Latest deals
Insights
FAQs
Price Alerts

Cheap flights from San Jose, California to the Cayman Islands from $329

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.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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.
American Airlines Logo
7:15 pm - 2:14 pm
SJC
-
GCM
15h 59m
2 stops
American Airlines Logo
2:15 pm - 10:16 am
GCM
-
SJC
22h 01m
2 stops
$555American Airlines
Wed, Mar 4 - Sun, Mar 8
American Airlines Logo
7:15 pm - 2:14 pm
SJC
-
GCM
15h 59m
2 stops
American Airlines Logo
3:30 pm - 10:16 am
GCM
-
SJC
20h 46m
1 stop
$567American Airlines
Wed, Mar 4 - Sun, Mar 8
American Airlines Logo
11:01 am - 3:25 pm
SJC
-
GCM
25h 24m
1 stop
American Airlines Logo
3:30 pm - 10:16 am
GCM
-
SJC
20h 46m
1 stop
$575American Airlines
Wed, Mar 4 - Sun, Mar 8
Delta Logo
10:55 pm - 11:54 am
SJC
-
GCM
10h 59m
2 stops
Delta Logo
1:19 pm - 10:55 pm
GCM
-
SJC
11h 36m
1 stop
$634Delta
Sun, May 17 - Sun, May 24
Delta Logo
10:00 pm - 11:54 am
SJC
-
GCM
11h 54m
1 stop
Delta Logo
1:19 pm - 10:55 pm
GCM
-
SJC
11h 36m
1 stop
$667Delta
Sun, May 17 - Sun, May 24
American Airlines Logo
11:06 am - 2:25 pm
SJC
-
GCM
25h 19m
1 stop
American Airlines Logo
2:15 pm - 10:16 am
GCM
-
SJC
22h 01m
2 stops
$716American Airlines
Thu, Mar 19 - Thu, Mar 26
American Airlines Logo
11:06 am - 2:25 pm
SJC
-
GCM
25h 19m
1 stop
American Airlines Logo
3:30 pm - 10:16 am
GCM
-
SJC
20h 46m
1 stop
$725American Airlines
Thu, Mar 19 - Thu, Mar 26
American Airlines Logo
2:08 pm - 10:40 am
SJC
-
GCM
18h 32m
2 stops
American Airlines Logo
2:15 pm - 10:16 am
GCM
-
SJC
22h 01m
2 stops
$774American Airlines
Thu, Mar 19 - Thu, Mar 26
United Airlines Logo
8:50 am - 1:45 pm
SJC
-
GCM
25h 55m
2 stops
United Airlines Logo
2:25 pm - 1:41 pm
GCM
-
SJC
26h 16m
2 stops
$792United Airlines
Sun, Mar 1 - Wed, Mar 4
American Airlines Logo
2:08 pm - 4:16 pm
SJC
-
GCM
24h 08m
1 stop
American Airlines Logo
2:15 pm - 10:16 am
GCM
-
SJC
22h 01m
2 stops
$794American Airlines
Fri, Mar 20 - Fri, Mar 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
Mar 1
SJC8:50 amSan Jose
25h 55m
2 stops
GCM1:45 pmGeorge Town Owen Roberts Intl
Mar 4
GCM2:25 pmGeorge Town Owen Roberts Intl
26h 16m
2 stops
SJC1:41 pmSan Jose
$792
United Airlines
Mar 1
SJC8:50 amSan Jose
25h 25m
2 stops
GCM1:15 pmGeorge Town Owen Roberts Intl
Mar 4
GCM2:25 pmGeorge Town Owen Roberts Intl
26h 16m
2 stops
SJC1:41 pmSan Jose
$839
United Airlines
Jun 18
SJC6:37 pmSan Jose
40h 53m
2 stops
GCM1:30 pmGeorge Town Owen Roberts Intl
Jun 27
GCM4:15 pmGeorge Town Owen Roberts Intl
31h 04m
2 stops
SJC9:19 pmSan Jose
$919

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
Mar 4
SJC7:15 pmSan Jose
15h 59m
2 stops
GCM2:14 pmGeorge Town Owen Roberts Intl
Mar 8
GCM2:15 pmGeorge Town Owen Roberts Intl
22h 01m
2 stops
SJC10:16 amSan Jose
$555
American Airlines
Mar 4
SJC7:15 pmSan Jose
15h 59m
2 stops
GCM2:14 pmGeorge Town Owen Roberts Intl
Mar 8
GCM3:30 pmGeorge Town Owen Roberts Intl
20h 46m
1 stop
SJC10:16 amSan Jose
$567
American Airlines
Mar 4
SJC11:01 amSan Jose
25h 24m
1 stop
GCM3:25 pmGeorge Town Owen Roberts Intl
Mar 8
GCM3:30 pmGeorge Town Owen Roberts Intl
20h 46m
1 stop
SJC10:16 amSan Jose
$575

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 4, 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

Wed 3/4

7:15 pm-2:14 pm

2 stops15h 59m

George Town Owen Roberts Intl

Sun 3/8

2:15 pm-10:16 am

2 stops22h 01m

$555

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 3/4

7:15 pm-2:14 pm

2 stops15h 59m

George Town Owen Roberts Intl

Sun 3/8

3:30 pm-10:16 am

1 stop20h 46m

$567

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Wed 3/4

11:01 am-3:25 pm

1 stop25h 24m

George Town Owen Roberts Intl

Sun 3/8

3:30 pm-10:16 am

1 stop20h 46m

$575

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 5/17

10:55 pm-11:54 am

2 stops10h 59m

George Town Owen Roberts Intl

Sun 5/24

1:19 pm-10:55 pm

1 stop11h 36m

$634

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 5/17

10:00 pm-11:54 am

1 stop11h 54m

George Town Owen Roberts Intl

Sun 5/24

1:19 pm-10:55 pm

1 stop11h 36m

$667

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 3/19

11:06 am-2:25 pm

1 stop25h 19m

George Town Owen Roberts Intl

Thu 3/26

2:15 pm-10:16 am

2 stops22h 01m

$716

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 3/19

11:06 am-2:25 pm

1 stop25h 19m

George Town Owen Roberts Intl

Thu 3/26

3:30 pm-10:16 am

1 stop20h 46m

$725

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 3/19

2:08 pm-10:40 am

2 stops18h 32m

George Town Owen Roberts Intl

Thu 3/26

2:15 pm-10:16 am

2 stops22h 01m

$774

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/1

8:50 am-1:45 pm

2 stops25h 55m

George Town Owen Roberts Intl

Wed 3/4

2:25 pm-1:41 pm

2 stops26h 16m

$792

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 3/20

2:08 pm-4:16 pm

1 stop24h 08m

George Town Owen Roberts Intl

Fri 3/27

2:15 pm-10:16 am

2 stops22h 01m

$794

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

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 and American Airlines 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 46% 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

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.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 3/6
Fri 3/13
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $185
Flights to Cayman Bracfrom $322
Flights to Little Caymanfrom $349