$192+ Cheap flights from Key West (EYW) to San José (SJO)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJO
May 19 — May 261
Round-trip
1 adult, Economy
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Find cheap flights from Key West to San José with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Key West to San José
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Cheapest flights from Key West to San JoséExplore 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 19, 2026.
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 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 6/263:25 pm
EYW
- SJO
1 stop18h 55m
Multiple Airlines
Sat 7/119:35 am
SJO
- EYW
1 stop25h 13m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 6/263:25 pm
EYW
- SJO
1 stop18h 55m
Multiple Airlines
Wed 7/157:07 am
SJO
- EYW
1 stop27h 41m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 6/263:25 pm
EYW
- SJO
1 stop18h 55m
Multiple Airlines
Thu 7/169:35 am
SJO
- EYW
1 stop27h 02m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 6/263:25 pm
EYW
- SJO
1 stop18h 55m
Multiple Airlines
Sun 7/129:35 am
SJO
- EYW
2 stops22h 06m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Wed 7/15:10 pm
EYW
- SJO
2 stops21h 05m
Multiple Airlines
Sat 7/119:35 am
SJO
- EYW
1 stop25h 13m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Thu 7/28:48 pm
EYW
- SJO
1 stop20h 23m
Multiple Airlines
Sat 7/119:35 am
SJO
- EYW
1 stop25h 13m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Sun 6/289:16 pm
EYW
- SJO
1 stop19h 55m
Multiple Airlines
Sat 7/119:35 am
SJO
- EYW
1 stop25h 13m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 6/263:25 pm
EYW
- SJO
1 stop18h 55m
Multiple Airlines
Fri 7/101:21 pm
SJO
- EYW
2 stops22h 33m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Thu 7/27:56 pm
EYW
- SJO
2 stops18h 19m
Multiple Airlines
Wed 7/157:07 am
SJO
- EYW
1 stop27h 41m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Sun 6/289:16 pm
EYW
- SJO
1 stop19h 55m
Multiple Airlines
Wed 7/157:07 am
SJO
- EYW
1 stop27h 41m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$462
Best flights from Key West to San JoséDiscover carefully curated flight deals from Key West to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
Discover carefully curated flight deals from Key West to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sun 5/249:24 pm
EYW
- SJO
1 stop19h 54m
Multiple Airlines
Sat 5/307:00 am
SJO
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$488
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/68:05 am
EYW
- SJO
2 stops13h 02m
American Airlines
Wed 5/136:30 am
SJO
- EYW
2 stops14h 06m
American Airlines
Deal found 4/14![American Airlines logo]()
$641
This United Airlines deal was found by Cheapflights users on 4/14. 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 5/74:47 pm
EYW
- SJO
1 stop21h 34m
United Airlines
Sun 5/107:55 am
SJO
- EYW
1 stop30h 07m
United Airlines
Deal found 4/14![United Airlines logo]()
$991
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/611:46 am
EYW
- SJO
2 stops25h 59m
Multiple Airlines
Wed 5/137:00 am
SJO
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$536
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:24 pm
EYW
- SJO
1 stop19h 25m
Delta
Mon 7/131:16 pm
SJO
- EYW
1 stop28h 35m
Delta
Deal found 4/16![Delta logo]()
$1,150
This Kiwi.com deal was found by Cheapflights users on 4/18. 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
Wed 5/137:00 am
SJO
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$546
This American Airlines deal was found by Cheapflights users on 4/15. 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 5/237:29 pm
EYW
- SJO
2 stops19h 40m
American Airlines
Sat 5/3012:50 pm
SJO
- EYW
2 stops21h 26m
American Airlines
Deal found 4/15![American Airlines logo]()
$684
This American Airlines deal was found by Cheapflights users on 4/15. 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.
