$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 29 — Nov 51
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from San Jose to Cayman Islands
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Best
Last-minute
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 29, 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 29, 2026.
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/127:10 pm -
2 stops13h 13m
Thu 11/198:23 am -
2 stops13h 23m
Deal found 9/28![American Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 9/28. 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 11/1210:40 pm -
1 stop10h 45m
Thu 11/191:40 pm -
1 stop11h 32m
Deal found 9/28![Delta logo]()
$598
This United Airlines deal was found by Cheapflights users on 9/27. 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 stops30h 23m
Deal found 9/27![United Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 9/28. 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 11/64:10 pm -
2 stops21h 25m
Tue 11/105:45 pm -
2 stops21h 17m
Deal found 9/28![United Airlines logo]()
$728
This American Airlines deal was found by Cheapflights users on 9/25. 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 stops16h 16m
Fri 1/88:25 am -
2 stops16h 47m
Deal found 9/25![American Airlines logo]()
$753
This United Airlines deal was found by Cheapflights users on 9/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2911:00 pm -
2 stops35h 15m
Fri 1/82:55 pm -
2 stops33h 16m
Deal found 9/24![United Airlines logo]()
$767
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/234:16 pm -
2 stops16h 49m
Thu 11/2612:59 pm -
2 stops26h 16m
Deal found 9/28![American Airlines logo]()
$783
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 29, 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 29, 2026.
This Delta deal was found by Cheapflights users on 9/28. 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 11/1210:40 pm -
1 stop10h 45m
Thu 11/191:40 pm -
1 stop11h 32m
Deal found 9/28![Delta logo]()
$598
This United Airlines deal was found by Cheapflights users on 9/27. 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 stops30h 23m
Deal found 9/27![United Airlines logo]()
$692
This American Airlines deal was found by Cheapflights users on 9/25. 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 stops16h 16m
Fri 1/88:25 am -
2 stops16h 47m
Deal found 9/25![American Airlines logo]()
$753
This United Airlines deal was found by Cheapflights users on 9/28. 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 11/64:10 pm -
2 stops21h 25m
Tue 11/105:45 pm -
2 stops21h 17m
Deal found 9/28![United Airlines logo]()
$728
This United Airlines deal was found by Cheapflights users on 9/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2911:00 pm -
2 stops35h 15m
Fri 1/82:55 pm -
2 stops33h 16m
Deal found 9/24![United Airlines logo]()
$767
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated September 29, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/92:41 pm -
2 stops18h 19m
Wed 10/148:00 am -
2 stops12h 31m
Deal found 9/28![American Airlines logo]()
$1,117
This Delta deal was found by Cheapflights users on 9/28. 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 10/202:37 pm -
2 stops43h 03m
Sat 10/241:05 pm -
1 stop10h 20m
Deal found 9/28![Delta logo]()
$1,003
This Delta deal was found by Cheapflights users on 9/28. 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 10/202:37 pm -
2 stops43h 03m
Sun 10/2512:55 pm -
2 stops23h 51m
Deal found 9/28![Delta logo]()
$1,232
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 29, 2026.
Round-trip from | $572 (American 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 September 29, 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
Quickest round-trip
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 11/12
10:40 pm-12:25 pm
1 stop10h 45m
George Town Owen Roberts Intl
Thu 11/19
1:40 pm-10:12 pm
1 stop11h 32m
$598
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-9:08 pm
2 stops30h 23m
$692
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 11/6
4:10 pm-4:35 pm
2 stops21h 25m
George Town Owen Roberts Intl
Tue 11/10
5:45 pm-12:02 pm
2 stops21h 17m
$728
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
7:19 pm-2:35 pm
2 stops16h 16m
George Town Owen Roberts Intl
Fri 1/8
8:25 am-10:12 pm
2 stops16h 47m
$753
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
11:00 pm-1:15 pm
2 stops35h 15m
George Town Owen Roberts Intl
Fri 1/8
2:55 pm-9:11 pm
2 stops33h 16m
$767
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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