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Cheap flights from San Jose, California to the Cayman Islands from $286

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 9/19. 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
10:20 pm - 11:40 am
SJC
-
GCM
11h 20m
1 stop
Delta Logo
12:55 pm - 10:41 pm
GCM
-
SJC
11h 46m
1 stop
$627Delta
Sun, Sep 20 - Sat, Sep 26
Delta Logo
5:05 pm - 11:40 am
SJC
-
GCM
16h 35m
2 stops
Delta Logo
12:55 pm - 10:41 pm
GCM
-
SJC
11h 46m
1 stop
$632Delta
Sun, Sep 20 - Sat, Sep 26
American Airlines Logo
2:35 pm - 11:30 am
SJC
-
GCM
18h 55m
2 stops
American Airlines Logo
3:35 pm - 11:12 pm
GCM
-
SJC
9h 37m
1 stop
$682American Airlines
Thu, Jun 18 - Sat, Jun 27
American Airlines Logo
2:35 pm - 11:30 am
SJC
-
GCM
18h 55m
2 stops
American Airlines Logo
5:12 pm - 10:55 am
GCM
-
SJC
19h 43m
2 stops
$692American Airlines
Wed, Jun 24 - Sun, Jun 28
American Airlines Logo
2:23 pm - 11:25 am
SJC
-
GCM
19h 02m
2 stops
American Airlines Logo
2:41 pm - 10:48 am
GCM
-
SJC
22h 07m
1 stop
$697American Airlines
Sat, Jul 25 - Tue, Aug 4
Delta Logo
10:00 pm - 11:54 am
SJC
-
GCM
11h 54m
1 stop
Delta Logo
12:59 pm - 10:57 pm
GCM
-
SJC
11h 58m
1 stop
$722Delta
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
9:25 pm - 12:10 pm
SJC
-
GCM
12h 45m
2 stops
Southwest Logo
12:50 pm - 10:25 pm
GCM
-
SJC
11h 35m
2 stops
$727Southwest
Tue, Jun 2 - Tue, Jun 9
Delta Logo
10:00 pm - 11:54 am
SJC
-
GCM
11h 54m
1 stop
Delta Logo
12:59 pm - 10:57 pm
GCM
-
SJC
11h 58m
1 stop
$767Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
11:45 am - 11:54 am
SJC
-
GCM
22h 09m
2 stops
Delta Logo
12:59 pm - 9:14 am
GCM
-
SJC
22h 15m
2 stops
$772Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
1:40 pm - 11:54 am
SJC
-
GCM
20h 14m
2 stops
Delta Logo
12:59 pm - 10:57 pm
GCM
-
SJC
11h 58m
1 stop
$777Delta
Tue, Jun 2 - Wed, Jun 10

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
SJC2:35 pmSan Jose
18h 55m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
Jun 27
GCM3:35 pmGeorge Town Owen Roberts Intl
9h 37m
1 stop
SJC11:12 pmSan Jose
$682
American Airlines
Jun 24
SJC2:35 pmSan Jose
18h 55m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
Jun 28
GCM5:12 pmGeorge Town Owen Roberts Intl
19h 43m
2 stops
SJC10:55 amSan Jose
$692
American Airlines
Jul 25
SJC2:23 pmSan Jose
19h 02m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Aug 4
GCM2:41 pmGeorge Town Owen Roberts Intl
22h 07m
1 stop
SJC10:48 amSan Jose
$697

Delta flights from San Jose, California to Cayman Islands

Our best Delta deals on San Jose, California to Cayman Islands flight tickets
Delta
Sep 20
SJC10:20 pmSan Jose
11h 20m
1 stop
GCM11:40 amGeorge Town Owen Roberts Intl
Sep 26
GCM12:55 pmGeorge Town Owen Roberts Intl
11h 46m
1 stop
SJC10:41 pmSan Jose
$627
Delta
Sep 20
SJC5:05 pmSan Jose
16h 35m
2 stops
GCM11:40 amGeorge Town Owen Roberts Intl
Sep 26
GCM12:55 pmGeorge Town Owen Roberts Intl
11h 46m
1 stop
SJC10:41 pmSan Jose
$632
Delta
Jun 3
SJC10:00 pmSan Jose
11h 54m
1 stop
GCM11:54 amGeorge Town Owen Roberts Intl
Jun 10
GCM12:59 pmGeorge Town Owen Roberts Intl
11h 58m
1 stop
SJC10:57 pmSan Jose
$722

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 May 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

Cheapest round-trip
Quickest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 9/20

10:20 pm-11:40 am

1 stop11h 20m

George Town Owen Roberts Intl

Sat 9/26

12:55 pm-10:41 pm

1 stop11h 46m

$627

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 9/20

5:05 pm-11:40 am

2 stops16h 35m

George Town Owen Roberts Intl

Sat 9/26

12:55 pm-10:41 pm

1 stop11h 46m

$632

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

2:35 pm-11:30 am

2 stops18h 55m

George Town Owen Roberts Intl

Sat 6/27

3:35 pm-11:12 pm

1 stop9h 37m

$682

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 6/24

2:35 pm-11:30 am

2 stops18h 55m

George Town Owen Roberts Intl

Sun 6/28

5:12 pm-10:55 am

2 stops19h 43m

$692

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 7/25

2:23 pm-11:25 am

2 stops19h 02m

George Town Owen Roberts Intl

Tue 8/4

2:41 pm-10:48 am

1 stop22h 07m

$697

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 6/3

10:00 pm-11:54 am

1 stop11h 54m

George Town Owen Roberts Intl

Wed 6/10

12:59 pm-10:57 pm

1 stop11h 58m

$722

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 6/2

9:25 pm-12:10 pm

2 stops12h 45m

George Town Owen Roberts Intl

Tue 6/9

12:50 pm-10:25 pm

2 stops11h 35m

$727

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 6/3

10:00 pm-11:54 am

1 stop11h 54m

George Town Owen Roberts Intl

Mon 6/8

12:59 pm-10:57 pm

1 stop11h 58m

$767

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 6/3

11:45 am-11:54 am

2 stops22h 09m

George Town Owen Roberts Intl

Mon 6/8

12:59 pm-9:14 am

2 stops22h 15m

$772

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 6/2

1:40 pm-11:54 am

2 stops20h 14m

George Town Owen Roberts Intl

Wed 6/10

12:59 pm-10:57 pm

1 stop11h 58m

$777

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 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?

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

What airlines fly to Cayman Islands?

American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Cayman Islands from San Jose, California according to our data. American Airlines is the first choice among our users, with 47% 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

11h 20m

Direct flights

None
The fastest flight from San Jose, California to Cayman Islands takes 11h 20m
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

Frequently asked questions about flying from San Jose, California to the Cayman Islands

  • 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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