$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 6/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Jul 2 — Jul 91
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 June 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 June 2, 2026.
This Delta deal was found by Cheapflights users on 5/29. 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 9/2010:10 pm
SJC
- GCM
1 stop11h 30m
Delta
Sat 9/2612:55 pm
GCM
- SJC
1 stop10h 54m
Delta
Deal found 5/29![Delta logo]()
$627
This American Airlines deal was found by Cheapflights users on 5/29. 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 6/192:35 pm
SJC
- GCM
1 stop17h 47m
American Airlines
Mon 6/295:12 pm
GCM
- SJC
2 stops20h 53m
American Airlines
Deal found 5/29![American Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 7/12:35 pm
SJC
- GCM
2 stops18h 50m
American Airlines
Tue 7/75:10 pm
GCM
- SJC
2 stops19h 39m
American Airlines
Deal found 6/2![American Airlines logo]()
$687
This American Airlines deal was found by Cheapflights users on 5/28. 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 6/2112:38 pm
SJC
- GCM
2 stops20h 23m
American Airlines
Sun 6/285:12 pm
GCM
- SJC
2 stops22h 29m
American Airlines
Deal found 5/28![American Airlines logo]()
$699
This Faresmojo deal was found by Cheapflights users on 5/28. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2110:00 pm
SJC
- GCM
1 stop11h 34m
JetBlue
Sun 6/2812:59 pm
GCM
- SJC
1 stop11h 58m
JetBlue
Deal found 5/28![JetBlue logo]()
$708
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Thu 6/1812:38 pm
SJC
- GCM
2 stops20h 23m
American Airlines
Sat 6/273:35 pm
GCM
- SJC
1 stop9h 37m
American Airlines
Deal found 6/2![American Airlines logo]()
$727
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 June 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 June 2, 2026.
This Delta deal was found by Cheapflights users on 5/29. 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 9/2010:10 pm
SJC
- GCM
1 stop11h 30m
Delta
Sat 9/2612:55 pm
GCM
- SJC
1 stop10h 54m
Delta
Deal found 5/29![Delta logo]()
$627
This American Airlines deal was found by Cheapflights users on 5/29. 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 9/207:08 pm
SJC
- GCM
2 stops13h 52m
American Airlines
Sat 9/2611:55 am
GCM
- SJC
2 stops24h 58m
American Airlines
Deal found 5/29![American Airlines logo]()
$632
This Faresmojo deal was found by Cheapflights users on 5/28. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2110:00 pm
SJC
- GCM
1 stop11h 34m
JetBlue
Sun 6/2812:59 pm
GCM
- SJC
1 stop11h 58m
JetBlue
Deal found 5/28![JetBlue logo]()
$708
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Fri 6/197:24 pm
SJC
- GCM
2 stops17h 43m
American Airlines
Mon 6/295:12 pm
GCM
- SJC
2 stops20h 53m
American Airlines
Deal found 6/1![American Airlines logo]()
$727
This American Airlines deal was found by Cheapflights users on 6/1. 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 6/182:35 pm
SJC
- GCM
2 stops18h 26m
American Airlines
Sat 6/273:35 pm
GCM
- SJC
1 stop9h 37m
American Airlines
Deal found 6/1![American Airlines logo]()
$727
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 7/12:35 pm
SJC
- GCM
2 stops18h 26m
American Airlines
Tue 7/72:41 pm
GCM
- SJC
1 stop10h 17m
American Airlines
Deal found 6/2![American Airlines logo]()
$814
This Delta deal was found by Cheapflights users on 6/1. 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.
Thu 6/1810:00 pm
SJC
- GCM
1 stop11h 34m
Delta
Sat 6/2712:59 pm
GCM
- SJC
1 stop10h 43m
Delta
Deal found 6/1![Delta logo]()
$1,091
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated June 2, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated June 2, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/28. 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 6/310:00 pm
SJC
- GCM
1 stop11h 54m
Delta
Mon 6/812:59 pm
GCM
- SJC
1 stop11h 58m
Delta
Deal found 5/28![Delta logo]()
$887
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Thu 6/1812:38 pm
SJC
- GCM
2 stops20h 23m
American Airlines
Sat 6/273:35 pm
GCM
- SJC
1 stop9h 37m
American Airlines
Deal found 6/2![American Airlines logo]()
$727
This American Airlines deal was found by Cheapflights users on 5/29. 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 6/192:35 pm
SJC
- GCM
1 stop17h 47m
American Airlines
Mon 6/295:12 pm
GCM
- SJC
2 stops20h 53m
American Airlines
Deal found 5/29![American Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 5/28. 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 6/2112:38 pm
SJC
- GCM
2 stops20h 23m
American Airlines
Sun 6/285:12 pm
GCM
- SJC
2 stops22h 29m
American Airlines
Deal found 5/28![American Airlines logo]()
$699
This Faresmojo deal was found by Cheapflights users on 5/28. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2110:00 pm
SJC
- GCM
1 stop11h 34m
JetBlue
Sun 6/2812:59 pm
GCM
- SJC
1 stop11h 58m
JetBlue
Deal found 5/28![JetBlue logo]()
$708
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 7/12:35 pm
SJC
- GCM
2 stops18h 50m
American Airlines
Tue 7/75:10 pm
GCM
- SJC
2 stops19h 39m
American Airlines
Deal found 6/2![American Airlines logo]()
$687
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 June 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 June 2, 2026.
