$186+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Jul 31 — Aug 71
Round-trip
1 adult, Economy
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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 July 1, 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 July 1, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:10 pm
SJC
- GCM
2 stops17h 25m
Southwest
Thu 11/191:30 pm
GCM
- SJC
2 stops21h 15m
Southwest
Deal found 6/28![Southwest logo]()
$544
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Mon 8/1712:03 pm
SJC
- GCM
2 stops20h 57m
American Airlines
Sat 8/223:17 pm
GCM
- SJC
1 stop9h 15m
American Airlines
Deal found 6/29![American Airlines logo]()
$696
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Wed 8/1212:03 pm
SJC
- GCM
2 stops23h 07m
American Airlines
Wed 8/192:10 pm
GCM
- SJC
2 stops22h 40m
American Airlines
Deal found 6/28![American Airlines logo]()
$701
This American Airlines deal was found by Cheapflights users on 6/28. 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 7/127:23 pm
SJC
- GCM
2 stops18h 47m
American Airlines
Fri 7/1712:02 pm
GCM
- SJC
2 stops12h 56m
American Airlines
Deal found 6/28![American Airlines logo]()
$782
This Delta deal was found by Cheapflights users on 6/30. 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 12/2910:20 pm
SJC
- GCM
1 stop13h 10m
Delta
Fri 1/82:05 pm
GCM
- SJC
1 stop9h 53m
Delta
Deal found 6/30![Delta logo]()
$801
This Delta deal was found by Cheapflights users on 6/28. 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 8/122:59 pm
SJC
- GCM
2 stops18h 40m
Delta
Wed 8/191:04 pm
GCM
- SJC
1 stop10h 37m
Delta
Deal found 6/28![Delta logo]()
$806
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:17 pm
SJC
- GCM
2 stops16h 33m
American Airlines
Fri 1/88:45 am
GCM
- SJC
2 stops17h 04m
American Airlines
Deal found 6/30![American Airlines logo]()
$846
This Southwest deal was found by Cheapflights users on 6/29. 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 7/27:40 pm
SJC
- GCM
2 stops14h 15m
Southwest
Wed 7/812:50 pm
GCM
- SJC
2 stops11h 40m
Southwest
Deal found 6/29![Southwest logo]()
$932
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/27:23 pm
SJC
- GCM
2 stops18h 47m
American Airlines
Wed 7/82:41 pm
GCM
- SJC
1 stop10h 17m
American Airlines
Deal found 6/29![American Airlines logo]()
$1,001
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 July 1, 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 July 1, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:10 pm
SJC
- GCM
2 stops17h 25m
Southwest
Thu 11/191:30 pm
GCM
- SJC
2 stops21h 15m
Southwest
Deal found 6/28![Southwest logo]()
$544
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Mon 8/1712:03 pm
SJC
- GCM
2 stops20h 57m
American Airlines
Sat 8/223:17 pm
GCM
- SJC
1 stop9h 15m
American Airlines
Deal found 6/29![American Airlines logo]()
$696
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 11/1610:20 pm
SJC
- GCM
1 stop11h 05m
Delta
Thu 11/191:50 pm
GCM
- SJC
1 stop12h 08m
Delta
Deal found 6/28![Delta logo]()
$801
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Wed 8/1212:03 pm
SJC
- GCM
2 stops23h 07m
American Airlines
Wed 8/192:10 pm
GCM
- SJC
2 stops22h 40m
American Airlines
Deal found 6/28![American Airlines logo]()
$701
This Delta deal was found by Cheapflights users on 6/29. 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.
