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San José

$470+ Cheap flights from Key West (EYW) to San José (SJO)

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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJO
May 29 — Jun 51
Fri 5/29
Fri 6/5
1 adult, Economy
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Cheap flight deals from Key West to San José

Cheapest flights from Key West to San José
Explore the most affordable flight options available from Key West to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Thu 5/2812:05 pm
EYW
-
SJO
1 stop29h 13m
Multiple Airlines
Thu 6/49:35 am
SJO
-
EYW
1 stop23h 52m
Multiple Airlines
Deal found 4/28$470
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 4/309:46 am
EYW
-
SJO
1 stop7h 32m
Multiple Airlines
Sun 5/37:00 am
SJO
-
EYW
1 stop27h 26m
Multiple Airlines
Deal found 4/29$558
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 4/2911:51 am
EYW
-
SJO
1 stop29h 27m
Multiple Airlines
Tue 5/56:19 pm
SJO
-
EYW
2 stops38h 05m
Multiple Airlines
Deal found 4/28$644
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/281:01 pm
EYW
-
SJO
2 stops24h 49m
American Airlines
Thu 6/43:08 pm
SJO
-
EYW
2 stops19h 08m
American Airlines
Deal found 4/28$659
This American Airlines deal was found by Cheapflights users on 4/28. 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 4/296:45 am
EYW
-
SJO
1 stop14h 22m
American Airlines
Tue 5/52:22 pm
SJO
-
EYW
1 stop6h 36m
American Airlines
Deal found 4/28$676
This American Airlines deal was found by Cheapflights users on 4/29. 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 4/308:05 am
EYW
-
SJO
2 stops13h 02m
American Airlines
Sun 5/32:22 pm
SJO
-
EYW
2 stops20h 59m
American Airlines
Deal found 4/29$762
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/144:47 pm
EYW
-
SJO
1 stop28h 50m
United Airlines
Sun 5/177:55 am
SJO
-
EYW
1 stop30h 07m
United Airlines
Deal found 4/26$1,068

Find flight deals from Key West to San José

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 29, 2026.

Round-trip from

$470
(Kiwi.com)
From Key West to San José Juan Santamaria Intl
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to San José 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 April 29, 2026.
Use the filters below to find and compare flights from Key West to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestSan José

EYW - SJO

EYWSJO

Key West

Thu 5/28

12:05 pm-3:18 pm

1 stop29h 13m

San José Juan Santamaria Intl

Thu 6/4

9:35 am-11:27 am

1 stop23h 52m

$470
Quickest round-trip

Key WestSan José

EYW - SJO

EYWSJO

Key West

Thu 5/28

1:01 pm-11:50 am

2 stops24h 49m

San José Juan Santamaria Intl

Thu 6/4

3:08 pm-12:16 pm

2 stops19h 08m

$659

Key WestSan José

EYW - SJO

EYWSJO

Key West

Thu 5/14

4:47 pm-7:37 pm

1 stop28h 50m

San José Juan Santamaria Intl

Sun 5/17

7:55 am-4:02 pm

1 stop30h 07m

$1,068

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Sorted by cheapest first

Best time to book a flight from Key West to San José

Have a flexible travel schedule? Discover the best time to fly to San José 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.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated April 29, 2026.
Read reviews from past customers who have flown American Airlines from Key West to San José. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,678 reviews

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

7.9

Food

6.4

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,678 reviews
American Airlines
7.1
Good
11,678 reviews

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Crew

7.9

Food

6.4

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

Related info for your journey

Find useful and relevant information for your journey from Key West to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Key West to San José?

    For as low as $659, American Airlines can have you in San José from Key West in 24h 49m. The distance between Key West and San José is about 1018 mi. This flight may include one or multiple stops.

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

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

  • How can I find direct flights from Key West to San José?

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

  • Can I find deals for business class flights from Key West to San José?

    Yes. Cheapflights offers flight deals from Key West to San José 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

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Alajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio

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Top airline flying from Key West to San José

Discover the top airline that operate flights from Key West to San José. 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 April 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$523Average$747FlexibilityNo cancel feeOn-time71%

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