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Cayman Islands

$234+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap 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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$459
(Delta)

One-way from

$234
(American Airlines)
Provider with most accurate pricing for San Jose-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for San Jose-George Town Owen Roberts Intl flights.
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From San Jose to Cayman Islands
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One-way flight from San Jose to Cayman Islands
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Find 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 January 15, 2026.

This Delta deal was found by Cheapflights users on 1/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:35 pm
SJC
-
GCM
1 stop10h 54m
Delta
Tue 3/31:54 pm
GCM
-
SJC
2 stops21h 24m
Delta
Deal found 1/15$459
This Delta deal was found by Cheapflights users on 1/13. 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 2/1910:35 pm
SJC
-
GCM
1 stop10h 54m
Delta
Wed 2/251:54 pm
GCM
-
SJC
1 stop10h 24m
Delta
Deal found 1/13$530
This Delta deal was found by Cheapflights users on 1/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:20 pm
SJC
-
GCM
1 stop11h 20m
Delta
Fri 9/2512:55 pm
GCM
-
SJC
1 stop11h 46m
Delta
Deal found 1/14$573
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Mon 4/132:02 pm
SJC
-
GCM
2 stops18h 58m
American Airlines
Sun 4/192:10 pm
GCM
-
SJC
2 stops23h 56m
American Airlines
Deal found 1/14$583
This Delta deal was found by Cheapflights users on 1/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/133:45 pm
SJC
-
GCM
2 stops16h 15m
Delta
Fri 2/201:54 pm
GCM
-
SJC
1 stop10h 24m
Delta
Deal found 1/14$824
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Fri 2/137:15 pm
SJC
-
GCM
2 stops13h 08m
American Airlines
Fri 2/203:45 pm
GCM
-
SJC
2 stops21h 26m
American Airlines
Deal found 1/14$830
This Delta deal was found by Cheapflights users on 1/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:45 pm
SJC
-
GCM
1 stop10h 39m
Delta
Sun 4/1912:45 pm
GCM
-
SJC
1 stop10h 49m
Delta
Deal found 1/14$912

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 January 15, 2026.
Use the filters below to find and compare flights from San Jose to the Cayman Islands that are best for you.

Fly from

San Jose

Fly to

Cayman Islands

Route

Depart

Return

Price

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 2/22

10:35 pm-12:29 pm

1 stop10h 54m

George Town Owen Roberts Intl

Tue 3/3

1:54 pm-8:18 am

2 stops21h 24m

$459

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 2/19

10:35 pm-12:29 pm

1 stop10h 54m

George Town Owen Roberts Intl

Wed 2/25

1:54 pm-9:18 pm

1 stop10h 24m

$530

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/13

2:02 pm-11:00 am

2 stops18h 58m

George Town Owen Roberts Intl

Sun 4/19

2:10 pm-12:06 pm

2 stops23h 56m

$583

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 2/13

3:45 pm-11:00 am

2 stops16h 15m

George Town Owen Roberts Intl

Fri 2/20

1:54 pm-9:18 pm

1 stop10h 24m

$824

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 2/13

7:15 pm-11:23 am

2 stops13h 08m

George Town Owen Roberts Intl

Fri 2/20

3:45 pm-10:11 am

2 stops21h 26m

$830

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/13

10:45 pm-11:24 am

1 stop10h 39m

George Town Owen Roberts Intl

Sun 4/19

12:45 pm-9:34 pm

1 stop10h 49m

$912

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

1:00 pm-12:30 pm

1 stop21h 30m

George Town Owen Roberts Intl

Sat 6/27

4:45 pm-10:36 pm

2 stops31h 51m

$935

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 2/6

10:15 pm-2:45 pm

1 stop13h 30m

$234

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 2/10

2:32 pm-8:20 pm

2 stops26h 48m

$251

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/15

8:45 am-12:45 pm

2 stops26h 00m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 13 results
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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

What is the cheapest month to book a flight from San Jose, California to Cayman Islands?

Currently, February is the cheapest month in which you can book a flight from San Jose, California to Cayman Islands (average of $408). Flying from San Jose, California to Cayman Islands in August is currently the most expensive (average of $553). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 $459, Delta can have you in Cayman Islands from San Jose, California in 10h 54m. 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.

  • What is the cheapest month to book a flight from San Jose, California to Cayman Islands?

    Currently, February is the cheapest month in which you can book a flight from San Jose, California to Cayman Islands (average of $408). Flying from San Jose, California to Cayman Islands in August is currently the most expensive (average of $553). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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