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Cheap flights from San Jose, California to the Cayman Islands from $464

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 1/16. 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.
Delta Logo
2:06 pm - 11:00 am
SJC
-
GCM
17h 54m1 stop
Delta Logo
12:22 pm - 9:20 pm
GCM
-
SJC
11h 58m1 stop
$464Delta
Fri, Jan 16 - Sat, Jan 24
Delta Logo
9:15 am - 11:00 am
SJC
-
GCM
22h 45m2 stops
Delta Logo
2:05 pm - 8:32 am
GCM
-
SJC
21h 27m2 stops
$469Delta
Fri, Jan 16 - Fri, Jan 23
American Airlines Logo
12:50 pm - 11:26 am
SJC
-
GCM
19h 36m2 stops
American Airlines Logo
3:45 pm - 10:57 am
GCM
-
SJC
22h 12m2 stops
$519American Airlines
Mon, Feb 2 - Tue, Feb 10
American Airlines Logo
2:32 pm - 11:26 am
SJC
-
GCM
17h 54m2 stops
American Airlines Logo
3:45 pm - 9:24 am
GCM
-
SJC
20h 39m2 stops
$538American Airlines
Fri, Jan 23 - Fri, Jan 30
Delta Logo
1:40 pm - 12:40 pm
SJC
-
GCM
20h 00m2 stops
Delta Logo
2:05 pm - 9:20 pm
GCM
-
SJC
10h 15m1 stop
$543Delta
Sun, Jan 18 - Wed, Jan 21
American Airlines Logo
2:32 pm - 3:25 pm
SJC
-
GCM
21h 53m1 stop
American Airlines Logo
8:50 am - 10:49 pm
GCM
-
SJC
16h 59m2 stops
$550American Airlines
Fri, Jan 23 - Fri, Jan 30
American Airlines Logo
12:50 pm - 11:26 am
SJC
-
GCM
19h 36m2 stops
American Airlines Logo
4:25 pm - 1:42 pm
GCM
-
SJC
24h 17m1 stop
$551American Airlines
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
8:30 pm - 12:10 pm
SJC
-
GCM
13h 40m2 stops
Southwest Logo
1:05 pm - 11:30 pm
GCM
-
SJC
12h 25m2 stops
$557Southwest
Mon, Apr 6 - Mon, Apr 13
American Airlines Logo
7:16 pm - 11:26 am
SJC
-
GCM
13h 10m2 stops
American Airlines Logo
8:50 am - 10:49 pm
GCM
-
SJC
16h 59m2 stops
$575American Airlines
Mon, Jan 19 - Thu, Jan 22
American Airlines Logo
2:32 pm - 11:50 am
SJC
-
GCM
18h 18m2 stops
American Airlines Logo
3:45 pm - 10:57 am
GCM
-
SJC
22h 12m2 stops
$580American Airlines
Sun, Jan 18 - Sun, Jan 25

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
Feb 2
SJC12:50 pmSan Jose
19h 36m
2 stops
GCM11:26 amGeorge Town Owen Roberts Intl
Feb 10
GCM3:45 pmGeorge Town Owen Roberts Intl
22h 12m
2 stops
SJC10:57 amSan Jose
$519
Find similar
American Airlines
Jan 23
SJC2:32 pmSan Jose
17h 54m
2 stops
GCM11:26 amGeorge Town Owen Roberts Intl
Jan 30
GCM3:45 pmGeorge Town Owen Roberts Intl
20h 39m
2 stops
SJC9:24 amSan Jose
$538
Find similar
American Airlines
Jan 23
SJC2:32 pmSan Jose
21h 53m
1 stop
GCM3:25 pmGeorge Town Owen Roberts Intl
Jan 30
GCM8:50 amGeorge Town Owen Roberts Intl
16h 59m
2 stops
SJC10:49 pmSan Jose
$550
Find similar

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
Feb 23
SJC3:55 pmSan Jose
18h 20m
2 stops
GCM1:15 pmGeorge Town Owen Roberts Intl
Feb 26
GCM2:50 pmGeorge Town Owen Roberts Intl
33h 16m
2 stops
SJC9:06 pmSan Jose
$597
Find similar
United Airlines
Feb 23
SJC3:55 pmSan Jose
18h 20m
2 stops
GCM1:15 pmGeorge Town Owen Roberts Intl
Feb 26
GCM2:50 pmGeorge Town Owen Roberts Intl
49h 51m
2 stops
SJC1:41 pmSan Jose
$648
Find similar
United Airlines
Feb 3
SJC4:00 pmSan Jose
42h 45m
2 stops
GCM1:45 pmGeorge Town Owen Roberts Intl
Feb 10
GCM2:25 pmGeorge Town Owen Roberts Intl
26h 14m
2 stops
SJC1:39 pmSan Jose
$657
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 11, 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

Fri 1/16

2:06 pm-11:00 am

1 stop17h 54m

George Town Owen Roberts Intl

Sat 1/24

12:22 pm-9:20 pm

1 stop11h 58m

$464

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 1/16

9:15 am-11:00 am

2 stops22h 45m

George Town Owen Roberts Intl

Fri 1/23

2:05 pm-8:32 am

2 stops21h 27m

$469

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 2/2

12:50 pm-11:26 am

2 stops19h 36m

George Town Owen Roberts Intl

Tue 2/10

3:45 pm-10:57 am

2 stops22h 12m

$519

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 1/23

2:32 pm-11:26 am

2 stops17h 54m

George Town Owen Roberts Intl

Fri 1/30

3:45 pm-9:24 am

2 stops20h 39m

$538

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 1/18

1:40 pm-12:40 pm

2 stops20h 00m

George Town Owen Roberts Intl

Wed 1/21

2:05 pm-9:20 pm

1 stop10h 15m

$543

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 1/23

2:32 pm-3:25 pm

1 stop21h 53m

George Town Owen Roberts Intl

Fri 1/30

8:50 am-10:49 pm

2 stops16h 59m

$550

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 1/10

12:50 pm-11:26 am

2 stops19h 36m

George Town Owen Roberts Intl

Sat 1/17

4:25 pm-1:42 pm

1 stop24h 17m

$551

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/6

8:30 pm-12:10 pm

2 stops13h 40m

George Town Owen Roberts Intl

Mon 4/13

1:05 pm-11:30 pm

2 stops12h 25m

$557

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 1/19

7:16 pm-11:26 am

2 stops13h 10m

George Town Owen Roberts Intl

Thu 1/22

8:50 am-10:49 pm

2 stops16h 59m

$575

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 1/18

2:32 pm-11:50 am

2 stops18h 18m

George Town Owen Roberts Intl

Sun 1/25

3:45 pm-10:57 am

2 stops22h 12m

$580

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 59m

Direct flights

None
The fastest flight from San Jose, California to Cayman Islands takes 10h 59m
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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