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Cayman Islands

$329+ 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Mar 3 — Mar 101
Tue 3/3
Tue 3/10
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 February 1, 2026.

This United Airlines deal was found by Cheapflights users on 1/31. 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 3/173:49 pm
SJC
-
GCM
2 stops18h 26m
United Airlines
Tue 3/241:50 pm
GCM
-
SJC
1 stop11h 09m
United Airlines
Deal found 1/31$573
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/172:26 pm
SJC
-
GCM
1 stop21h 59m
American Airlines
Tue 3/243:30 pm
GCM
-
SJC
1 stop20h 46m
American Airlines
Deal found 1/31$599
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1610:55 pm
SJC
-
GCM
1 stop11h 50m
United Airlines
Mon 3/234:45 pm
GCM
-
SJC
2 stops30h 31m
United Airlines
Deal found 1/30$688
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/18:50 am
SJC
-
GCM
2 stops25h 55m
United Airlines
Wed 3/42:25 pm
GCM
-
SJC
2 stops26h 16m
United Airlines
Deal found 1/29$839
This United Airlines deal was found by Cheapflights users on 1/30. 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 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 stops40h 53m
United Airlines
Sat 6/274:15 pm
GCM
-
SJC
2 stops23h 09m
United Airlines
Deal found 1/30$877
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Thu 6/182:36 pm
SJC
-
GCM
2 stops18h 24m
American Airlines
Sat 6/272:40 pm
GCM
-
SJC
1 stop9h 31m
American Airlines
Deal found 1/30$1,073
This Delta deal was found by Cheapflights users on 1/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1810:20 pm
SJC
-
GCM
1 stop11h 05m
Delta
Sat 6/271:10 pm
GCM
-
SJC
1 stop11h 43m
Delta
Deal found 1/30$1,151
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:32 pm
SJC
-
GCM
2 stops19h 58m
United Airlines
Fri 8/71:35 pm
GCM
-
SJC
2 stops25h 49m
United Airlines
Deal found 1/30$7,556

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 February 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$573
(United Airlines)

One-way from

$329
(United 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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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 February 1, 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

Tue 3/17

3:49 pm-12:15 pm

2 stops18h 26m

George Town Owen Roberts Intl

Tue 3/24

4:45 pm-1:41 pm

2 stops22h 56m

$578

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 3/17

2:26 pm-2:25 pm

1 stop21h 59m

George Town Owen Roberts Intl

Tue 3/24

3:30 pm-10:16 am

1 stop20h 46m

$599

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 3/16

10:55 pm-12:45 pm

1 stop11h 50m

George Town Owen Roberts Intl

Mon 3/23

4:45 pm-9:16 pm

2 stops30h 31m

$688

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/1

8:50 am-1:45 pm

2 stops25h 55m

George Town Owen Roberts Intl

Wed 3/4

2:25 pm-1:41 pm

2 stops26h 16m

$839

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

6:37 pm-1:30 pm

2 stops40h 53m

George Town Owen Roberts Intl

Sat 6/27

4:15 pm-1:24 pm

2 stops23h 09m

$877

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

2:36 pm-11:00 am

2 stops18h 24m

George Town Owen Roberts Intl

Sat 6/27

2:40 pm-10:11 pm

1 stop9h 31m

$1,073

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

10:20 pm-11:25 am

1 stop11h 05m

George Town Owen Roberts Intl

Sat 6/27

1:10 pm-10:53 pm

1 stop11h 43m

$1,151

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/15

10:55 pm-12:45 pm

1 stop11h 50m

$329

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/15

7:15 pm-1:35 pm

2 stops16h 20m

$353

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/15

11:06 am-4:50 pm

3 stops51h 44m

$5,187

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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 $409). 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 $578, United Airlines can have you in Cayman Islands from San Jose, California in 18h 26m. 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 $409). 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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