$572+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Oct 23 — Oct 301
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
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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Best
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 September 23, 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 September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:30 pm -
2 stops14h 05m
Mon 11/161:30 pm -
2 stops21h 00m
Deal found 9/22![Southwest logo]()
$572
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Wed 11/44:10 pm -
2 stops21h 20m
Wed 11/115:45 pm -
2 stops21h 17m
Deal found 9/20![United Airlines logo]()
$598
This Delta deal was found by Cheapflights users on 9/20. 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.
Fri 12/410:30 pm -
1 stop11h 13m
Sat 12/122:08 pm -
1 stop11h 05m
Deal found 9/20![Delta logo]()
$629
This Delta deal was found by Cheapflights users on 9/20. 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.
Fri 12/42:54 pm -
2 stops18h 49m
Sun 12/131:40 pm -
2 stops24h 01m
Deal found 9/20![Delta logo]()
$634
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Mon 11/24:10 pm -
2 stops21h 20m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 9/22![United Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Sat 11/78:45 am -
2 stops25h 30m
Sat 11/145:45 pm -
2 stops21h 17m
Deal found 9/23![United Airlines logo]()
$764
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 12/42:11 pm -
2 stops22h 49m
Mon 12/145:45 pm -
2 stops30h 08m
Deal found 9/20![United Airlines logo]()
$774
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:19 pm -
2 stops13h 47m
Fri 1/83:52 pm -
2 stops22h 18m
Deal found 9/18![American Airlines logo]()
$784
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Tue 12/298:30 am -
2 stops29h 05m
Fri 1/82:55 pm -
2 stops33h 16m
Deal found 9/22![United Airlines logo]()
$786
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 12/42:11 pm -
2 stops22h 49m
Sun 12/132:25 pm -
2 stops24h 34m
Deal found 9/20![United Airlines logo]()
$812
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 September 23, 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 September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:30 pm -
2 stops14h 05m
Mon 11/161:30 pm -
2 stops21h 00m
Deal found 9/22![Southwest logo]()
$572
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Wed 11/44:10 pm -
2 stops21h 20m
Wed 11/115:45 pm -
2 stops21h 17m
Deal found 9/20![United Airlines logo]()
$598
This Delta deal was found by Cheapflights users on 9/20. 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.
Fri 12/410:30 pm -
1 stop11h 13m
Sat 12/122:08 pm -
2 stops21h 50m
Deal found 9/20![Delta logo]()
$634
This American Airlines deal was found by Cheapflights users on 9/19. 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 12/292:53 pm -
1 stop20h 57m
Fri 1/84:07 pm -
2 stops22h 04m
Deal found 9/19![American Airlines logo]()
$870
This Delta deal was found by Cheapflights users on 9/20. 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.
Fri 12/42:54 pm -
2 stops18h 49m
Sun 12/131:40 pm -
2 stops24h 01m
Deal found 9/20![Delta logo]()
$634
This United Airlines deal was found by Cheapflights users on 9/20. 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 11/24:10 pm -
2 stops21h 20m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 9/20![United Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Tue 12/298:30 am -
2 stops29h 05m
Fri 1/82:55 pm -
2 stops33h 16m
Deal found 9/22![United Airlines logo]()
$786
This Delta deal was found by Cheapflights users on 9/20. 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 stop9h 53m
Deal found 9/20![Delta logo]()
$845
This Delta deal was found by Cheapflights users on 9/20. 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.
Sat 12/56:30 am -
1 stop26h 55m
Sat 12/122:08 pm -
1 stop11h 05m
Deal found 9/20![Delta logo]()
$856
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 September 23, 2026.
Round-trip from | $572 (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 September 23, 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
Thu 11/12
7:30 pm-12:35 pm
2 stops14h 05m
George Town Owen Roberts Intl
Mon 11/16
1:30 pm-7:30 am
2 stops21h 00m
$572
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Wed 11/4
4:10 pm-4:30 pm
2 stops21h 20m
George Town Owen Roberts Intl
Wed 11/11
5:45 pm-12:02 pm
2 stops21h 17m
$598
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 12/4
10:30 pm-12:43 pm
1 stop11h 13m
George Town Owen Roberts Intl
Sat 12/12
2:08 pm-8:58 am
2 stops21h 50m
$634
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 12/4
2:54 pm-12:43 pm
2 stops18h 49m
George Town Owen Roberts Intl
Sun 12/13
1:40 pm-10:41 am
2 stops24h 01m
$634
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 11/2
4:10 pm-4:30 pm
2 stops21h 20m
George Town Owen Roberts Intl
Thu 11/5
5:45 pm-10:59 pm
2 stops32h 14m
$692
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
8:30 am-4:35 pm
2 stops29h 05m
George Town Owen Roberts Intl
Fri 1/8
2:55 pm-9:11 pm
2 stops33h 16m
$786
Quickest round-trip
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-8:58 pm
1 stop9h 53m
$845
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sat 12/5
6:30 am-12:25 pm
1 stop26h 55m
George Town Owen Roberts Intl
Sat 12/12
2:08 pm-10:13 pm
1 stop11h 05m
$856
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
2:53 pm-2:50 pm
1 stop20h 57m
George Town Owen Roberts Intl
Fri 1/8
4:07 pm-11:11 am
2 stops22h 04m
$870
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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