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Cayman Islands

$186+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Jul 30 — Aug 61
Thu 7/30
Thu 8/6
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 30, 2026.

This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:10 pm
SJC
-
GCM
2 stops17h 25m
Southwest
Thu 11/191:30 pm
GCM
-
SJC
2 stops21h 15m
Southwest
Deal found 6/28$544
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Mon 8/1712:03 pm
SJC
-
GCM
2 stops20h 57m
American Airlines
Sat 8/223:17 pm
GCM
-
SJC
1 stop9h 15m
American Airlines
Deal found 6/29$696
This American Airlines deal was found by Cheapflights users on 6/25. 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 8/97:14 pm
SJC
-
GCM
2 stops14h 13m
American Airlines
Sun 8/162:10 pm
GCM
-
SJC
2 stops22h 40m
American Airlines
Deal found 6/25$701
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Mon 8/311:47 am
SJC
-
GCM
1 stop23h 49m
American Airlines
Fri 8/712:30 pm
GCM
-
SJC
2 stops24h 20m
American Airlines
Deal found 6/25$711
This American Airlines deal was found by Cheapflights users on 6/28. 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 7/127:23 pm
SJC
-
GCM
2 stops18h 47m
American Airlines
Fri 7/1712:02 pm
GCM
-
SJC
2 stops12h 56m
American Airlines
Deal found 6/28$782
This Delta deal was found by Cheapflights users on 6/29. 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 12/2910:20 pm
SJC
-
GCM
1 stop11h 20m
Delta
Fri 1/82:05 pm
GCM
-
SJC
1 stop9h 53m
Delta
Deal found 6/29$801
This Delta deal was found by Cheapflights users on 6/25. 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 7/317:10 pm
SJC
-
GCM
2 stops14h 21m
Delta
Thu 8/61:04 pm
GCM
-
SJC
1 stop11h 54m
Delta
Deal found 6/25$806
This Delta deal was found by Cheapflights users on 6/25. 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 8/210:00 pm
SJC
-
GCM
1 stop11h 39m
Delta
Fri 8/71:04 pm
GCM
-
SJC
1 stop11h 54m
Delta
Deal found 6/25$841
This American Airlines deal was found by Cheapflights users on 6/30. 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 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 stops16h 33m
American Airlines
Fri 1/88:45 am
GCM
-
SJC
2 stops17h 04m
American Airlines
Deal found 6/30$846
This United Airlines deal was found by Cheapflights users on 6/25. 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 7/196:37 pm
SJC
-
GCM
2 stops15h 53m
United Airlines
Fri 7/311:35 pm
GCM
-
SJC
2 stops33h 35m
United Airlines
Deal found 6/25$851
This United Airlines deal was found by Cheapflights users on 6/25. 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 7/201:10 pm
SJC
-
GCM
1 stop21h 20m
United Airlines
Fri 7/311:35 pm
GCM
-
SJC
2 stops33h 35m
United Airlines
Deal found 6/25$858

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 30, 2026.

Round-trip from

$544
(Southwest)

One-way from

$186
(Southwest)
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 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

Price

Cheapest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 11/16

4:10 pm-12:35 pm

2 stops17h 25m

George Town Owen Roberts Intl

Thu 11/19

1:30 pm-7:45 am

2 stops21h 15m

$544

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 8/12

12:03 pm-1:10 pm

2 stops23h 07m

George Town Owen Roberts Intl

Wed 8/19

2:10 pm-10:50 am

2 stops22h 40m

$701
Quickest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 11/16

10:20 pm-12:25 pm

1 stop11h 05m

George Town Owen Roberts Intl

Thu 11/19

1:50 pm-10:58 pm

1 stop12h 08m

$801

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 8/12

2:59 pm-11:39 am

2 stops18h 40m

George Town Owen Roberts Intl

Wed 8/19

1:04 pm-9:41 pm

1 stop10h 37m

$806

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 7/23

2:32 pm-1:30 pm

2 stops44h 58m

George Town Owen Roberts Intl

Fri 7/31

1:35 pm-9:10 pm

2 stops33h 35m

$862

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 7/19

6:37 pm-12:30 pm

2 stops15h 53m

George Town Owen Roberts Intl

Tue 7/28

1:35 pm-5:35 pm

2 stops30h 00m

$977

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 8/9

10:20 pm-11:39 am

1 stop11h 19m

George Town Owen Roberts Intl

Sun 8/16

1:04 pm-10:58 pm

1 stop11h 54m

$1,071

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 7/22

10:00 pm-11:31 am

1 stop11h 31m

George Town Owen Roberts Intl

Wed 7/29

12:56 pm-10:49 pm

1 stop11h 53m

$1,095

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 12/21

10:20 pm-2:30 pm

1 stop13h 10m

George Town Owen Roberts Intl

Mon 12/28

3:50 pm-10:58 pm

1 stop10h 08m

$1,390

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 12/22

10:30 pm-1:45 pm

1 stop12h 15m

George Town Owen Roberts Intl

Mon 12/28

5:45 pm-9:11 pm

2 stops30h 26m

$1,490

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 13 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 $801, Southwest can have you in Cayman Islands from San Jose, California in 11h 05m. 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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