$528+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Nov 1 — Nov 81
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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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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 2, 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 2, 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 American Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 12/162:58 pm -
2 stops17h 54m
Sun 12/203:51 pm -
1 stop10h 35m
Deal found 9/29![American Airlines logo]()
$644
This American Airlines deal was found by Cheapflights users on 9/29. 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 11/134:14 pm -
2 stops16h 01m
Fri 11/2012:59 pm -
2 stops13h 55m
Deal found 9/29![American Airlines logo]()
$690
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 Delta deal was found by Cheapflights users on 9/29. 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 11/1310:40 pm -
1 stop11h 03m
Fri 11/201:40 pm -
1 stop11h 32m
Deal found 9/29![Delta logo]()
$736
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 2, 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 2, 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 American Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 12/162:58 pm -
2 stops17h 54m
Sun 12/203:51 pm -
1 stop10h 35m
Deal found 9/29![American Airlines logo]()
$644
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 Delta deal was found by Cheapflights users on 9/29. 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 11/1310:40 pm -
1 stop11h 03m
Fri 11/201:40 pm -
1 stop11h 32m
Deal found 9/29![Delta logo]()
$736
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 11/62:14 pm -
1 stop20h 31m
Tue 11/105:45 pm -
2 stops21h 17m
Deal found 9/28![United Airlines logo]()
$744
This American Airlines deal was found by Cheapflights users on 10/1. 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 12/296:00 am -
2 stops10h 53m
Fri 1/84:07 pm -
2 stops22h 06m
Deal found 10/1![American Airlines logo]()
$753
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 2, 2026 and is based on user searches.
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 9/28. 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 American Airlines deal was found by Cheapflights users on 9/29. 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 11/134:14 pm -
2 stops16h 01m
Fri 11/2012:59 pm -
2 stops13h 55m
Deal found 9/29![American Airlines logo]()
$690
This Delta deal was found by Cheapflights users on 9/29. 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 11/1310:40 pm -
1 stop11h 03m
Fri 11/201:40 pm -
1 stop11h 32m
Deal found 9/29![Delta logo]()
$736
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
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/233:10 pm -
3 stops42h 00m
Thu 11/261:10 pm -
3 stops28h 05m
Deal found 9/28![Multiple Airlines logo]()
$861
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 2, 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 2, 2026.
This Delta deal was found by Cheapflights users on 9/30. 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 2/275:00 pm -
2 stops16h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$528
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 2, 2026.
Round-trip from | $572 (American Airlines) |
|---|---|
One-way from | $528 (Delta) |
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 2, 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
Sat 2/27
5:00 pm-12:40 pm
2 stops16h 40m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$528
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
Wed 12/16
2:58 pm-11:52 am
2 stops17h 54m
George Town Owen Roberts Intl
Sun 12/20
3:51 pm-11:26 pm
1 stop10h 35m
$644
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 11/13
10:40 pm-12:43 pm
1 stop11h 03m
George Town Owen Roberts Intl
Fri 11/20
1:40 pm-10:12 pm
1 stop11h 32m
$736
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 11/6
2:14 pm-1:45 pm
1 stop20h 31m
George Town Owen Roberts Intl
Tue 11/10
5:45 pm-12:02 pm
2 stops21h 17m
$744
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
6:00 am-7:53 pm
2 stops10h 53m
George Town Owen Roberts Intl
Fri 1/8
4:07 pm-11:13 am
2 stops22h 06m
$753
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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