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$368+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJO
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/2712:15 pmEYW - SJO
1 stop25h 00mMultiple Airlines
Mon 12/11:20 pmSJO - EYW
2 stops20h 45mMultiple Airlines
Deal found 10/29$368
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/148:55 amEYW - SJO
1 stop27h 44mMultiple Airlines
Mon 11/171:30 pmSJO - EYW
2 stops20h 35mMultiple Airlines
Deal found 10/29$379
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/218:55 amEYW - SJO
1 stop26h 24mMultiple Airlines
Mon 11/241:20 pmSJO - EYW
2 stops19h 59mMultiple Airlines
Deal found 10/29$402
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 12/27:00 amEYW - SJO
1 stop15h 05mAmerican Airlines
Tue 12/91:15 pmSJO - EYW
1 stop8h 52mAmerican Airlines
Deal found 10/28$494
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/24:18 pmEYW - SJO
1 stop5h 47mAmerican Airlines
Sun 12/77:00 amSJO - EYW
1 stop11h 35mAmerican Airlines
Deal found 10/30$517
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/142:58 pmEYW - SJO
1 stop8h 09mDelta
Mon 11/177:00 amSJO - EYW
1 stop9h 23mDelta
Deal found 10/29$530
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 11/146:33 pmEYW - SJO
2 stops18h 39mAmerican Airlines
Mon 11/173:11 pmSJO - EYW
2 stops20h 32mAmerican Airlines
Deal found 10/29$607

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$368
(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.
Search Deals
From Key West to San José Juan Santamaria Intl
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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 October 30, 2025.
Use the filters below to find and compare flights from Key West to San José that are best for you.

Fly from

Key West

Fly to

San José

Route

Depart

Return

Price

Key WestSan José

EYW - SJO

EYWSJO

Key West

Thu 11/27

12:15 pm-12:15 pm

1 stop25h 00m

San José Juan Santamaria Intl

Mon 12/1

1:20 pm-11:05 am

2 stops20h 45m

$368

Key WestSan José

EYW - SJO

EYWSJO

Key West

Fri 11/14

8:55 am-11:39 am

1 stop27h 44m

San José Juan Santamaria Intl

Mon 11/17

1:30 pm-11:05 am

2 stops20h 35m

$379

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sat 1/3

2:30 pm-12:25 pm

1 stop22h 55m

San José Juan Santamaria Intl

Fri 1/9

1:16 am-1:30 pm

1 stop11h 14m

$434

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sat 1/3

2:30 pm-12:25 pm

1 stop22h 55m

San José Juan Santamaria Intl

Sun 1/11

1:19 pm-1:30 pm

1 stop23h 11m

$456

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sat 1/3

2:30 pm-1:05 pm

2 stops23h 35m

San José Juan Santamaria Intl

Sat 1/10

1:16 am-2:56 pm

2 stops12h 40m

$481

Key WestSan José

EYW - SJO

EYWSJO

Key West

Tue 12/2

7:00 am-9:05 pm

1 stop15h 05m

San José Juan Santamaria Intl

Tue 12/9

1:15 pm-11:07 pm

1 stop8h 52m

$494

Key WestSan José

EYW - SJO

EYWSJO

Key West

Tue 12/2

4:18 pm-9:05 pm

1 stop5h 47m

San José Juan Santamaria Intl

Sun 12/7

7:00 am-4:57 pm

1 stop8h 57m

$517

Key WestSan José

EYW - SJO

EYWSJO

Key West

Sat 1/3

2:30 pm-8:40 am

3 stops19h 10m

San José Juan Santamaria Intl

Fri 1/9

1:16 am-1:30 pm

1 stop11h 14m

$518

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Compare providers for flights from Key West to San José

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Key West to San José in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Key West-San José flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Key West-San José flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Key West-San José flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-San José flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-San José flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 30, 2025.
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
7.2
Good
11,034 reviews

Overall

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Crew

8.0

Comfort

7.2

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
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Overall

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Crew

8.0

Comfort

7.2

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 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 $434, Spirit Airlines can have you in San José from Key West in 22h 55m. The distance between Key West and San José is about 1018 mi.

  • What is the cheapest airline to fly from Key West to San José round-trip?

    Currently priced at $535, American Airlines will fly you from Key West to San José and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip.

  • 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
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó
Dominical

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$535Average$643FlexibilityNo cancel feeOn-time71%

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