$331+ Cheap flights from San Jose, CA (SJC) to the Cayman Islands
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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Aug 15 — Aug 221
Round-trip
1 adult, Economy
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Find cheap flights from San Jose to Cayman Islands with Cheapflights
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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 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 July 16, 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 July 16, 2026.
This Southwest deal was found by Cheapflights users on 7/13. 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.
Tue 12/297:30 pm
SJC
- GCM
2 stops14h 05m
Southwest
Thu 1/71:50 pm
GCM
- SJC
2 stops21h 10m
Southwest
Deal found 7/13![Southwest logo]()
$682
This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 11/126:10 pm
SJC
- GCM
2 stops15h 25m
Southwest
Mon 11/161:30 pm
GCM
- SJC
2 stops21h 05m
Southwest
Deal found 7/13![Southwest logo]()
$692
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Mon 10/264:11 pm
SJC
- GCM
2 stops16h 44m
American Airlines
Sun 11/19:00 am
GCM
- SJC
2 stops16h 16m
American Airlines
Deal found 7/15![American Airlines logo]()
$721
This United Airlines deal was found by Cheapflights users on 7/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/292:19 pm
SJC
- GCM
2 stops23h 16m
United Airlines
Thu 1/72:50 pm
GCM
- SJC
1 stop10h 46m
United Airlines
Deal found 7/15![United Airlines logo]()
$759
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2910:20 pm
SJC
- GCM
1 stop11h 20m
Delta
Fri 1/82:05 pm
GCM
- SJC
1 stop9h 53m
Delta
Deal found 7/15![Delta logo]()
$801
This United Airlines deal was found by Cheapflights users on 7/12. 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 10/252:12 pm
SJC
- GCM
2 stops23h 18m
United Airlines
Thu 10/294:45 pm
GCM
- SJC
2 stops32h 06m
United Airlines
Deal found 7/12![United Airlines logo]()
$816
This American Airlines deal was found by Cheapflights users on 7/12. 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 7/2312:39 pm
SJC
- GCM
2 stops20h 21m
American Airlines
Mon 7/275:10 pm
GCM
- SJC
2 stops20h 54m
American Airlines
Deal found 7/12![American Airlines logo]()
$817
This Delta deal was found by Cheapflights users on 7/13. 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 12/2910:20 pm
SJC
- GCM
1 stop13h 10m
Delta
Thu 1/72:05 pm
GCM
- SJC
1 stop9h 53m
Delta
Deal found 7/13![Delta logo]()
$821
This Delta deal was found by Cheapflights users on 7/13. 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.
Thu 11/123:00 pm
SJC
- GCM
2 stops18h 25m
Delta
Mon 11/161:50 pm
GCM
- SJC
1 stop12h 08m
Delta
Deal found 7/13![Delta logo]()
$826
This United Airlines deal was found by Cheapflights users on 7/13. 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 12/292:19 pm
SJC
- GCM
3 stops47h 16m
United Airlines
Fri 1/82:50 pm
GCM
- SJC
2 stops25h 36m
United Airlines
Deal found 7/13![United Airlines logo]()
$839
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 July 16, 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 July 16, 2026.
This Southwest deal was found by Cheapflights users on 7/11. 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.
Tue 12/297:30 pm
SJC
- GCM
2 stops14h 05m
Southwest
Fri 1/81:50 pm
GCM
- SJC
2 stops21h 05m
Southwest
Deal found 7/11![Southwest logo]()
$682
This Delta deal was found by Cheapflights users on 7/11. 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 12/2910:20 pm
SJC
- GCM
1 stop13h 10m
Delta
Thu 1/72:05 pm
GCM
- SJC
1 stop9h 53m
Delta
Deal found 7/11![Delta logo]()
$801
This United Airlines deal was found by Cheapflights users on 7/12. 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 10/252:12 pm
SJC
- GCM
2 stops23h 18m
United Airlines
Thu 10/294:45 pm
GCM
- SJC
2 stops32h 06m
United Airlines
Deal found 7/12![United Airlines logo]()
$816
This Southwest deal was found by Cheapflights users on 7/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/298:25 pm
SJC
- GCM
2 stops13h 10m
Southwest
Thu 1/71:50 pm
GCM
- SJC
2 stops21h 10m
Southwest
Deal found 7/15![Southwest logo]()
$682
This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 11/126:10 pm
SJC
- GCM
2 stops15h 25m
Southwest
Mon 11/161:30 pm
GCM
- SJC
2 stops21h 05m
Southwest
Deal found 7/13![Southwest logo]()
$692
This Delta deal was found by Cheapflights users on 7/13. 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.
