$236+ 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Nov 29 — Dec 61
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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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 30, 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 30, 2026.
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:30 pm -
1 stop11h 13m
Fri 12/181:59 pm -
1 stop11h 14m
Deal found 10/27![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/144:15 pm -
2 stops17h 20m
Mon 12/211:30 pm -
2 stops13h 25m
Deal found 10/30![Southwest logo]()
$700
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Wed 12/3011:00 pm -
1 stop11h 45m
Thu 1/72:55 pm -
1 stop24h 14m
Deal found 10/27![United Airlines logo]()
$704
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 12/114:10 pm -
2 stops20h 50m
Fri 12/185:10 pm -
2 stops23h 14m
Deal found 10/27![United Airlines logo]()
$722
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/295:30 pm -
2 stops18h 06m
Fri 1/82:39 pm -
1 stop10h 33m
Deal found 10/29![Delta logo]()
$733
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:48 pm -
3 stops21h 17m
Mon 12/2112:40 pm -
3 stops28h 50m
Deal found 10/30![Multiple Airlines logo]()
$740
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 12/2911:00 pm -
2 stops14h 00m
Fri 1/82:25 pm -
2 stops48h 44m
Deal found 10/28![United Airlines logo]()
$741
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 12/2911:00 pm -
1 stop11h 45m
Thu 1/72:55 pm -
1 stop24h 14m
Deal found 10/27![United Airlines logo]()
$748
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:40 pm -
3 stops22h 25m
Fri 12/1811:25 am -
3 stops30h 05m
Deal found 10/27![Multiple Airlines logo]()
$757
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Sun 12/134:10 pm -
2 stops21h 20m
Sun 12/205:45 pm -
2 stops32h 00m
Deal found 10/29![United Airlines logo]()
$761
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 30, 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 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/29. 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 2/267:11 pm -
2 stops12h 39m
Mon 3/89:15 am -
2 stops16h 29m
Deal found 10/29![American Airlines logo]()
$631
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:30 pm -
1 stop11h 13m
Fri 12/181:59 pm -
1 stop11h 14m
Deal found 10/27![Delta logo]()
$670
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 12/114:10 pm -
2 stops20h 50m
Fri 12/182:55 pm -
1 stop10h 50m
Deal found 10/27![United Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/144:15 pm -
2 stops17h 20m
Mon 12/211:30 pm -
2 stops13h 25m
Deal found 10/30![Southwest logo]()
$700
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/295:30 pm -
2 stops18h 06m
Fri 1/82:39 pm -
1 stop10h 33m
Deal found 10/29![Delta logo]()
$733
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 12/2911:00 pm -
2 stops14h 00m
Fri 1/82:25 pm -
2 stops48h 44m
Deal found 10/28![United Airlines logo]()
$741
Last-minute flights from San Jose to Cayman IslandsDiscover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Cayman Islands. Data last updated October 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 11/32:14 pm -
2 stops23h 16m
Thu 11/55:45 pm -
2 stops32h 14m
Deal found 10/28![United Airlines logo]()
$954
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Sat 11/72:14 pm -
2 stops23h 16m
Wed 11/115:45 pm -
2 stops21h 17m
Deal found 10/27![United Airlines logo]()
$818
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:13 pm -
2 stops26h 02m
Wed 11/111:10 pm -
3 stops30h 59m
Deal found 10/27![Multiple Airlines logo]()
$1,205
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/188:45 am -
2 stops28h 45m
Thu 11/265:45 pm -
2 stops30h 23m
Deal found 10/28![United Airlines logo]()
$904
This Delta deal was found by Cheapflights users on 10/28. 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 11/181:00 pm -
1 stop20h 25m
Thu 11/261:50 pm -
2 stops22h 18m
Deal found 10/28![Delta logo]()
$1,215
This Delta deal was found by Cheapflights users on 10/28. 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 11/1910:40 pm -
1 stop10h 45m
Fri 11/271:50 pm -
1 stop11h 22m
Deal found 10/28![Delta logo]()
$2,532
This Delta deal was found by Cheapflights users on 10/28. 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 11/1910:40 pm -
1 stop10h 45m
Sun 11/291:37 pm -
1 stop11h 35m
Deal found 10/28![Delta logo]()
$2,632
This Delta deal was found by Cheapflights users on 10/28. 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 11/2010:40 pm -
1 stop11h 03m
Fri 11/271:50 pm -
1 stop11h 22m
Deal found 10/28![Delta logo]()
$2,954
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/212:14 pm -
2 stops20h 01m
Fri 11/275:45 pm -
2 stops30h 23m
Deal found 10/28![United Airlines logo]()
$1,597
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 30, 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 30, 2026.
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:56 pm -
2 stops12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 10/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:50 pm -
2 stops15h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:52 pm -
3 stops45h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 10/29. 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 1/111:00 pm -
1 stop11h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![United Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 12/38:45 am -
2 stops28h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:05 pm -
1 stop20h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Delta logo]()
$542
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:30 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Delta logo]()
$680
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/274:16 pm -
2 stops19h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$911
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
3 stops25h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$913
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 30, 2026.
Round-trip from | $631 (American Airlines) |
|---|---|
One-way from | $236 (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 30, 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
Tue 12/1
8:56 pm-12:25 pm
2 stops12h 29m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$236
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Wed 12/2
5:50 pm-12:35 pm
2 stops15h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$239
Quickest round-trip
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 1/1
11:00 pm-1:45 pm
1 stop11h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$347
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Thu 12/3
8:45 am-4:30 pm
2 stops28h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$349
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Wed 12/2
1:05 pm-12:25 pm
1 stop20h 20m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$542
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 2/26
7:11 pm-10:50 am
2 stops12h 39m
George Town Owen Roberts Intl
Mon 3/8
9:15 am-10:44 pm
2 stops16h 29m
$631
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 12/11
10:30 pm-12:43 pm
1 stop11h 13m
George Town Owen Roberts Intl
Fri 12/18
1:59 pm-10:13 pm
1 stop11h 14m
$670
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Fri 12/11
4:10 pm-4:00 pm
2 stops20h 50m
George Town Owen Roberts Intl
Fri 12/18
2:55 pm-10:45 pm
1 stop10h 50m
$670
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Mon 12/14
4:15 pm-12:35 pm
2 stops17h 20m
George Town Owen Roberts Intl
Mon 12/21
1:30 pm-11:55 pm
2 stops13h 25m
$700
San JoseGeorge Town
SJC San Jose - GCM George Town Owen Roberts Intl
SJCGCM
San Jose
Tue 12/29
5:30 pm-2:36 pm
2 stops18h 06m
George Town Owen Roberts Intl
Fri 1/8
2:39 pm-10:12 pm
1 stop10h 33m
$733
Showing 1-10 of 15 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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