Sun 5/247:40 pm
EYW
- SJO
2 stops19h 19m
American Airlines
Sat 5/3012:50 pm
SJO
- EYW
2 stops21h 26m
American Airlines
Deal found 4/15![American Airlines logo]()
$762
Last-minute flights from Key West to San JoséDiscover last-minute flight deals from Key West to San José. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to San José. Data last updated April 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Wed 4/2211:51 am
EYW
- SJO
1 stop29h 27m
Multiple Airlines
Tue 5/195:50 am
SJO
- EYW
2 stops27h 16m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$596
This American Airlines deal was found by Cheapflights users on 4/14. 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 4/228:05 am
EYW
- SJO
2 stops13h 02m
American Airlines
Wed 4/296:30 am
SJO
- EYW
2 stops14h 06m
American Airlines
Deal found 4/14![American Airlines logo]()
$641
This American Airlines deal was found by Cheapflights users on 4/17. 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 4/2411:24 am
EYW
- SJO
1 stop9h 43m
American Airlines
Sat 5/26:30 am
SJO
- EYW
1 stop8h 00m
American Airlines
Deal found 4/17![American Airlines logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 4/18. 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
Wed 5/137:00 am
SJO
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/611:46 am
EYW
- SJO
2 stops25h 59m
Multiple Airlines
Wed 5/137:00 am
SJO
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$536
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/611:24 am
EYW
- SJO
1 stop9h 43m
American Airlines
Wed 5/132:31 pm
SJO
- EYW
1 stop6h 27m
American Airlines
Deal found 4/14![American Airlines logo]()
$636
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/232:48 pm
EYW
- SJO
2 stops22h 57m
Multiple Airlines
Sat 5/307:00 am
SJO
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sun 5/249:24 pm
EYW
- SJO
1 stop19h 54m
Multiple Airlines
Sat 5/307:00 am
SJO
- EYW
1 stop26h 25m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$488
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sun 5/249:24 pm
EYW
- SJO
1 stop19h 54m
Multiple Airlines
Sun 5/317:00 am
SJO
- EYW
1 stop29h 01m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$501
One-way flights from Key West to San JoséSearch for one-way flight options from Key West to San José. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
Search for one-way flight options from Key West to San José. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/611:46 am
EYW
- SJO
2 stops25h 59m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$192
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/66:45 am
EYW
- SJO
1 stop8h 23m
American Airlines
Deal found 4/14![American Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 4/17. 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 4/248:05 am
EYW
- SJO
2 stops13h 02m
American Airlines
Deal found 4/17![American Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Fri 4/246:22 pm
EYW
- SJO
3 stops19h 59m
United Airlines
Deal found 4/17![United Airlines logo]()
$1,932
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 19, 2026.
Round-trip from | $358 (Kiwi.com) |
|---|---|
One-way from | $192 (Kiwi.com) |
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 19, 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
Cheapest round-trip
Key WestSan José
EYW - SJO
EYWSJO
Key West
Sun 5/24
9:24 pm-3:18 pm
1 stop19h 54m
San José Juan Santamaria Intl
Sat 5/30
7:00 am-11:25 am
1 stop26h 25m
$488
Key WestSan José
EYW - SJO
EYWSJO
Key West
Wed 5/6
11:46 am-11:45 am
2 stops25h 59m
San José Juan Santamaria Intl
Wed 5/13
7:00 am-11:25 am
1 stop26h 25m
$536
Key WestSan José
EYW - SJO
EYWSJO
Key West
Wed 4/29
11:51 am-3:18 pm
1 stop29h 27m
San José Juan Santamaria Intl
Wed 5/13
7:00 am-11:25 am
1 stop26h 25m
$546
Quickest round-trip
Key WestSan José
EYW - SJO
EYWSJO
Key West
Wed 5/6
8:05 am-7:07 pm
2 stops13h 02m
San José Juan Santamaria Intl
Wed 5/13
6:30 am-10:36 pm
2 stops14h 06m
$641
Key WestSan José
EYW - SJO
EYWSJO
Key West
Sat 5/23
7:29 pm-1:09 pm
2 stops19h 40m
San José Juan Santamaria Intl
Sat 5/30
12:50 pm-12:16 pm
2 stops21h 26m
$684
Key WestSan José
EYW - SJO
EYWSJO
Key West
Sun 5/24
7:40 pm-12:59 pm
2 stops19h 19m
San José Juan Santamaria Intl
Sat 5/30
12:50 pm-12:16 pm
2 stops21h 26m
$762
Key WestSan José
EYW - SJO
EYWSJO
Key West
Thu 5/7
4:47 pm-12:21 pm
1 stop21h 34m
San José Juan Santamaria Intl
Sun 5/10
7:55 am-4:02 pm
1 stop30h 07m
$991
Key WestSan José
EYW - SJO
EYWSJO
Key West
Fri 6/26
6:24 pm-11:49 am
1 stop19h 25m
San José Juan Santamaria Intl
Mon 7/13
1:16 pm-7:51 pm
1 stop28h 35m
$1,150
Cheapest one-way
Key WestSan José
EYW - SJO
EYWSJO
Key West
Wed 5/6
11:46 am-11:45 am
2 stops25h 59m
$192
Quickest one-way
Key WestSan José
EYW - SJO
EYWSJO
Key West
Wed 5/6
6:45 am-1:08 pm
1 stop8h 23m
$360
Showing 1-10 of 12 resultsSorted 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.
EYW-SJO
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 19, 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.
Entertainment
6.9
Comfort
7.2
Overall
7.1
Food
6.4
Boarding
7.5
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
Entertainment
6.9
Comfort
7.2
Overall
7.1
Food
6.4
Boarding
7.5
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
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.
Traveling to a place near San José?
Book flights to San José if you plan to visit one of these locationsAlajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio
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Key West and San José flights
Browse other Key West and San José flight options. Last updated on April 19, 2026.
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Popular flight searches
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Other flights to San José
Explore flights to San José departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 19, 2026.
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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$523 | Average$747 | FlexibilityNo cancel fee | On-time71% |