$603+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Nov 16 — Nov 231
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 October 17, 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 17, 2026.
This Southwest deal was found by Cheapflights users on 10/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:30 pm -
2 stops14h 05m
Fri 1/81:50 pm -
2 stops21h 05m
Deal found 10/12![Southwest logo]()
$626
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/272:55 pm -
1 stop20h 40m
Fri 12/43:45 pm -
2 stops23h 27m
Deal found 10/13![American Airlines logo]()
$639
This Southwest deal was found by Cheapflights users on 10/13. 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 11/277:30 pm -
2 stops14h 55m
Fri 12/41:30 pm -
2 stops21h 15m
Deal found 10/13![Southwest logo]()
$649
This Delta deal was found by Cheapflights users on 10/16. 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.
Mon 11/3010:40 pm -
1 stop10h 45m
Mon 12/71:40 pm -
1 stop11h 33m
Deal found 10/16![Delta logo]()
$670
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Mon 11/24:14 pm -
2 stops16h 41m
Thu 11/512:18 pm -
2 stops13h 23m
Deal found 10/13![American Airlines logo]()
$695
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2010:30 pm -
1 stop13h 06m
Tue 12/292:27 pm -
1 stop11h 32m
Deal found 10/17![Delta logo]()
$719
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/22:14 pm -
2 stops23h 16m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 10/12![United Airlines logo]()
$728
This United Airlines deal was found by Cheapflights users on 10/13. 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 12/298:30 am -
2 stops26h 15m
Fri 1/82:55 pm -
2 stops25h 26m
Deal found 10/13![United Airlines logo]()
$756
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2110:30 pm -
1 stop11h 42m
Tue 12/292:27 pm -
1 stop11h 32m
Deal found 10/17![Delta logo]()
$768
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 17, 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 17, 2026.
This Southwest deal was found by Cheapflights users on 10/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:30 pm -
2 stops14h 05m
Fri 1/81:50 pm -
2 stops21h 05m
Deal found 10/12![Southwest logo]()
$626
This Delta deal was found by Cheapflights users on 10/16. 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.
Mon 11/3010:40 pm -
1 stop10h 45m
Mon 12/71:40 pm -
1 stop11h 33m
Deal found 10/16![Delta logo]()
$670
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 12/2111:00 pm -
2 stops14h 00m
Wed 12/305:45 pm -
2 stops32h 00m
Deal found 10/12![United Airlines logo]()
$784
This Southwest deal was found by Cheapflights users on 10/13. 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 4/99:25 pm -
1 stop15h 15m
Fri 4/161:05 pm -
2 stops20h 40m
Deal found 10/13![Southwest logo]()
$654
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2310:30 pm -
1 stop11h 42m
Tue 12/293:51 pm -
2 stops20h 15m
Deal found 10/17![Delta logo]()
$723
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 12/298:30 am -
2 stops26h 15m
Fri 1/82:55 pm -
2 stops25h 26m
Deal found 10/14![United Airlines logo]()
$822
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2010:30 pm -
1 stop13h 06m
Wed 12/303:51 pm -
1 stop10h 08m
Deal found 10/17![Delta logo]()
$818
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Mon 11/22:14 pm -
2 stops23h 16m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 10/13![United Airlines logo]()
$825
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2310:30 pm -
1 stop13h 06m
Thu 12/311:13 pm -
2 stops22h 53m
Deal found 10/17![Delta logo]()
$822
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 17, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Mon 11/24:14 pm -
2 stops16h 41m
Thu 11/512:18 pm -
2 stops13h 23m
Deal found 10/13![American Airlines logo]()
$695
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/22:14 pm -
2 stops23h 16m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 10/12![United Airlines logo]()
$728
This Mytrip deal was found by Cheapflights users on 10/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:41 pm -
3 stops22h 24m
Thu 11/54:45 pm -
3 stops30h 27m
Deal found 10/13![Multiple Airlines logo]()
$856
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/272:55 pm -
1 stop20h 40m
Fri 12/43:45 pm -
2 stops23h 27m
Deal found 10/13![American Airlines logo]()
$639
This Southwest deal was found by Cheapflights users on 10/13. 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 11/277:30 pm -
2 stops14h 55m
Fri 12/41:30 pm -
2 stops21h 15m
Deal found 10/13![Southwest logo]()
$649
This Delta deal was found by Cheapflights users on 10/16. 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.
Mon 11/3010:40 pm -
1 stop10h 45m
Mon 12/71:40 pm -
1 stop11h 33m
Deal found 10/16![Delta logo]()
$670
This Mytrip deal was found by Cheapflights users on 10/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:10 pm -
3 stops21h 55m
Mon 12/73:50 pm -
3 stops28h 19m
Deal found 10/16![Multiple Airlines logo]()
$921
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 17, 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 17, 2026.
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:14 pm -
2 stops23h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$603
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:30 am -
2 stops31h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$644
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:10 pm -
2 stops45h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$645
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/272:14 pm -
2 stops20h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$858
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/296:00 am -
2 stops27h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$872
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/304:10 pm -
2 stops21h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$903
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2810:10 am -
2 stops22h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$954
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/272:55 pm -
1 stop22h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$1,233
This Delta deal was found by Cheapflights users on 10/16. 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.
Sat 11/2810:40 pm -
1 stop10h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$2,344
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 17, 2026.
Round-trip from | $626 (Southwest) |
|---|---|
One-way from | $603 (United Airlines) |
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 17, 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
Wed 11/25
2:14 pm-4:30 pm
2 stops23h 16m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$603
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
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
$626
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/1
4:10 pm-4:30 pm
2 stops45h 20m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$645
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 4/9
9:25 pm-2:40 pm
1 stop15h 15m
George Town Owen Roberts Intl
Fri 4/16
1:05 pm-7:45 am
2 stops20h 40m
$654
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 11/30
10:40 pm-12:25 pm
1 stop10h 45m
George Town Owen Roberts Intl
Mon 12/7
1:40 pm-10:13 pm
1 stop11h 33m
$670
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Wed 12/23
10:30 pm-1:12 pm
1 stop11h 42m
George Town Owen Roberts Intl
Tue 12/29
3:51 pm-9:06 am
2 stops20h 15m
$723
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 12/21
11:00 pm-4:00 pm
2 stops14h 00m
George Town Owen Roberts Intl
Wed 12/30
5:45 pm-10:45 pm
2 stops32h 00m
$784
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sun 12/20
10:30 pm-2:36 pm
1 stop13h 06m
George Town Owen Roberts Intl
Wed 12/30
3:51 pm-10:59 pm
1 stop10h 08m
$818
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
8:30 am-1:45 pm
2 stops26h 15m
George Town Owen Roberts Intl
Fri 1/8
2:55 pm-1:21 pm
2 stops25h 26m
$822
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Wed 12/23
10:30 pm-2:36 pm
1 stop13h 06m
George Town Owen Roberts Intl
Thu 12/31
1:13 pm-9:06 am
2 stops22h 53m
$822
Showing 1-10 of 14 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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