Thu 11/123:00 pm
SJC
- GCM
2 stops18h 25m
Delta
Mon 11/161:50 pm
GCM
- SJC
1 stop12h 08m
Delta
Deal found 7/13![Delta logo]()
$826
This United Airlines deal was found by Cheapflights users on 7/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/298:38 am
SJC
- GCM
2 stops26h 04m
United Airlines
Thu 1/72:50 pm
GCM
- SJC
1 stop10h 46m
United Airlines
Deal found 7/15![United Airlines logo]()
$836
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated July 16, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated July 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/13. 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 7/179:40 pm
SJC
- GCM
1 stop10h 50m
Southwest
Fri 7/2412:50 pm
GCM
- SJC
2 stops12h 40m
Southwest
Deal found 7/13![Southwest logo]()
$867
This American Airlines deal was found by Cheapflights users on 7/13. 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 7/177:23 pm
SJC
- GCM
2 stops17h 40m
American Airlines
Fri 7/245:10 pm
GCM
- SJC
2 stops19h 39m
American Airlines
Deal found 7/13![American Airlines logo]()
$872
This Delta deal was found by Cheapflights users on 7/13. 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 7/1710:00 pm
SJC
- GCM
1 stop11h 31m
Delta
Fri 7/2412:56 pm
GCM
- SJC
1 stop11h 53m
Delta
Deal found 7/13![Delta logo]()
$1,161
This American Airlines deal was found by Cheapflights users on 7/12. 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 7/2312:39 pm
SJC
- GCM
2 stops20h 21m
American Airlines
Mon 7/275:10 pm
GCM
- SJC
2 stops20h 54m
American Airlines
Deal found 7/12![American Airlines logo]()
$817
This American Airlines deal was found by Cheapflights users on 7/12. 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 8/22:23 pm
SJC
- GCM
2 stops19h 02m
American Airlines
Sun 8/912:00 pm
GCM
- SJC
2 stops24h 50m
American Airlines
Deal found 7/12![American Airlines logo]()
$801
This Delta deal was found by Cheapflights users on 7/12. 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.
Sun 8/210:00 pm
SJC
- GCM
1 stop11h 39m
Delta
Sun 8/91:04 pm
GCM
- SJC
1 stop11h 54m
Delta
Deal found 7/12![Delta logo]()
$1,335
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:12 pm
SJC
- GCM
2 stops15h 27m
Delta
Mon 8/171:04 pm
GCM
- SJC
1 stop11h 54m
Delta
Deal found 7/15![Delta logo]()
$1,116
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 July 16, 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 July 16, 2026.
This Southwest deal was found by Cheapflights users on 7/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:10 pm
SJC
- GCM
2 stops14h 45m
Southwest
Deal found 7/14![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 7/14. 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 7/301:10 pm
SJC
- GCM
1 stop21h 20m
United Airlines
Deal found 7/14![United Airlines logo]()
$608
This KAYAK deal was found by Cheapflights users on 7/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/303:15 pm
SJC
- GCM
3 stops46h 55m
British Airways
Deal found 7/14![British Airways logo]()
$5,619
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 July 16, 2026.
Round-trip from | $682 (Southwest) |
|---|---|
One-way from | $331 (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 2,558,603 searches. Data last updated July 16, 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 - GCM
SJCGCM
San Jose
Tue 12/29
7:30 pm-12:35 pm
2 stops14h 05m
George Town Owen Roberts Intl
Fri 1/8
1:50 pm-7:55 am
2 stops21h 05m
$682
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Tue 12/29
8:25 pm-12:35 pm
2 stops13h 10m
George Town Owen Roberts Intl
Thu 1/7
1:50 pm-8:00 am
2 stops21h 10m
$682
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Thu 11/12
6:10 pm-12:35 pm
2 stops15h 25m
George Town Owen Roberts Intl
Mon 11/16
1:30 pm-7:35 am
2 stops21h 05m
$692
Quickest round-trip
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Tue 12/29
10:20 pm-2:30 pm
1 stop13h 10m
George Town Owen Roberts Intl
Thu 1/7
2:05 pm-8:58 pm
1 stop9h 53m
$801
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Sun 10/25
2:12 pm-3:30 pm
2 stops23h 18m
George Town Owen Roberts Intl
Thu 10/29
4:45 pm-10:51 pm
2 stops32h 06m
$816
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Thu 11/12
3:00 pm-12:25 pm
2 stops18h 25m
George Town Owen Roberts Intl
Mon 11/16
1:50 pm-10:58 pm
1 stop12h 08m
$826
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Tue 12/29
8:38 am-1:42 pm
2 stops26h 04m
George Town Owen Roberts Intl
Thu 1/7
2:50 pm-10:36 pm
1 stop10h 46m
$836
Cheapest one-way
Quickest one-way
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Thu 7/30
7:10 pm-11:55 am
2 stops14h 45m
$331
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Thu 7/30
3:15 pm-4:10 pm
3 stops46h 55m
$5,619
Sorted 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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