Key West 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 January 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$523Average$643FlexibilityNo cancel feeOn-time71%

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