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$354+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJO
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$354
(Kiwi.com)
From Key West to Costa Rica
Search Deals

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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 10/410:47 amEYW - SJO
2 stops26h 43mMultiple Airlines
Sun 10/1211:37 amSJO - EYW
1 stop18h 38mMultiple Airlines
Deal found 9/16$354
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 10/1110:47 amEYW - SJO
2 stops26h 43mMultiple Airlines
Sat 10/1811:37 amSJO - EYW
1 stop18h 38mMultiple Airlines
Deal found 9/16$359
This Expedia deal was found by Cheapflights users on 9/16. 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.
Sat 10/111:04 pmEYW - SJO
2 stops25h 56mJetBlue
Sat 10/181:00 pmSJO - EYW
2 stops21h 09mJetBlue
Deal found 9/16$548
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/1111:22 amEYW - SJO
1 stop26h 38mAmerican Airlines
Sat 10/182:40 pmSJO - EYW
1 stop26h 42mAmerican Airlines
Deal found 9/16$586
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/41:59 pmEYW - SJO
1 stop7h 43mAmerican Airlines
Sun 10/121:00 pmSJO - EYW
1 stop19h 52mAmerican Airlines
Deal found 9/16$720

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 September 17, 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

Sat 10/11

10:47 am-11:30 am

2 stops26h 43m

San José Juan Santamaria Intl

Sat 10/18

11:37 am-8:15 am

1 stop18h 38m

$359

Key WestSan José

EYW - SJO

EYWSJO

Key West

Wed 1/21

2:25 pm-12:21 am

1 stop10h 56m

San José Juan Santamaria Intl

Sun 1/25

1:16 am-12:26 pm

2 stops10h 10m

$488

Key WestSan José

EYW - SJO

EYWSJO

Key West

Wed 1/21

6:31 am-2:10 pm

1 stop8h 39m

San José Juan Santamaria Intl

Mon 1/26

6:25 am-1:06 pm

1 stop5h 41m

$512

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sat 10/11

1:04 pm-1:00 pm

2 stops25h 56m

San José Juan Santamaria Intl

Sat 10/18

1:00 pm-12:09 pm

2 stops21h 09m

$548

Key WestSan José

EYW - SJO

EYWSJO

Key West

Tue 3/10

6:31 am-11:00 am

1 stop6h 29m

San José Juan Santamaria Intl

Wed 3/11

2:55 pm-11:59 pm

1 stop7h 04m

$666

Key WestSan José

EYW - SJO

EYWSJO

Key West

Tue 3/3

6:31 am-12:10 pm

1 stop6h 39m

San José Juan Santamaria Intl

Wed 3/4

1:50 pm-11:59 pm

1 stop9h 09m

$698

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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 September 17, 2025.

When flying from Key West to Costa Rica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 17, 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
10,000 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

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

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

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 8h 39m. 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.

  • What is the cheapest month to book a flight from Key West to Costa Rica?

    Currently, September is the cheapest month in which you can book a flight from Key West to Costa Rica (average of $398). Flying from Key West to Costa Rica in March is currently the most expensive (average of $554). 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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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$535Average$643FlexibilityNo cancel feeOn-time71%

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