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Cayman Islands

$587+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
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 July 24, 2026.

This Southwest deal was found by Cheapflights users on 7/21. 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 11/127:20 pm
SJC
-
GCM
2 stops14h 15m
Southwest
Tue 11/171:30 pm
GCM
-
SJC
2 stops21h 05m
Southwest
Deal found 7/21$587
This Southwest deal was found by Cheapflights users on 7/21. 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 11/127:30 pm
SJC
-
GCM
2 stops14h 05m
Southwest
Mon 11/161:30 pm
GCM
-
SJC
2 stops21h 05m
Southwest
Deal found 7/21$692
This American Airlines deal was found by Cheapflights users on 7/22. 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 8/1512:42 pm
SJC
-
GCM
2 stops22h 28m
American Airlines
Sat 8/2211:55 am
GCM
-
SJC
2 stops12h 37m
American Airlines
Deal found 7/22$716
This Delta deal was found by Cheapflights users on 7/22. 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 stop11h 20m
Delta
Thu 1/72:05 pm
GCM
-
SJC
1 stop9h 53m
Delta
Deal found 7/22$801
This Delta deal was found by Cheapflights users on 7/21. 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 11/128:05 pm
SJC
-
GCM
2 stops13h 20m
Delta
Tue 11/171:50 pm
GCM
-
SJC
1 stop12h 08m
Delta
Deal found 7/21$806
This United Airlines deal was found by Cheapflights users on 7/23. 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 12/74:00 pm
SJC
-
GCM
2 stops21h 30m
United Airlines
Thu 12/105:45 pm
GCM
-
SJC
2 stops30h 26m
United Airlines
Deal found 7/23$836
This Delta deal was found by Cheapflights users on 7/23. 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 stop11h 20m
Delta
Fri 1/82:05 pm
GCM
-
SJC
1 stop9h 53m
Delta
Deal found 7/23$854
This United Airlines deal was found by Cheapflights users on 7/20. 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 12/2910:55 pm
SJC
-
GCM
2 stops35h 20m
United Airlines
Fri 1/82:50 pm
GCM
-
SJC
2 stops25h 36m
United Airlines
Deal found 7/20$861
This American Airlines deal was found by Cheapflights users on 7/22. 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 stops13h 40m
American Airlines
Fri 1/83:40 pm
GCM
-
SJC
2 stops22h 17m
American Airlines
Deal found 7/22$866

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 24, 2026.

Round-trip from

$587
(Southwest)
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 July 24, 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

Tue 12/29

10:20 pm-12:40 pm

1 stop11h 20m

George Town Owen Roberts Intl

Fri 1/8

2:05 pm-8:58 pm

1 stop9h 53m

$801

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 11/12

10:20 pm-12:25 pm

1 stop11h 05m

George Town Owen Roberts Intl

Tue 11/17

1:50 pm-10:58 pm

1 stop12h 08m

$801

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 8/18

1:46 pm-11:39 am

2 stops19h 53m

George Town Owen Roberts Intl

Mon 8/24

1:04 pm-10:58 pm

1 stop11h 54m

$806

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 12/7

4:00 pm-4:30 pm

2 stops21h 30m

George Town Owen Roberts Intl

Thu 12/10

5:45 pm-9:11 pm

2 stops30h 26m

$836

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

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 $801, Delta can have you in Cayman Islands from San Jose, California in 11h 20m. Airlines will cover a distance of 2735 mi.

  • 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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