$562+ 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 5 — Oct 121
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
Cheapest
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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. 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 11/124:10 pm -
2 stops21h 20m
Mon 11/165:45 pm -
2 stops21h 17m
Deal found 9/2![United Airlines logo]()
$562
This American Airlines deal was found by Cheapflights users on 9/2. 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 11/144:14 pm -
2 stops16h 41m
Sat 11/215:22 pm -
1 stop9h 32m
Deal found 9/2![American Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 9/2. 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 11/1510:40 pm -
1 stop10h 45m
Sun 11/221:50 pm -
1 stop11h 22m
Deal found 9/2![Delta logo]()
$602
This Southwest deal was found by Cheapflights users on 9/2. 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.
Sat 11/144:10 pm -
2 stops17h 25m
Sat 11/214:10 pm -
2 stops18h 35m
Deal found 9/2![Southwest logo]()
$612
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Thu 10/12:36 pm -
2 stops18h 24m
Tue 10/68:00 am -
2 stops16h 08m
Deal found 9/1![American Airlines logo]()
$625
This Delta deal was found by Cheapflights users on 9/2. 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 11/1510:40 pm -
1 stop10h 45m
Sat 11/212:08 pm -
1 stop11h 04m
Deal found 9/2![Delta logo]()
$647
This United Airlines deal was found by Cheapflights users on 9/1. 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 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 9/1![United Airlines logo]()
$652
This Delta deal was found by Cheapflights users on 9/2. 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 11/146:20 am -
2 stops27h 05m
Fri 11/201:40 pm -
1 stop11h 32m
Deal found 9/2![Delta logo]()
$682
This United Airlines deal was found by Cheapflights users on 9/2. 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 11/154:10 pm -
2 stops21h 20m
Sat 11/215:10 pm -
2 stops23h 08m
Deal found 9/2![United Airlines logo]()
$702
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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. 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 11/124:10 pm -
2 stops21h 20m
Mon 11/165:45 pm -
2 stops21h 17m
Deal found 9/2![United Airlines logo]()
$562
This Delta deal was found by Cheapflights users on 9/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/85:05 pm -
2 stops18h 10m
Wed 1/202:05 pm -
1 stop9h 53m
Deal found 9/1![Delta logo]()
$562
This American Airlines deal was found by Cheapflights users on 9/4. 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 1/163:02 pm -
2 stops17h 43m
Sat 1/234:40 pm -
1 stop21h 30m
Deal found 9/4![American Airlines logo]()
$630
This United Airlines deal was found by Cheapflights users on 9/3. 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 9/3![United Airlines logo]()
$652
This Delta deal was found by Cheapflights users on 9/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/95:45 am -
2 stops27h 55m
Fri 1/152:05 pm -
1 stop9h 53m
Deal found 9/1![Delta logo]()
$652
This United Airlines deal was found by Cheapflights users on 9/2. 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 11/154:10 pm -
2 stops21h 20m
Sun 11/222:25 pm -
2 stops24h 37m
Deal found 9/2![United Airlines logo]()
$702
This Delta deal was found by Cheapflights users on 9/2. 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 11/124:33 pm -
2 stops16h 52m
Mon 11/161:40 pm -
1 stop11h 32m
Deal found 9/2![Delta logo]()
$752
This United Airlines deal was found by Cheapflights users on 9/3. 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 stops25h 31m
Deal found 9/3![United Airlines logo]()
$757
This Delta deal was found by Cheapflights users on 9/2. 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 10m
Fri 1/82:05 pm -
1 stop9h 53m
Deal found 9/2![Delta logo]()
$792
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated September 5, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Thu 10/12:36 pm -
2 stops18h 24m
Tue 10/68:00 am -
2 stops16h 08m
Deal found 9/1![American Airlines logo]()
$625
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 5, 2026.
Round-trip from | $532 (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 September 5, 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
4:10 pm-4:30 pm
2 stops21h 20m
George Town Owen Roberts Intl
Mon 11/16
5:45 pm-12:02 pm
2 stops21h 17m
$562
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 1/8
5:05 pm-2:15 pm
2 stops18h 10m
George Town Owen Roberts Intl
Wed 1/20
2:05 pm-8:58 pm
1 stop9h 53m
$562
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sat 1/16
3:02 pm-11:45 am
2 stops17h 43m
George Town Owen Roberts Intl
Sat 1/23
4:40 pm-11:10 am
1 stop21h 30m
$630
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 11/2
2:14 pm-4:30 pm
2 stops23h 16m
George Town Owen Roberts Intl
Thu 11/5
5:45 pm-10:59 pm
2 stops32h 14m
$652
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sat 1/9
5:45 am-12:40 pm
2 stops27h 55m
George Town Owen Roberts Intl
Fri 1/15
2:05 pm-8:58 pm
1 stop9h 53m
$652
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sun 11/15
4:10 pm-4:30 pm
2 stops21h 20m
George Town Owen Roberts Intl
Sun 11/22
2:25 pm-12:02 pm
2 stops24h 37m
$702
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 11/12
4:33 pm-12:25 pm
2 stops16h 52m
George Town Owen Roberts Intl
Mon 11/16
1:40 pm-10:12 pm
1 stop11h 32m
$752
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-1:26 pm
2 stops25h 31m
$757
Quickest round-trip
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
10:30 pm-12:40 pm
1 stop11h 10m
George Town Owen Roberts Intl
Fri 1/8
2:05 pm-8:58 pm
1 stop9h 53m
$792
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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