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Cheap flights from San Jose, California to the Cayman Islands from $294

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Jose, California to the Cayman Islands departing on 3/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from San Jose, California to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
3:45 pm - 11:45 am
SJC
-
GCM
18h 00m
2 stops
United Airlines Logo
4:09 pm - 12:00 pm
GCM
-
SJC
21h 51m
2 stops
$722United Airlines
Tue, Apr 28 - Sat, May 9
Southwest Logo
7:40 pm - 11:50 am
SJC
-
GCM
14h 10m
2 stops
Southwest Logo
12:45 pm - 11:25 pm
GCM
-
SJC
12h 40m
2 stops
$740Southwest
Wed, Jun 24 - Thu, Jul 2
American Airlines Logo
12:38 pm - 11:02 am
SJC
-
GCM
20h 24m
2 stops
American Airlines Logo
2:40 pm - 10:11 pm
GCM
-
SJC
9h 31m
1 stop
$765American Airlines
Wed, Jun 24 - Thu, Jul 2
American Airlines Logo
2:35 pm - 1:37 pm
SJC
-
GCM
21h 02m
1 stop
American Airlines Logo
2:40 pm - 10:11 pm
GCM
-
SJC
9h 31m
1 stop
$778American Airlines
Wed, Jun 24 - Thu, Jul 2
American Airlines Logo
2:35 pm - 11:28 am
SJC
-
GCM
18h 53m
2 stops
American Airlines Logo
4:07 pm - 10:56 am
GCM
-
SJC
20h 49m
2 stops
$784American Airlines
Thu, Jun 18 - Sat, Jun 27
American Airlines Logo
2:35 pm - 11:02 am
SJC
-
GCM
18h 27m
2 stops
American Airlines Logo
4:07 pm - 10:56 am
GCM
-
SJC
20h 49m
2 stops
$788American Airlines
Thu, Jun 18 - Sat, Jun 27
American Airlines Logo
2:35 pm - 11:28 am
SJC
-
GCM
18h 53m
2 stops
American Airlines Logo
4:07 pm - 10:56 am
GCM
-
SJC
20h 49m
2 stops
$804American Airlines
Thu, Jun 18 - Sat, Jun 27
American Airlines Logo
2:35 pm - 1:37 pm
SJC
-
GCM
21h 02m
1 stop
American Airlines Logo
4:07 pm - 10:56 am
GCM
-
SJC
20h 49m
2 stops
$825American Airlines
Thu, Jun 18 - Sat, Jun 27
United Airlines Logo
3:45 pm - 12:30 pm
SJC
-
GCM
18h 45m
2 stops
United Airlines Logo
1:35 pm - 10:36 pm
GCM
-
SJC
35h 01m
2 stops
$886United Airlines
Sun, Apr 5 - Thu, Apr 9
United Airlines Logo
3:55 pm - 1:15 pm
SJC
-
GCM
18h 20m
2 stops
United Airlines Logo
2:25 pm - 1:41 pm
GCM
-
SJC
26h 16m
2 stops
$888United Airlines
Sun, Mar 1 - Wed, Mar 4

United Airlines flights from San Jose, California to Cayman Islands

Our best United Airlines deals on San Jose, California to Cayman Islands flight tickets
United Airlines
Apr 28
SJC3:45 pmSan Jose
18h 00m
2 stops
GCM11:45 amGeorge Town Owen Roberts Intl
May 9
GCM4:09 pmGeorge Town Owen Roberts Intl
21h 51m
2 stops
SJC12:00 pmSan Jose
$722
United Airlines
Jun 27
SJC6:37 pmSan Jose
39h 53m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Jul 8
GCM1:35 pmGeorge Town Owen Roberts Intl
25h 49m
2 stops
SJC1:24 pmSan Jose
$741
United Airlines
Jun 27
SJC2:32 pmSan Jose
43h 58m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Jul 3
GCM1:35 pmGeorge Town Owen Roberts Intl
25h 49m
2 stops
SJC1:24 pmSan Jose
$764

