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Cayman Islands

$288+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Jul 18 — Jul 251
Sat 7/18
Sat 7/25
1 adult, Economy
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Cheap flight deals from San Jose to Cayman Islands

Cheapest flights from San Jose to Cayman Islands
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 18, 2026.

This American Airlines deal was found by Cheapflights users on 6/15. 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 7/97:23 pm
SJC
-
GCM
2 stops13h 37m
American Airlines
Wed 7/1512:02 pm
GCM
-
SJC
2 stops12h 39m
American Airlines
Deal found 6/15$674
This Southwest deal was found by Cheapflights users on 6/17. 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 12/297:30 pm
SJC
-
GCM
2 stops14h 05m
Southwest
Fri 1/81:50 pm
GCM
-
SJC
2 stops21h 05m
Southwest
Deal found 6/17$682
This Southwest deal was found by Cheapflights users on 6/14. 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 7/147:35 pm
SJC
-
GCM
2 stops14h 20m
Southwest
Mon 7/2012:50 pm
GCM
-
SJC
2 stops11h 45m
Southwest
Deal found 6/14$684
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/2912:39 pm
SJC
-
GCM
2 stops20h 21m
American Airlines
Fri 8/712:30 pm
GCM
-
SJC
2 stops24h 20m
American Airlines
Deal found 6/15$691
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/1411:47 am
SJC
-
GCM
1 stop23h 49m
American Airlines
Mon 7/205:10 pm
GCM
-
SJC
2 stops19h 39m
American Airlines
Deal found 6/14$701
This Delta deal was found by Cheapflights users on 6/16. 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 10/157:00 pm
SJC
-
GCM
2 stops14h 40m
Delta
Sun 10/2512:55 pm
GCM
-
SJC
1 stop12h 03m
Delta
Deal found 6/16$729
This Delta deal was found by Cheapflights users on 6/17. 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 6/17$791

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 18, 2026.

Round-trip from

$674
(American Airlines)

One-way from

$288
(Delta)
From San Jose to Cayman Islands
Search Deals
One-way flight from San Jose to Cayman Islands
Search Deals

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 18, 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

Price

Cheapest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 7/14

7:35 pm-11:55 am

2 stops14h 20m

George Town Owen Roberts Intl

Mon 7/20

12:50 pm-10:35 pm

2 stops11h 45m

$684
Quickest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 7/9

7:23 pm-11:25 am

2 stops14h 02m

George Town Owen Roberts Intl

Wed 7/15

2:41 pm-10:58 pm

1 stop10h 17m

$686

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 10/15

2:36 pm-10:45 am

2 stops18h 09m

George Town Owen Roberts Intl

Sun 10/25

3:30 pm-10:53 am

2 stops21h 23m

$691

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 7/14

11:47 am-1:36 pm

1 stop23h 49m

George Town Owen Roberts Intl

Mon 7/20

5:10 pm-10:49 am

2 stops19h 39m

$701

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 10/15

7:00 pm-11:40 am

2 stops14h 40m

George Town Owen Roberts Intl

Sun 10/25

12:55 pm-10:58 pm

1 stop12h 03m

$729

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 7/17

6:37 pm-3:35 pm

2 stops18h 58m

George Town Owen Roberts Intl

Sat 8/1

4:45 pm-12:03 pm

1 stop21h 18m

$825

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 7/18

4:00 pm-12:30 pm

2 stops42h 30m

George Town Owen Roberts Intl

Sat 8/1

4:45 pm-1:25 pm

2 stops22h 40m

$1,041

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 7/18

6:35 am-11:31 am

1 stop26h 56m

George Town Owen Roberts Intl

Sat 8/1

12:56 pm-9:41 pm

1 stop10h 45m

$1,465
Cheapest one-way

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 7/16

1:15 pm-11:31 am

2 stops20h 16m

$288

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 7/17

12:39 pm-10:55 am

2 stops20h 16m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 11 resultsSorted by cheapest first
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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.
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
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Jose to Cayman Islands?

    For a flight from San Jose to Cayman Islands, you will be flying from San Jose. San Jose (SJC) is just 2.9 mi from the center of the city.

  • How long is the flight from San Jose, California to Cayman Islands?

    For as low as $684, Southwest can have you in Cayman Islands from San Jose, California in 12h 15m. Airlines will cover a distance of 2735 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from San Jose to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on San Jose to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Cayman Islands.

  • Can I find deals for business class flights from San Jose to Cayman Islands?

    Yes. Cheapflights offers flight deals from San Jose to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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