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Cheap flights from San Jose, California to the Cayman Islands from $579

This is the cheapest round-trip 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 4/27. 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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0 bags

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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 - 12:30 pm
SJC
-
GCM
18h 45m2 stops
United Airlines Logo
1:35 pm - 1:26 pm
GCM
-
SJC
25h 51m2 stops
$579United Airlines
Mon, Apr 27 - Wed, Apr 29
United Airlines Logo
3:45 pm - 12:30 pm
SJC
-
GCM
18h 45m2 stops
United Airlines Logo
1:35 pm - 12:08 pm
GCM
-
SJC
24h 33m1 stop
$593United Airlines
Mon, Apr 27 - Wed, Apr 29
United Airlines Logo
3:45 pm - 11:45 am
SJC
-
GCM
18h 00m2 stops
United Airlines Logo
1:35 pm - 1:26 pm
GCM
-
SJC
25h 51m2 stops
$653United Airlines
Mon, Apr 27 - Wed, Apr 29
United Airlines Logo
3:45 pm - 12:30 pm
SJC
-
GCM
18h 45m2 stops
United Airlines Logo
1:35 pm - 12:08 pm
GCM
-
SJC
24h 33m1 stop
$667United Airlines
Mon, Apr 27 - Wed, Apr 29
KLM Logo
10:45 pm - 12:40 pm
SJC
-
GCM
10h 55m1 stop
KLM Logo
2:05 pm - 9:20 pm
GCM
-
SJC
10h 15m1 stop
$764KLM
Mon, Jan 19 - Tue, Jan 27
United Airlines Logo
8:40 am - 1:45 pm
SJC
-
GCM
26h 05m2 stops
United Airlines Logo
2:25 pm - 9:05 pm
GCM
-
SJC
33h 40m2 stops
$811United Airlines
Wed, Feb 11 - Wed, Feb 18
United Airlines Logo
6:30 pm - 12:30 pm
SJC
-
GCM
40h 00m2 stops
United Airlines Logo
1:45 pm - 9:11 pm
GCM
-
SJC
33h 26m2 stops
$1,016United Airlines
Thu, Jun 18 - Sat, Jun 27
United Airlines Logo
6:30 pm - 3:35 pm
SJC
-
GCM
43h 05m2 stops
United Airlines Logo
4:45 pm - 10:36 pm
GCM
-
SJC
31h 51m2 stops
$1,076United Airlines
Thu, Jun 18 - Sat, Jun 27
United Airlines Logo
7:00 am - 12:30 pm
SJC
-
GCM
27h 30m2 stops
United Airlines Logo
1:35 pm - 1:26 pm
GCM
-
SJC
25h 51m2 stops
$1,085United Airlines
Thu, Jun 11 - Thu, Jun 18
American Airlines Logo
11:24 pm - 1:15 pm
SJC
-
GCM
11h 51m1 stop
American Airlines Logo
3:15 pm - 9:13 am
GCM
-
SJC
19h 58m2 stops
$1,099American Airlines
Thu, Jun 18 - Sat, Jun 27

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 27
SJC3:45 pmSan Jose
18h 45m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Apr 29
GCM1:35 pmGeorge Town Owen Roberts Intl
25h 51m
2 stops
SJC1:26 pmSan Jose
$579
Find similar
United Airlines
Apr 27
SJC3:45 pmSan Jose
18h 45m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Apr 29
GCM1:35 pmGeorge Town Owen Roberts Intl
24h 33m
1 stop
SJC12:08 pmSan Jose
$593
Find similar
United Airlines
Apr 27
SJC3:45 pmSan Jose
18h 00m
2 stops
GCM11:45 amGeorge Town Owen Roberts Intl
Apr 29
GCM1:35 pmGeorge Town Owen Roberts Intl
25h 51m
2 stops
SJC1:26 pmSan Jose
$653
Find similar

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 18
SJC11:24 pmSan Jose
11h 51m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Jun 27
GCM3:15 pmGeorge Town Owen Roberts Intl
19h 58m
2 stops
SJC9:13 amSan Jose
$1,099
Find similar
American Airlines
Jun 18
SJC11:24 pmSan Jose
11h 51m
1 stop
GCM1:15 pmGeorge Town Owen Roberts Intl
Jun 27
GCM12:40 pmGeorge Town Owen Roberts Intl
11h 30m
2 stops
SJC10:10 pmSan Jose
$1,235
Find similar

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 December 22, 2025.
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

Mon 4/27

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Wed 4/29

1:35 pm-1:26 pm

2 stops25h 51m

$579

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/27

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Wed 4/29

1:35 pm-12:08 pm

1 stop24h 33m

$593

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/27

3:45 pm-11:45 am

2 stops18h 00m

George Town Owen Roberts Intl

Wed 4/29

1:35 pm-1:26 pm

2 stops25h 51m

$653

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/27

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Wed 4/29

1:35 pm-12:08 pm

1 stop24h 33m

$667

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 1/19

10:45 pm-12:40 pm

1 stop10h 55m

George Town Owen Roberts Intl

Tue 1/27

2:05 pm-9:20 pm

1 stop10h 15m

$764

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 2/11

8:40 am-1:45 pm

2 stops26h 05m

George Town Owen Roberts Intl

Wed 2/18

2:25 pm-9:05 pm

2 stops33h 40m

$811

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

6:30 pm-12:30 pm

2 stops40h 00m

George Town Owen Roberts Intl

Sat 6/27

1:45 pm-9:11 pm

2 stops33h 26m

$1,016

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

6:30 pm-3:35 pm

2 stops43h 05m

George Town Owen Roberts Intl

Sat 6/27

4:45 pm-10:36 pm

2 stops31h 51m

$1,076

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/11

7:00 am-12:30 pm

2 stops27h 30m

George Town Owen Roberts Intl

Thu 6/18

1:35 pm-1:26 pm

2 stops25h 51m

$1,085

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

11:24 pm-1:15 pm

1 stop11h 51m

George Town Owen Roberts Intl

Sat 6/27

3:15 pm-9:13 am

2 stops19h 58m

$1,099

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 day to depart on your flight to Cayman Islands?

Our data shows that Monday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $594. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Thursday is $677.

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 55m

Direct flights

None
The fastest flight from San Jose, California to Cayman Islands takes 10h 55m
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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