American Airlines flights from San Jose, California to Cayman Islands

Our best American Airlines deals on San Jose, California to Cayman Islands flight tickets
American Airlines
Jun 30
SJC4:25 pmSan Jose
17h 03m
2 stops
GCM11:28 amGeorge Town Owen Roberts Intl
Jul 6
GCM2:10 pmGeorge Town Owen Roberts Intl
22h 52m
2 stops
SJC11:02 amSan Jose
$608
American Airlines
Jun 28
SJC2:35 pmSan Jose
18h 53m
2 stops
GCM11:28 amGeorge Town Owen Roberts Intl
Jul 8
GCM12:00 pmGeorge Town Owen Roberts Intl
25h 02m
2 stops
SJC11:02 amSan Jose
$718
American Airlines
Jun 28
SJC2:35 pmSan Jose
18h 53m
2 stops
GCM11:28 amGeorge Town Owen Roberts Intl
Jul 5
GCM2:10 pmGeorge Town Owen Roberts Intl
25h 36m
2 stops
SJC1:46 pmSan Jose
$723

momondo Fare Finder

 
Customize your flight search to find flights from San Jose, California 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, momondo users made 832,500 searches. Data last updated February 20, 2026.
Use the filters below to find and compare flights from San Jose, California to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 4/28

3:45 pm-11:45 am

2 stops18h 00m

George Town Owen Roberts Intl

Sat 5/9

4:09 pm-12:00 pm

2 stops21h 51m

$722

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 6/24

7:40 pm-11:50 am

2 stops14h 10m

George Town Owen Roberts Intl

Thu 7/2

12:45 pm-11:25 pm

2 stops12h 40m

$740

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 6/24

12:38 pm-11:02 am

2 stops20h 24m

George Town Owen Roberts Intl

Thu 7/2

2:40 pm-10:11 pm

1 stop9h 31m

$765

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 6/24

2:35 pm-1:37 pm

1 stop21h 02m

George Town Owen Roberts Intl

Thu 7/2

2:40 pm-10:11 pm

1 stop9h 31m

$778

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

2:35 pm-11:28 am

2 stops18h 53m

George Town Owen Roberts Intl

Sat 6/27

4:07 pm-10:56 am

2 stops20h 49m

$784

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

2:35 pm-11:02 am

2 stops18h 27m

George Town Owen Roberts Intl

Sat 6/27

4:07 pm-10:56 am

2 stops20h 49m

$788

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

2:35 pm-11:28 am

2 stops18h 53m

George Town Owen Roberts Intl

Sat 6/27

4:07 pm-10:56 am

2 stops20h 49m

$804

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

2:35 pm-1:37 pm

1 stop21h 02m

George Town Owen Roberts Intl

Sat 6/27

4:07 pm-10:56 am

2 stops20h 49m

$825

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 4/5

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Thu 4/9

1:35 pm-10:36 pm

2 stops35h 01m

$886

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/1

3:55 pm-1:15 pm

2 stops18h 20m

George Town Owen Roberts Intl

Wed 3/4

2:25 pm-1:41 pm

2 stops26h 16m

$888

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from San Jose, California to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from San Jose to Cayman Islands?

United Airlines is the most popular carrier operating from San Jose to Cayman Islands

What airlines fly to Cayman Islands?

United Airlines, American Airlines and JetBlue are the top three most popular airlines that fly to Cayman Islands from San Jose, California according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 4 different airlines that fly to Cayman Islands on a routine basis, so you have a few additional options to choose from.

Cheap San Jose, California to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Jose, California to Cayman Islands

Fastest flight time

12h 10m

Direct flights

None
The fastest flight from San Jose, California to Cayman Islands takes 12h 10m
There are no direct flights from San Jose, California to Cayman Islands. There are no popular flight routes from San Jose, California to Cayman Islands.
Search flight deals

  • When did momondo last update prices for flights from San Jose Airport to Cayman Islands?

    Prices for flights from San Jose Airport to Cayman Islands refresh daily.

  • How old do you have to be to fly from San Jose Airport to Cayman Islands?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Jose Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The travel and health documents you'll need for your trip to Cayman Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from San Jose to Cayman Islands?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Cayman Islands from San Jose.

Can I find flights from San Jose to Cayman Islands with flexible booking policies on momondo?

momondo does allow users to show only those flights to Cayman Islands from San Jose which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from San Jose to Cayman Islands?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Jose to Cayman Islands.

I’m not ready to book a flight from San Jose to Cayman Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of San Jose to Cayman Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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