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Cheap flights from San Jose, California to the Cayman Islands from $321

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.
Southwest Logo
9:25 pm - 12:10 pm
SJC
-
GCM
12h 45m
2 stops
Southwest Logo
1:05 pm - 11:00 pm
GCM
-
SJC
11h 55m
2 stops
$487Southwest
Tue, Apr 14 - Tue, Apr 21
Delta Logo
11:00 pm - 12:00 pm
SJC
-
GCM
11h 00m
1 stop
Delta Logo
1:25 pm - 9:45 pm
GCM
-
SJC
10h 20m
1 stop
$556Delta
Tue, Apr 14 - Tue, Apr 21
Delta Logo
6:00 pm - 12:00 pm
SJC
-
GCM
16h 00m
2 stops
Delta Logo
1:25 pm - 9:45 pm
GCM
-
SJC
10h 20m
1 stop
$561Delta
Tue, Apr 14 - Tue, Apr 21
Delta Logo
10:20 pm - 11:26 am
SJC
-
GCM
11h 06m
1 stop
Delta Logo
12:56 pm - 10:41 pm
GCM
-
SJC
11h 45m
1 stop
$603Delta
Tue, Aug 4 - Thu, Aug 13
Delta Logo
3:45 pm - 11:26 am
SJC
-
GCM
17h 41m
2 stops
Delta Logo
12:56 pm - 12:09 pm
GCM
-
SJC
25h 13m
2 stops
$608Delta
Tue, Aug 4 - Tue, Aug 11
Delta Logo
5:00 pm - 11:26 am
SJC
-
GCM
16h 26m
2 stops
Delta Logo
12:56 pm - 10:41 pm
GCM
-
SJC
11h 45m
1 stop
$649Delta
Sat, Aug 8 - Tue, Aug 11
Delta Logo
10:20 pm - 11:42 am
SJC
-
GCM
11h 22m
1 stop
Delta Logo
12:56 pm - 10:41 pm
GCM
-
SJC
11h 45m
1 stop
$685Delta
Fri, Aug 7 - Mon, Aug 10
Delta Logo
6:10 pm - 11:42 am
SJC
-
GCM
15h 32m
2 stops
Delta Logo
12:56 pm - 10:41 pm
GCM
-
SJC
11h 45m
1 stop
$690Delta
Fri, Aug 7 - Mon, Aug 10
Delta Logo
10:20 pm - 11:26 am
SJC
-
GCM
11h 06m
1 stop
Delta Logo
12:56 pm - 10:41 pm
GCM
-
SJC
11h 45m
1 stop
$697Delta
Tue, Aug 4 - Wed, Aug 12
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
$737American Airlines
Thu, Jun 18 - Sat, Jun 27

Delta flights from San Jose, California to Cayman Islands

Our best Delta deals on San Jose, California to Cayman Islands flight tickets
Delta
Apr 14
SJC11:00 pmSan Jose
11h 00m
1 stop
GCM12:00 pmGeorge Town Owen Roberts Intl
Apr 21
GCM1:25 pmGeorge Town Owen Roberts Intl
10h 20m
1 stop
SJC9:45 pmSan Jose
$556
Delta
Apr 14
SJC6:00 pmSan Jose
16h 00m
2 stops
GCM12:00 pmGeorge Town Owen Roberts Intl
Apr 21
GCM1:25 pmGeorge Town Owen Roberts Intl
10h 20m
1 stop
SJC9:45 pmSan Jose
$561
Delta
Aug 4
SJC10:20 pmSan Jose
11h 06m
1 stop
GCM11:26 amGeorge Town Owen Roberts Intl
Aug 13
GCM12:56 pmGeorge Town Owen Roberts Intl
11h 45m
1 stop
SJC10:41 pmSan Jose
$603

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 13
SJC3:45 pmSan Jose
18h 00m
2 stops
GCM11:45 amGeorge Town Owen Roberts Intl
Apr 20
GCM1:35 pmGeorge Town Owen Roberts Intl
35h 06m
2 stops
SJC10:41 pmSan Jose
$742
United Airlines
Jun 28
SJC6:37 pmSan Jose
15h 53m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Jun 30
GCM1:35 pmGeorge Town Owen Roberts Intl
25h 49m
2 stops
SJC1:24 pmSan Jose
$790
United Airlines
Jun 27
SJC2:45 pmSan Jose
43h 45m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Jun 30
GCM1:35 pmGeorge Town Owen Roberts Intl
25h 49m
2 stops
SJC1:24 pmSan Jose
$810

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 28, 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 4/14

9:25 pm-12:10 pm

2 stops12h 45m

George Town Owen Roberts Intl

Tue 4/21

1:05 pm-11:00 pm

2 stops11h 55m

$487

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 4/14

11:00 pm-12:00 pm

1 stop11h 00m

George Town Owen Roberts Intl

Tue 4/21

1:25 pm-9:45 pm

1 stop10h 20m

$556

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 4/14

6:00 pm-12:00 pm

2 stops16h 00m

George Town Owen Roberts Intl

Tue 4/21

1:25 pm-9:45 pm

1 stop10h 20m

$561

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 8/4

10:20 pm-11:26 am

1 stop11h 06m

George Town Owen Roberts Intl

Thu 8/13

12:56 pm-10:41 pm

1 stop11h 45m

$603

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 8/4

3:45 pm-11:26 am

2 stops17h 41m

George Town Owen Roberts Intl

Tue 8/11

12:56 pm-12:09 pm

2 stops25h 13m

$608

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 8/8

5:00 pm-11:26 am

2 stops16h 26m

George Town Owen Roberts Intl

Tue 8/11

12:56 pm-10:41 pm

1 stop11h 45m

$649

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 8/7

10:20 pm-11:42 am

1 stop11h 22m

George Town Owen Roberts Intl

Mon 8/10

12:56 pm-10:41 pm

1 stop11h 45m

$685

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 8/7

6:10 pm-11:42 am

2 stops15h 32m

George Town Owen Roberts Intl

Mon 8/10

12:56 pm-10:41 pm

1 stop11h 45m

$690

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 8/4

10:20 pm-11:26 am

1 stop11h 06m

George Town Owen Roberts Intl

Wed 8/12

12:56 pm-10:41 pm

1 stop11h 45m

$697

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

$737

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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?

American Airlines and Delta are the most popular carriers 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 48% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 3 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

10h 57m

Direct flights

None
The fastest flight from San Jose, California to Cayman Islands takes 10h 57m
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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