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Cayman Islands

$307+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
May 16 — May 231
Sat 5/16
Sat 5/23
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 April 16, 2026.

This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:40 pm
SJC
-
GCM
2 stops12h 30m
Southwest
Wed 5/201:05 pm
GCM
-
SJC
2 stops11h 55m
Southwest
Deal found 4/15$534
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:19 pm
SJC
-
GCM
2 stops16h 11m
United Airlines
Wed 5/201:35 pm
GCM
-
SJC
1 stop24h 28m
United Airlines
Deal found 4/15$653
This Delta deal was found by Cheapflights users on 4/13. 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 5/282:49 pm
SJC
-
GCM
2 stops19h 05m
Delta
Thu 6/41:19 pm
GCM
-
SJC
1 stop11h 36m
Delta
Deal found 4/13$682
This American Airlines deal was found by Cheapflights users on 4/13. 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 5/2811:48 am
SJC
-
GCM
1 stop23h 51m
American Airlines
Thu 6/42:42 pm
GCM
-
SJC
1 stop10h 31m
American Airlines
Deal found 4/13$692
This United Airlines deal was found by Cheapflights users on 4/12. 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 5/42:46 pm
SJC
-
GCM
2 stops19h 44m
United Airlines
Thu 5/71:35 pm
GCM
-
SJC
1 stop24h 25m
United Airlines
Deal found 4/12$747
This United Airlines deal was found by Cheapflights users on 4/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:37 pm
SJC
-
GCM
2 stops42h 58m
United Airlines
Sat 6/274:45 pm
GCM
-
SJC
2 stops22h 40m
United Airlines
Deal found 4/16$827

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 April 16, 2026.

Round-trip from

$534
(Southwest)

One-way from

$307
(United Airlines)
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 April 16, 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
Quickest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 5/28

2:49 pm-11:54 am

2 stops19h 05m

George Town Owen Roberts Intl

Thu 6/4

1:19 pm-10:55 pm

1 stop11h 36m

$682

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 5/4

2:46 pm-12:30 pm

2 stops19h 44m

George Town Owen Roberts Intl

Thu 5/7

1:35 pm-12:00 pm

1 stop24h 25m

$747

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

6:37 pm-3:35 pm

2 stops42h 58m

George Town Owen Roberts Intl

Sat 6/27

4:45 pm-9:09 pm

2 stops30h 24m

$827
Cheapest one-way
Quickest one-way

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 8/8

2:45 pm-12:30 pm

2 stops19h 45m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

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.
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 $534, Southwest can have you in Cayman Islands from San Jose, California in 12h 30m. 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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