$320+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJO
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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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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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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/3. 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 11/1811:14 am -
1 stop10h 36m
Wed 12/23:54 pm -
2 stops25h 53m
Deal found 9/3![American Airlines logo]()
$613
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/2210:59 am -
1 stop6h 12m
Thu 10/297:07 am -
1 stop25h 12m
Deal found 9/7![Multiple Airlines logo]()
$665
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/810:59 am -
1 stop6h 12m
Wed 10/148:55 am -
1 stop24h 26m
Deal found 9/3![Multiple Airlines logo]()
$670
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/2110:24 am -
1 stop11h 57m
Wed 11/42:07 pm -
2 stops18h 41m
Deal found 9/3![American Airlines logo]()
$688
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1810:59 am -
1 stop6h 12m
Sun 11/17:00 am -
1 stop26h 19m
Deal found 9/3![Multiple Airlines logo]()
$713
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Mon 10/197:19 pm -
2 stops27h 02m
Mon 10/263:01 pm -
2 stops23h 10m
Deal found 9/4![American Airlines logo]()
$718
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/184:45 pm -
2 stops21h 15m
Sun 11/12:01 pm -
2 stops22h 02m
Deal found 9/3![American Airlines logo]()
$723
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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. 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 2/127:00 am -
1 stop14h 51m
Fri 2/193:56 pm -
2 stops19h 11m
Deal found 9/5![American Airlines logo]()
$643
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/810:59 am -
1 stop6h 12m
Wed 10/148:55 am -
1 stop24h 26m
Deal found 9/4![Multiple Airlines logo]()
$700
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/2110:24 am -
1 stop11h 57m
Wed 11/43:54 pm -
1 stop16h 54m
Deal found 9/3![American Airlines logo]()
$690
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Mon 10/191:43 pm -
1 stop8h 38m
Mon 10/266:00 am -
1 stop8h 58m
Deal found 9/4![American Airlines logo]()
$713
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/225:28 pm -
1 stop4h 53m
Thu 10/296:00 am -
2 stops28h 27m
Deal found 9/7![American Airlines logo]()
$718
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/184:45 pm -
2 stops21h 15m
Sun 11/12:01 pm -
2 stops22h 02m
Deal found 9/3![American Airlines logo]()
$723
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/111:30 am -
1 stop10h 37m
Tue 10/66:00 am -
1 stop11h 33m
Deal found 9/3![American Airlines logo]()
$788
Last-minute flights from Key West to San JoséDiscover last-minute flight deals from Key West to San José. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to San José. Data last updated September 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/7. 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 9/2911:30 am -
1 stop10h 37m
Fri 10/26:00 am -
1 stop11h 17m
Deal found 9/7![American Airlines logo]()
$789
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/111:30 am -
1 stop10h 37m
Tue 10/66:00 am -
1 stop11h 33m
Deal found 9/3![American Airlines logo]()
$788
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/810:59 am -
1 stop6h 12m
Wed 10/148:55 am -
1 stop24h 26m
Deal found 9/3![Multiple Airlines logo]()
$670
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1810:59 am -
1 stop6h 12m
Sun 11/17:00 am -
1 stop26h 19m
Deal found 9/3![Multiple Airlines logo]()
$713
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/184:45 pm -
2 stops21h 15m
Sun 11/12:01 pm -
2 stops22h 02m
Deal found 9/3![American Airlines logo]()
$723
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Mon 10/197:19 pm -
2 stops27h 02m
Mon 10/263:01 pm -
2 stops23h 10m
Deal found 9/4![American Airlines logo]()
$718
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/2110:24 am -
1 stop11h 57m
Wed 11/42:07 pm -
2 stops18h 41m
Deal found 9/3![American Airlines logo]()
$688
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/2210:59 am -
1 stop6h 12m
Thu 10/297:07 am -
1 stop25h 12m
Deal found 9/7![Multiple Airlines logo]()
$665
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 September 8, 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 September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 2/710:59 am -
2 stops14h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Mon 9/2812:59 pm -
3 stops44h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Mon 9/286:27 pm -
2 stops20h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$448
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 September 8, 2026.
Round-trip from | $613 (American Airlines) |
|---|---|
One-way from | $320 (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 7,457,451 searches. Data last updated September 8, 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
Quickest round-trip
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Sun 2/7
10:59 am-11:59 pm
2 stops14h 00m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$320
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Mon 9/28
7:47 pm-8:07 pm
1 stop26h 20m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$456
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Fri 2/12
7:00 am-8:51 pm
1 stop14h 51m
San José Juan Santamaria Intl
Fri 2/19
3:56 pm-12:07 pm
2 stops19h 11m
$643
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Wed 10/21
10:24 am-8:21 pm
1 stop11h 57m
San José Juan Santamaria Intl
Wed 11/4
3:54 pm-9:48 am
1 stop16h 54m
$690
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Thu 10/8
10:59 am-3:11 pm
1 stop6h 12m
San José Juan Santamaria Intl
Wed 10/14
8:55 am-11:21 am
1 stop24h 26m
$700
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Mon 10/19
1:43 pm-8:21 pm
1 stop8h 38m
San José Juan Santamaria Intl
Mon 10/26
6:00 am-4:58 pm
1 stop8h 58m
$713
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Thu 10/22
5:28 pm-8:21 pm
1 stop4h 53m
San José Juan Santamaria Intl
Thu 10/29
6:00 am-12:27 pm
2 stops28h 27m
$718
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Sun 10/18
4:45 pm-12:00 pm
2 stops21h 15m
San José Juan Santamaria Intl
Sun 11/1
2:01 pm-1:03 pm
2 stops22h 02m
$723
Key WestSan José
EYW Key West - SJO San José Juan Santamaria Intl
EYWSJO
Key West
Thu 10/1
11:30 am-8:07 pm
1 stop10h 37m
San José Juan Santamaria Intl
Tue 10/6
6:00 am-7:33 pm
1 stop11h 33m
$788
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.
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 September 8, 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.
Comfort
7.2
Food
6.4
Entertainment
6.8
Crew
7.9
Boarding
7.5
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Comfort
7.2
Food
6.4
Entertainment
6.8
Crew
7.9
Boarding
7.5
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
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
Jacó
Heredia
Dominical
Manuel Antonio
Browse thousands of different options on Cheapflights for your next trip
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Key West and San José flights
Browse other Key West and San José flight options. Last updated on September 8, 2026.
Other flights from Key West
Browse through other flights departing from Key West. Flights are based on user searches made on Cheapflights and were last updated on September 8, 2026.
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 September 8, 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 7,457,451 searches. Data last updated September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$523 | Average$747 | FlexibilityNo cancel fee | On-time71% |