$501 Find Cheap Flights from Key West to Costa Rica

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Costa Rica departing on 6/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Book Cheap Key West to Costa Rica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Costa Rica that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Costa Rica

Sun, Jun 14 - Fri, Jun 19
Multiple Airlines Logo
9:16 pm - 3:11 pm
EYW
-
SJO
19h 55m
1 stop
Multiple Airlines Logo
1:21 pm - 1:58 pm
SJO
-
EYW
22h 37m
2 stops
$501Multiple Airlines
Sun, Jun 14 - Fri, Jun 19
Multiple Airlines Logo
9:16 pm - 3:11 pm
EYW
-
SJO
19h 55m
1 stop
Multiple Airlines Logo
4:35 pm - 10:06 am
SJO
-
EYW
39h 31m
3 stops
$588Multiple Airlines
Mon, Jul 20 - Mon, Jul 27
American Airlines Logo
4:40 pm - 1:12 pm
EYW
-
SJO
22h 32m
2 stops
American Airlines Logo
3:19 pm - 4:08 pm
SJO
-
EYW
22h 49m
2 stops
$638American Airlines
Mon, Jul 20 - Mon, Jul 27
American Airlines Logo
7:40 pm - 11:56 am
EYW
-
SJO
18h 16m
1 stop
American Airlines Logo
6:00 am - 7:06 pm
SJO
-
EYW
11h 06m
1 stop
$694American Airlines
Sun, Jun 14 - Fri, Jun 19
American Airlines Logo
1:39 pm - 7:24 pm
EYW
-
SJO
7h 45m
1 stop
American Airlines Logo
6:00 am - 7:10 pm
SJO
-
EYW
11h 10m
1 stop
$739American Airlines
Thu, May 7 - Sun, May 10
United Airlines Logo
4:47 pm - 12:21 pm
EYW
-
SJO
21h 34m
1 stop
United Airlines Logo
7:55 am - 4:02 pm
SJO
-
EYW
30h 07m
1 stop
$1,068United Airlines
Thu, May 7 - Sun, May 10
United Airlines Logo
4:47 pm - 12:21 pm
EYW
-
SJO
21h 34m
1 stop
United Airlines Logo
1:25 pm - 4:02 pm
SJO
-
EYW
24h 37m
1 stop
$1,145United Airlines
Booking Insights

KAYAK's insights & trends for Key West to Costa Rica flights

Get data-powered insights and trends into flights from Key West to Costa Rica to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Key West to Costa Rica?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Key West to Costa Rica were found on American Airlines ($638) and United Airlines ($1,068).

Good to know

Cheapest flight$501
Flight from Key West to San José

FAQs - booking Costa Rica flights

  • How does KAYAK find such low prices on flights from Key West to Costa Rica?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Costa Rica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Costa Rica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Costa Rica is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Costa Rica?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Key West to Costa Rica with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Costa Rica?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Key West to Costa Rica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Key West to Costa Rica

 
Need help choosing which airline to fly with from Key West to Costa Rica? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11659 reviews
7.2Comfort
6.9Entertainment
7.5Boarding
7.9Crew
6.4Food
Airline reviews

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

4.0 OkayAnonymous, Apr 2026
MIA - UIO
Read more American Airlines reviews

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

Everything you need to know for your flight from Key West to Costa Rica

Information on your arrival and departure airports