$589+ Cheap flights from San Jose, CA (SJC) to the Cayman Islands
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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to Cayman Islands with Cheapflights
1. Tell us where you want to go
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Cheapest
Best
Last-minute
One-way
Cheapest flights from San Jose to Cayman IslandsExplore the most affordable flight options available from San Jose to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from San Jose to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Tue 12/2911:00 pm -
2 stops14h 00m
Fri 1/82:25 pm -
2 stops48h 44m
Deal found 10/21![United Airlines logo]()
$740
This Delta deal was found by Cheapflights users on 10/21. 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.
Tue 12/2910:30 pm -
1 stop11h 42m
Fri 1/82:05 pm -
1 stop11h 07m
Deal found 10/21![Delta logo]()
$774
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 12/74:10 pm -
2 stops21h 20m
Mon 12/145:45 pm -
2 stops24h 22m
Deal found 10/23![United Airlines logo]()
$804
This American Airlines deal was found by Cheapflights users on 10/23. 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 12/297:15 pm -
2 stops16h 20m
Fri 1/88:25 am -
2 stops16h 47m
Deal found 10/23![American Airlines logo]()
$824
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 11/234:10 pm -
2 stops21h 20m
Tue 12/15:45 pm -
2 stops46h 28m
Deal found 10/23![United Airlines logo]()
$829
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/2411:00 pm -
1 stop11h 45m
Wed 12/305:45 pm -
2 stops30h 13m
Deal found 10/21![United Airlines logo]()
$842
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Sun 11/224:10 pm -
2 stops45h 20m
Tue 12/15:45 pm -
2 stops45h 14m
Deal found 10/23![United Airlines logo]()
$845
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/242:53 pm -
1 stop20h 57m
Wed 12/303:51 pm -
1 stop10h 35m
Deal found 10/21![American Airlines logo]()
$857
Best flights from San Jose to Cayman IslandsDiscover carefully curated flight deals from San Jose to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from San Jose to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/266:45 pm -
2 stops15h 45m
Mon 3/81:50 pm -
2 stops13h 00m
Deal found 10/20![Southwest logo]()
$589
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 12/2911:00 pm -
2 stops14h 00m
Fri 1/82:25 pm -
2 stops48h 44m
Deal found 10/20![United Airlines logo]()
$740
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 12/2910:30 pm -
1 stop11h 42m
Fri 1/82:05 pm -
1 stop11h 07m
Deal found 10/20![Delta logo]()
$774
This American Airlines deal was found by Cheapflights users on 10/24. 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 12/297:15 pm -
2 stops16h 20m
Fri 1/88:25 am -
2 stops16h 47m
Deal found 10/24![American Airlines logo]()
$824
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 12/74:10 pm -
2 stops21h 20m
Mon 12/145:45 pm -
2 stops24h 22m
Deal found 10/23![United Airlines logo]()
$804
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 11/234:10 pm -
2 stops21h 20m
Tue 12/15:45 pm -
2 stops46h 28m
Deal found 10/23![United Airlines logo]()
$829
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/2411:00 pm -
1 stop11h 45m
Thu 12/315:45 pm -
2 stops32h 00m
Deal found 10/22![United Airlines logo]()
$930
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Mon 11/22:14 pm -
2 stops23h 16m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 10/20![United Airlines logo]()
$948
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/196:00 am -
2 stops27h 05m
Tue 12/13:40 pm -
2 stops22h 28m
Deal found 10/23![American Airlines logo]()
$870
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/196:00 am -
2 stops27h 05m
Mon 11/3012:59 pm -
2 stops29h 47m
Deal found 10/23![American Airlines logo]()
$957
This Mytrip deal was found by Cheapflights users on 10/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:10 pm -
3 stops20h 25m
Sun 11/293:35 pm -
3 stops31h 14m
Deal found 10/23![Multiple Airlines logo]()
$882
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Sun 11/224:10 pm -
2 stops45h 20m
Tue 12/15:45 pm -
2 stops45h 14m
Deal found 10/23![United Airlines logo]()
$845
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/227:26 pm -
2 stops21h 40m
Tue 12/13:40 pm -
2 stops22h 28m
Deal found 10/23![American Airlines logo]()
$994
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/227:26 pm -
2 stops13h 39m
Mon 11/3012:59 pm -
2 stops29h 47m
Deal found 10/23![American Airlines logo]()
$1,080
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 11/234:10 pm -
2 stops21h 20m
Tue 12/15:45 pm -
2 stops46h 28m
Deal found 10/23![United Airlines logo]()
$829
This Delta deal was found by Cheapflights users on 10/23. 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.
Mon 11/239:48 am -
2 stops23h 37m
Tue 12/11:40 pm -
1 stop11h 33m
Deal found 10/23![Delta logo]()
$925
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/2311:56 am -
2 stops29h 10m
Mon 11/3012:59 pm -
2 stops29h 47m
Deal found 10/23![American Airlines logo]()
$980
One-way flights from San Jose to Cayman IslandsSearch for one-way flight options from San Jose to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from San Jose to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/2712:59 pm -
2 stops19h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$892
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/288:48 pm -
2 stops12h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$1,101
This business-class.com deal was found by Cheapflights users on 10/23. 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 business-class.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:48 pm -
1 stop16h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$1,208
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/297:26 pm -
2 stops13h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$1,740
Find flight deals from San Jose to Cayman Islands
Keep the following information in mind while searching for San Jose to Cayman Islands flight deals. Data was last updated October 25, 2026.
Round-trip from | $589 (Southwest) |
|---|
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose to Cayman Islands 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 October 25, 2026.
Use the filters below to find and compare flights from San Jose to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 2/26
6:45 pm-1:30 pm
2 stops15h 45m
George Town Owen Roberts Intl
Mon 3/8
1:50 pm-11:50 pm
2 stops13h 00m
$589
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
11:00 pm-4:00 pm
2 stops14h 00m
George Town Owen Roberts Intl
Fri 1/8
2:25 pm-12:09 pm
2 stops48h 44m
$740
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
10:30 pm-1:12 pm
1 stop11h 42m
George Town Owen Roberts Intl
Fri 1/8
2:05 pm-10:12 pm
1 stop11h 07m
$774
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 12/7
4:10 pm-4:30 pm
2 stops21h 20m
George Town Owen Roberts Intl
Mon 12/14
5:45 pm-3:07 pm
2 stops24h 22m
$804
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
7:15 pm-2:35 pm
2 stops16h 20m
George Town Owen Roberts Intl
Fri 1/8
8:25 am-10:12 pm
2 stops16h 47m
$824
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 11/23
4:10 pm-4:30 pm
2 stops21h 20m
George Town Owen Roberts Intl
Tue 12/1
5:45 pm-1:13 pm
2 stops46h 28m
$829
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 11/27
12:59 pm-11:48 am
2 stops19h 49m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$892
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 12/24
11:00 pm-1:45 pm
1 stop11h 45m
George Town Owen Roberts Intl
Thu 12/31
5:45 pm-10:45 pm
2 stops32h 00m
$930
Quickest round-trip
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sat 11/28
8:48 pm-11:59 am
2 stops12h 11m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$1,101
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sat 11/28
8:48 pm-4:00 pm
1 stop16h 12m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$1,208
Showing 1-10 of 11 resultsSorted by cheapest first
Best time to book a flight from San Jose to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from San Jose with our price prediction graph.
SJC-GCM
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.
Cheapflights Insights
Everything you need to know about your flight from San Jose to the Cayman Islands
SJC-KY0
SJC-GCM
No data available for this route at this time. Please check back soon.
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