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Cheap flights from San Jose, California to the Cayman Islands from $171

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 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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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 - 11:45 am
SJC
-
GCM
18h 00m
2 stops
United Airlines Logo
1:50 pm - 10:41 pm
GCM
-
SJC
10h 51m
1 stop
$650United Airlines
Mon, Apr 20 - Thu, Apr 23
United Airlines Logo
3:45 pm - 11:45 am
SJC
-
GCM
18h 00m
2 stops
United Airlines Logo
1:50 pm - 9:07 pm
GCM
-
SJC
57h 17m
2 stops
$668United Airlines
Mon, Apr 20 - Thu, Apr 23
United Airlines Logo
3:45 pm - 11:45 am
SJC
-
GCM
18h 00m
2 stops
United Airlines Logo
1:50 pm - 10:41 pm
GCM
-
SJC
10h 51m
1 stop
$684United Airlines
Mon, Apr 20 - Thu, Apr 23
United Airlines Logo
3:45 pm - 11:45 am
SJC
-
GCM
18h 00m
2 stops
United Airlines Logo
1:50 pm - 9:07 pm
GCM
-
SJC
57h 17m
2 stops
$703United Airlines
Mon, Apr 20 - Thu, Apr 23
United Airlines Logo
3:45 pm - 12:30 pm
SJC
-
GCM
18h 45m
2 stops
United Airlines Logo
1:50 pm - 10:41 pm
GCM
-
SJC
10h 51m
1 stop
$722United Airlines
Mon, Apr 20 - Thu, Apr 23
United Airlines Logo
3:45 pm - 12:30 pm
SJC
-
GCM
18h 45m
2 stops
United Airlines Logo
1:50 pm - 9:07 pm
GCM
-
SJC
57h 17m
2 stops
$740United Airlines
Mon, Apr 20 - Thu, Apr 23
United Airlines Logo
6:37 pm - 1:30 pm
SJC
-
GCM
40h 53m
2 stops
United Airlines Logo
4:10 pm - 1:25 pm
GCM
-
SJC
23h 15m
2 stops
$903United Airlines
Thu, Jun 18 - Sat, Jun 27
United Airlines Logo
6:37 pm - 1:30 pm
SJC
-
GCM
40h 53m
2 stops
United Airlines Logo
4:45 pm - 1:25 pm
GCM
-
SJC
22h 40m
2 stops
$928United Airlines
Thu, Jun 18 - Sat, Jun 27
Delta Logo
10:20 pm - 11:41 am
SJC
-
GCM
11h 21m
1 stop
Delta Logo
12:56 pm - 10:41 pm
GCM
-
SJC
11h 45m
1 stop
$939Delta
Thu, Sep 3 - Tue, Sep 8
United Airlines Logo
3:45 pm - 12:30 pm
SJC
-
GCM
18h 45m
2 stops
United Airlines Logo
1:50 pm - 1:35 pm
GCM
-
SJC
25h 45m
2 stops
$957United Airlines
Mon, Apr 13 - Sat, Apr 18

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
SJC2:34 pmSan Jose
18h 56m
2 stops
GCM11:30 amGeorge Town Owen Roberts Intl
Jun 27
GCM11:56 amGeorge Town Owen Roberts Intl
13h 17m
2 stops
SJC11:13 pmSan Jose
$982
American Airlines
Jun 18
SJC2:34 pmSan Jose
18h 27m
2 stops
GCM11:01 amGeorge Town Owen Roberts Intl
Jun 27
GCM11:56 amGeorge Town Owen Roberts Intl
13h 17m
2 stops
SJC11:13 pmSan Jose
$987
American Airlines
Jun 18
SJC2:34 pmSan Jose
21h 01m
1 stop
GCM1:35 pmGeorge Town Owen Roberts Intl
Jun 27
GCM11:22 amGeorge Town Owen Roberts Intl
13h 51m
1 stop
SJC11:13 pmSan Jose
$1,051

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 20
SJC3:45 pmSan Jose
18h 00m
2 stops
GCM11:45 amGeorge Town Owen Roberts Intl
Apr 23
GCM1:50 pmGeorge Town Owen Roberts Intl
10h 51m
1 stop
SJC10:41 pmSan Jose
$650
United Airlines
Apr 20
SJC3:45 pmSan Jose
18h 00m
2 stops
GCM11:45 amGeorge Town Owen Roberts Intl
Apr 23
GCM1:50 pmGeorge Town Owen Roberts Intl
57h 17m
2 stops
SJC9:07 pmSan Jose
$668
United Airlines
Apr 20
SJC3:45 pmSan Jose
18h 00m
2 stops
GCM11:45 amGeorge Town Owen Roberts Intl
Apr 23
GCM1:50 pmGeorge Town Owen Roberts Intl
10h 51m
1 stop
SJC10:41 pmSan Jose
$684

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 March 7, 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

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/20

3:45 pm-11:45 am

2 stops18h 00m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-10:41 pm

1 stop10h 51m

$650

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/20

3:45 pm-11:45 am

2 stops18h 00m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-9:07 pm

2 stops57h 17m

$668

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/20

3:45 pm-11:45 am

2 stops18h 00m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-10:41 pm

1 stop10h 51m

$684

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/20

3:45 pm-11:45 am

2 stops18h 00m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-9:07 pm

2 stops57h 17m

$703

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/20

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-10:41 pm

1 stop10h 51m

$722

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/20

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-9:07 pm

2 stops57h 17m

$740

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

6:37 pm-1:30 pm

2 stops40h 53m

George Town Owen Roberts Intl

Sat 6/27

4:10 pm-1:25 pm

2 stops23h 15m

$903

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 6/18

6:37 pm-1:30 pm

2 stops40h 53m

George Town Owen Roberts Intl

Sat 6/27

4:45 pm-1:25 pm

2 stops22h 40m

$928
Quickest round-trip

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 9/3

10:20 pm-11:41 am

1 stop11h 21m

George Town Owen Roberts Intl

Tue 9/8

12:56 pm-10:41 pm

1 stop11h 45m

$939

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/13

3:45 pm-12:30 pm

2 stops18h 45m

George Town Owen Roberts Intl

Sat 4/18

1:50 pm-1:35 pm

2 stops25h 45m

$957

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 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

11h 21m

Direct flights

None
The fastest flight from San Jose, California to Cayman Islands takes 11h 21m
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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