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Cayman Islands

$371+ 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 3/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This United Airlines deal was found by Cheapflights users on 3/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/283:45 pm
SJC
-
GCM
2 stops18h 45m
United Airlines
Tue 5/51:35 pm
GCM
-
SJC
2 stops25h 53m
United Airlines
Deal found 3/14$492
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Fri 5/152:02 pm
SJC
-
GCM
2 stops18h 53m
American Airlines
Wed 5/202:05 pm
GCM
-
SJC
2 stops23h 50m
American Airlines
Deal found 3/13$575
This American Airlines deal was found by Cheapflights users on 3/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:02 pm
SJC
-
GCM
2 stops19h 29m
American Airlines
Thu 5/712:00 pm
GCM
-
SJC
2 stops24h 10m
American Airlines
Deal found 3/16$604
This Delta deal was found by Cheapflights users on 3/14. 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.
Tue 4/2811:00 pm
SJC
-
GCM
1 stop11h 00m
Delta
Tue 5/51:25 pm
GCM
-
SJC
1 stop10h 20m
Delta
Deal found 3/14$644
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Fri 9/41:09 pm
SJC
-
GCM
2 stops20h 01m
American Airlines
Mon 9/712:25 pm
GCM
-
SJC
2 stops22h 53m
American Airlines
Deal found 3/13$668
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 7/262:35 pm
SJC
-
GCM
2 stops18h 26m
American Airlines
Sun 8/25:12 pm
GCM
-
SJC
2 stops22h 23m
American Airlines
Deal found 3/15$673
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 4/203:45 pm
SJC
-
GCM
2 stops18h 45m
United Airlines
Thu 4/231:50 pm
GCM
-
SJC
1 stop10h 51m
United Airlines
Deal found 3/15$690

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 March 17, 2026.

Round-trip from

$492
(United Airlines)

One-way from

$371
(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 March 17, 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 4/28

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Tue 5/5

1:35 pm-1:28 pm

2 stops25h 53m

$492

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 9/4

2:36 pm-11:25 am

2 stops18h 49m

George Town Owen Roberts Intl

Mon 9/7

12:25 pm-9:18 am

2 stops22h 53m

$668

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 7/26

12:39 pm-11:01 am

2 stops20h 22m

George Town Owen Roberts Intl

Sun 8/2

5:12 pm-1:35 pm

2 stops22h 23m

$673

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 5/15

2:02 pm-2:13 pm

1 stop22h 11m

George Town Owen Roberts Intl

Wed 5/20

2:05 pm-11:55 am

2 stops23h 50m

$676
Quickest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/20

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-10:41 pm

1 stop10h 51m

$690
Cheapest one-way

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 3/27

9:10 pm-10:25 am

2 stops11h 15m

$371

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 3/26

9:10 pm-11:45 am

2 stops12h 35m

$371

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 3/27

7:02 pm-12:57 pm

3 stops39h 55m

$428

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/6

3:45 pm-12:45 pm

2 stops43h 00m

$835
Quickest one-way

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/6

10:50 pm-11:47 am

1 stop10h 57m

$1,864

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

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

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 $405). Flying from San Jose, California to Cayman Islands in August is currently the most expensive (average of $545). 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 $644, United Airlines can have you in Cayman Islands from San Jose, California in 11h. 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.

  • 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 $405). Flying from San Jose, California to Cayman Islands in August is currently the most expensive (average of $545). 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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