$286+ Cheap flights from San Jose, CA (SJC) to the Cayman Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Oct 2 — Oct 91
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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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
One-way
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 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 September 2, 2026.
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 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 Southwest deal was found by Cheapflights users on 8/29. 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 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 8/29![Southwest logo]()
$682
This American Airlines deal was found by Cheapflights users on 8/29. 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 11/132:50 pm -
1 stop20h 40m
Mon 11/163:45 pm -
2 stops22h 21m
Deal found 8/29![American Airlines logo]()
$743
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.
Tue 12/297:19 pm -
2 stops16h 06m
Fri 1/88:21 am -
2 stops17h 21m
Deal found 9/1![American Airlines logo]()
$787
This Delta deal was found by Cheapflights users on 8/30. 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.
Tue 12/2910:30 pm -
1 stop11h 10m
Fri 1/82:05 pm -
1 stop9h 53m
Deal found 8/30![Delta logo]()
$792
This Delta deal was found by Cheapflights users on 8/29. 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.
Thu 11/1210:40 pm -
1 stop10h 45m
Mon 11/161:40 pm -
1 stop11h 32m
Deal found 8/29![Delta logo]()
$837
This American Airlines deal was found by Cheapflights users on 8/31. 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 12/197:19 pm -
2 stops13h 47m
Sat 12/268:30 am -
2 stops17h 56m
Deal found 8/31![American Airlines logo]()
$1,226
This Gotogate deal was found by Cheapflights users on 8/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/192:51 pm -
2 stops21h 54m
Sat 12/264:00 pm -
1 stop21h 23m
Deal found 8/31![Multiple Airlines logo]()
$1,243
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 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 September 2, 2026.
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 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 9/1. 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.
Tue 12/2910:30 pm -
1 stop11h 10m
Fri 1/82:05 pm -
1 stop9h 53m
Deal found 9/1![Delta logo]()
$792
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.
Tue 12/297:19 pm -
2 stops16h 06m
Fri 1/88:21 am -
2 stops17h 21m
Deal found 9/1![American Airlines logo]()
$787
This Delta deal was found by Cheapflights users on 8/29. 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.
Thu 11/127:25 pm -
2 stops14h 00m
Mon 11/161:40 pm -
1 stop11h 32m
Deal found 8/29![Delta logo]()
$797
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated September 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:10 pm -
2 stops44h 15m
Sat 9/191:35 pm -
2 stops24h 11m
Deal found 8/29![United Airlines logo]()
$2,525
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:10 pm -
2 stops20h 15m
Sat 9/191:35 pm -
2 stops24h 11m
Deal found 8/29![United Airlines logo]()
$2,454
This Delta deal was found by Cheapflights users on 8/29. 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.
Sun 9/136:19 pm -
2 stops15h 21m
Thu 9/171:00 pm -
2 stops12h 40m
Deal found 8/29![Delta logo]()
$3,066
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
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 September 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 September 2, 2026.
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 9/186:19 pm -
2 stops15h 21m
Deal found 8/28![Delta logo]()
$286
This American Airlines deal was found by Cheapflights users on 8/29. 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.
Thu 9/1712:48 pm -
2 stops20h 39m
Deal found 8/29![American Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 8/28. 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.
Sun 9/134:24 pm -
2 stops17h 16m
Deal found 8/28![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 8/28. 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.
Wed 9/166:00 am -
2 stops27h 40m
Deal found 8/28![Delta logo]()
$337
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Tue 9/1512:02 pm -
2 stops21h 25m
Deal found 8/28![American Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/142:48 pm -
2 stops42h 39m
Deal found 8/28![American Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 8/29. 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.
Thu 9/1710:45 pm -
1 stop10h 55m
Deal found 8/29![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 9/1112:51 pm -
1 stop20h 49m
Deal found 8/28![Delta logo]()
$567
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/116:00 am -
2 stops26h 55m
Deal found 8/28![American Airlines logo]()
$787
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sun 9/136:00 am -
2 stops27h 27m
Deal found 8/28![American Airlines logo]()
$841
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 2, 2026.
Round-trip from | $652 (United Airlines) |
|---|---|
One-way from | $286 (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 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
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 10/1
2:36 pm-11:00 am
2 stops18h 24m
George Town Owen Roberts Intl
Tue 10/6
8:00 am-10:08 pm
2 stops16h 08m
$625
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
Tue 12/29
7:19 pm-2:25 pm
2 stops16h 06m
George Town Owen Roberts Intl
Fri 1/8
8:21 am-10:42 pm
2 stops17h 21m
$787
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
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 11/12
7:25 pm-12:25 pm
2 stops14h 00m
George Town Owen Roberts Intl
Mon 11/16
1:40 pm-10:12 pm
1 stop11h 32m
$797
Cheapest one-way
Quickest one-way
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 9/18
10:50 pm-11:40 am
1 stop10h 50m
$286
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sun 9/13
4:24 pm-11:40 am
2 stops17h 16m
$331
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Sat 9/12
8:41 pm-11:40 am
2 stops12h 59m
$331
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 9/17
10:45 pm-11:40 am
1 stop10h 55m
$503
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 9/18
4:00 pm-4:10 pm
3 stops70h 10m
$3,961
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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