Mon 8/1710:20 pm
SJC
- GCM
1 stop11h 19m
Delta
Sat 8/221:04 pm
GCM
- SJC
1 stop10h 37m
Delta
Deal found 6/29![Delta logo]()
$801
This Delta deal was found by Cheapflights users on 6/28. 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 8/122:59 pm
SJC
- GCM
2 stops18h 40m
Delta
Wed 8/191:04 pm
GCM
- SJC
1 stop10h 37m
Delta
Deal found 6/28![Delta logo]()
$806
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Sun 8/167:14 pm
SJC
- GCM
2 stops14h 13m
American Airlines
Sat 8/222:10 pm
GCM
- SJC
2 stops22h 40m
American Airlines
Deal found 6/29![American Airlines logo]()
$1,596
This American Airlines deal was found by Cheapflights users on 6/28. 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 11/166:10 am
SJC
- GCM
2 stops11h 10m
American Airlines
Thu 11/199:00 am
GCM
- SJC
3 stops16h 16m
American Airlines
Deal found 6/28![American Airlines logo]()
$1,950
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated July 1, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated July 1, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/29. 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 7/27:40 pm
SJC
- GCM
2 stops14h 15m
Southwest
Wed 7/812:50 pm
GCM
- SJC
2 stops11h 40m
Southwest
Deal found 6/29![Southwest logo]()
$932
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/27:23 pm
SJC
- GCM
2 stops18h 47m
American Airlines
Wed 7/82:41 pm
GCM
- SJC
1 stop10h 17m
American Airlines
Deal found 6/29![American Airlines logo]()
$1,001
This Delta deal was found by Cheapflights users on 6/29. 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 7/210:00 pm
SJC
- GCM
1 stop11h 34m
Delta
Wed 7/812:56 pm
GCM
- SJC
1 stop11h 53m
Delta
Deal found 6/29![Delta logo]()
$1,960
This American Airlines deal was found by Cheapflights users on 6/28. 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 7/127:23 pm
SJC
- GCM
2 stops18h 47m
American Airlines
Fri 7/1712:02 pm
GCM
- SJC
2 stops12h 56m
American Airlines
Deal found 6/28![American Airlines logo]()
$782
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Wed 8/1212:03 pm
SJC
- GCM
2 stops23h 07m
American Airlines
Wed 8/192:10 pm
GCM
- SJC
2 stops22h 40m
American Airlines
Deal found 6/28![American Airlines logo]()
$701
This Delta deal was found by Cheapflights users on 6/28. 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 8/122:59 pm
SJC
- GCM
2 stops18h 40m
Delta
Wed 8/191:04 pm
GCM
- SJC
1 stop10h 37m
Delta
Deal found 6/28![Delta logo]()
$806
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Sun 8/167:14 pm
SJC
- GCM
2 stops14h 13m
American Airlines
Sat 8/222:10 pm
GCM
- SJC
2 stops22h 40m
American Airlines
Deal found 6/29![American Airlines logo]()
$1,596
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Mon 8/1712:03 pm
SJC
- GCM
2 stops20h 57m
American Airlines
Sat 8/223:17 pm
GCM
- SJC
1 stop9h 15m
American Airlines
Deal found 6/29![American Airlines logo]()
$696
This Delta deal was found by Cheapflights users on 6/29. 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.
Mon 8/1710:20 pm
SJC
- GCM
1 stop11h 19m
Delta
Sat 8/221:04 pm
GCM
- SJC
1 stop10h 37m
Delta
Deal found 6/29![Delta logo]()
$801
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 July 1, 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 July 1, 2026.
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:30 pm
SJC
- GCM
2 stops16h 05m
Southwest
Deal found 6/28![Southwest logo]()
$186
This Delta deal was found by Cheapflights users on 6/28. 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 11/1710:20 pm
SJC
- GCM
1 stop11h 05m
Delta
Deal found 6/28![Delta logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/172:22 pm
SJC
- GCM
3 stops44h 22m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$363
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 July 1, 2026.
Round-trip from | $544 (Southwest) |
|---|---|
One-way from | $186 (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 2,558,603 searches. Data last updated July 1, 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 - GCM
SJCGCM
San Jose
Mon 11/16
4:10 pm-12:35 pm
2 stops17h 25m
George Town Owen Roberts Intl
Thu 11/19
1:30 pm-7:45 am
2 stops21h 15m
$544
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Mon 8/17
12:03 pm-11:00 am
2 stops20h 57m
George Town Owen Roberts Intl
Sat 8/22
3:17 pm-10:32 pm
1 stop9h 15m
$696
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Wed 8/12
12:03 pm-1:10 pm
2 stops23h 07m
George Town Owen Roberts Intl
Wed 8/19
2:10 pm-10:50 am
2 stops22h 40m
$701
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Mon 11/16
10:20 pm-12:25 pm
1 stop11h 05m
George Town Owen Roberts Intl
Thu 11/19
1:50 pm-10:58 pm
1 stop12h 08m
$801
Quickest round-trip
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Mon 8/17
10:20 pm-11:39 am
1 stop11h 19m
George Town Owen Roberts Intl
Sat 8/22
1:04 pm-9:41 pm
1 stop10h 37m
$801
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Wed 8/12
2:59 pm-11:39 am
2 stops18h 40m
George Town Owen Roberts Intl
Wed 8/19
1:04 pm-9:41 pm
1 stop10h 37m
$806
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Sun 8/16
7:14 pm-11:27 am
2 stops14h 13m
George Town Owen Roberts Intl
Sat 8/22
2:10 pm-10:50 am
2 stops22h 40m
$1,596
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Mon 11/16
6:10 am-8:20 pm
2 stops11h 10m
George Town Owen Roberts Intl
Thu 11/19
9:00 am-10:16 pm
3 stops16h 16m
$1,950
Cheapest one-way
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Tue 11/17
5:30 pm-12:35 pm
2 stops16h 05m
$186
Quickest one-way
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Tue 11/17
10:20 pm-12:25 pm
1 stop11h 05m
$348
Showing 1-10 of 11 resultsSorted 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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