This Southwest deal was found by Cheapflights users on 6/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:45 pm
SJC
- GCM
2 stops14h 10m
Southwest
Deal found 6/1![Southwest logo]()
$286
This Delta deal was found by Cheapflights users on 6/1. 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.
Thu 6/256:00 am
SJC
- GCM
2 stops27h 34m
Delta
Deal found 6/1![Delta logo]()
$292
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Sat 6/2711:49 am
SJC
- GCM
1 stop23h 46m
American Airlines
Deal found 6/1![American Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:35 pm
SJC
- GCM
2 stops14h 35m
Southwest
Deal found 6/1![Southwest logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/1. 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 6/2312:40 pm
SJC
- GCM
2 stops20h 21m
American Airlines
Deal found 6/1![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Wed 6/246:01 am
SJC
- GCM
2 stops27h 29m
American Airlines
Deal found 6/1![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 6/1. 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.
Sun 6/286:01 am
SJC
- GCM
1 stop29h 34m
American Airlines
Deal found 6/1![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 6/1. 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 6/2310:00 pm
SJC
- GCM
1 stop11h 34m
Delta
Deal found 6/1![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 6/1. 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 9/186:10 pm
SJC
- GCM
2 stops15h 30m
Delta
Deal found 6/1![Delta logo]()
$493
This Mytrip deal was found by Cheapflights users on 6/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:59 pm
SJC
- GCM
3 stops18h 26m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$558
This Mytrip deal was found by Cheapflights users on 6/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:59 pm
SJC
- GCM
3 stops19h 46m
WestJet
Deal found 6/1![WestJet logo]()
$577
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 June 2, 2026.
Round-trip from | $627 (Delta) |
|---|---|
One-way from | $286 (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 June 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 - GCM
SJCGCM
San Jose
Sun 9/20
10:10 pm-11:40 am
1 stop11h 30m
George Town Owen Roberts Intl
Sat 9/26
12:55 pm-9:49 pm
1 stop10h 54m
$627
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Sun 9/20
7:08 pm-11:00 am
2 stops13h 52m
George Town Owen Roberts Intl
Sat 9/26
11:55 am-10:53 am
2 stops24h 58m
$632
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Sun 6/21
10:00 pm-11:34 am
1 stop11h 34m
George Town Owen Roberts Intl
Sun 6/28
12:59 pm-10:57 pm
1 stop11h 58m
$708
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Fri 6/19
7:24 pm-3:07 pm
2 stops17h 43m
George Town Owen Roberts Intl
Mon 6/29
5:12 pm-12:05 pm
2 stops20h 53m
$727
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Thu 6/18
2:35 pm-11:01 am
2 stops18h 26m
George Town Owen Roberts Intl
Sat 6/27
3:35 pm-11:12 pm
1 stop9h 37m
$727
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Wed 7/1
2:35 pm-11:01 am
2 stops18h 26m
George Town Owen Roberts Intl
Tue 7/7
2:41 pm-10:58 pm
1 stop10h 17m
$814
Quickest round-trip
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Thu 6/18
10:00 pm-11:34 am
1 stop11h 34m
George Town Owen Roberts Intl
Sat 6/27
12:59 pm-9:42 pm
1 stop10h 43m
$1,091
Cheapest one-way
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Thu 6/25
6:00 am-11:34 am
2 stops27h 34m
$292
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Fri 6/26
7:35 pm-12:10 pm
2 stops14h 35m
$331
San JoseGeorge Town
SJC - GCM
SJCGCM
San Jose
Mon 6/29
7:24 pm-11:30 am
2 stops14h 06m
$346
Showing 1-10 of 13 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.
Related info for your journey
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