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$375+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJO
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Cheap 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$375
(Kiwi.com)
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.
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From Key West to Costa Rica
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Find 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 October 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:19 amEYW - SJO
2 stops26h 06mMultiple Airlines
Fri 12/121:31 pmSJO - EYW
1 stop22h 59mMultiple Airlines
Deal found 10/21$375
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:55 amEYW - SJO
1 stop26h 24mMultiple Airlines
Mon 12/11:20 pmSJO - EYW
2 stops20h 45mMultiple Airlines
Deal found 10/22$473
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/27:00 amEYW - SJO
1 stop6h 11mAmerican Airlines
Tue 12/97:00 amSJO - EYW
1 stop11h 35mAmerican Airlines
Deal found 10/20$494
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 12/56:33 pmEYW - SJO
2 stops20h 23mAmerican Airlines
Fri 12/127:00 amSJO - EYW
2 stops14h 18mAmerican Airlines
Deal found 10/21$516
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Tue 12/27:00 amEYW - SJO
1 stop15h 05mAmerican Airlines
Sun 12/77:00 amSJO - EYW
1 stop8h 57mAmerican Airlines
Deal found 10/21$517
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/242:30 pmEYW - SJO
1 stop22h 55mSpirit Airlines
Tue 12/301:31 pmSJO - EYW
1 stop22h 59mSpirit Airlines
Deal found 10/23$557

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 October 23, 2025.
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

Fri 12/5

8:55 am-11:42 am

1 stop27h 47m

San José Juan Santamaria Intl

Fri 12/12

1:31 pm-1:30 pm

1 stop22h 59m

$377

Key WestSan José

EYW - SJO

EYWSJO

Key West

Fri 11/28

8:55 am-10:19 am

1 stop26h 24m

San José Juan Santamaria Intl

Mon 12/1

1:20 pm-11:05 am

2 stops20h 45m

$473

Key WestSan José

EYW - SJO

EYWSJO

Key West

Tue 12/2

7:00 am-12:11 pm

1 stop6h 11m

San José Juan Santamaria Intl

Tue 12/9

7:00 am-7:35 pm

1 stop11h 35m

$494

Key WestSan José

EYW - SJO

EYWSJO

Key West

Fri 12/5

6:33 pm-1:56 pm

2 stops20h 23m

San José Juan Santamaria Intl

Fri 12/12

7:00 am-10:18 pm

2 stops14h 18m

$516

Key WestSan José

EYW - SJO

EYWSJO

Key West

Tue 12/2

7:00 am-12:11 pm

1 stop6h 11m

San José Juan Santamaria Intl

Sun 12/7

7:00 am-11:07 pm

1 stop15h 07m

$517

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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

What is the cheapest time of day to fly from EYW to CR?

Find hourly flight availability from Key West to Costa Rica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2025.

It’s optimal to fly from Key West to Costa Rica in the evening. By choosing this option you can save up to 57% on the cost of your flight, compared to a flight in the morning.

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 October 23, 2025.
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
11,033 reviews

Food

6.4

Comfort

7.2

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

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
11,033 reviews
American Airlines
7.2
Good
11,033 reviews

Food

6.4

Comfort

7.2

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

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 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 6h 11m. 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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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$535Average$643FlexibilityNo cancel feeOn-time71%

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