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Cayman Islands

$605+ Cheap flights from San Jose, CA (SJC) to the Cayman Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
dic. 19 — dic. 261
vie. 12/19
vie. 12/26
1 adult, Economy
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Find flight deals from San Jose to Cayman Islands

Best flights from San Jose to Cayman Islands
Discover carefully curated flight deals from San Jose to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated noviembre 19, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/232:12 pmSJC - GCM
2 stops18h 52mAmerican Airlines
jue. 2/2612:54 pmGCM - SJC
2 stops24h 17mAmerican Airlines
Deal found 11/18$605
This Delta deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/231:26 pmSJC - GCM
2 stops20h 09mDelta
jue. 2/262:00 pmGCM - SJC
1 stop10h 20mDelta
Deal found 11/18$645
This Southwest deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/137:35 pmSJC - GCM
2 stops13h 55mSouthwest
dom. 2/221:50 pmGCM - SJC
2 stops21h 25mSouthwest
Deal found 11/18$951
This United Airlines deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1010:55 pmSJC - GCM
1 stop11h 50mUnited Airlines
mié. 3/114:45 pmGCM - SJC
2 stops22h 56mUnited Airlines
Deal found 11/17$1,331
This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/132:12 pmSJC - GCM
1 stop22h 18mAmerican Airlines
dom. 2/223:45 pmGCM - SJC
2 stops21h 26mAmerican Airlines
Deal found 11/18$986
This American Airlines deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1012:28 pmSJC - GCM
1 stop22h 51mAmerican Airlines
mié. 3/113:35 pmGCM - SJC
1 stop22h 19mAmerican Airlines
Deal found 11/17$2,724

Cheap flight deals from San Jose to Cayman Islands

Keep the following information in mind while searching for San Jose to Cayman Islands flight deals. Data was last updated noviembre 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$605
(American Airlines)
Provider with most accurate pricing for San Jose-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for San Jose-George Town Owen Roberts Intl flights.
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From San Jose to Cayman Islands
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Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose 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, Cheapflights users made 2,558,603 searches. Data last updated noviembre 19, 2025.
Use the filters below to find and compare flights from San Jose to the Cayman Islands that are best for you.

Fly from

San Jose

Fly to

Cayman Islands

Route

Depart

Return

Price

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

lun. 2/23

2:12 pm-12:04 pm

2 stops18h 52m

George Town Owen Roberts Intl

jue. 2/26

12:54 pm-10:11 am

2 stops24h 17m

$605

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

lun. 2/23

1:26 pm-12:35 pm

2 stops20h 09m

George Town Owen Roberts Intl

jue. 2/26

2:00 pm-9:20 pm

1 stop10h 20m

$645

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

vie. 2/13

7:35 pm-12:30 pm

2 stops13h 55m

George Town Owen Roberts Intl

dom. 2/22

1:50 pm-8:15 am

2 stops21h 25m

$951

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

vie. 2/13

2:12 pm-3:30 pm

1 stop22h 18m

George Town Owen Roberts Intl

dom. 2/22

3:45 pm-10:11 am

2 stops21h 26m

$986

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

mar. 3/10

10:55 pm-12:45 pm

1 stop11h 50m

George Town Owen Roberts Intl

mié. 3/11

4:45 pm-1:41 pm

2 stops22h 56m

$1,331

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

mar. 3/10

12:28 pm-1:19 pm

1 stop22h 51m

George Town Owen Roberts Intl

mié. 3/11

3:35 pm-11:54 am

1 stop22h 19m

$2,724

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Best time to book a flight from San Jose to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from San Jose with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Jose to the Cayman Islands

What is the cheapest month to book a flight from San Jose, California to Cayman Islands?

Currently, February is the cheapest month in which you can book a flight from San Jose, California to Cayman Islands (average of $416). Flying from San Jose, California to Cayman Islands in August is currently the most expensive (average of $553). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Jose to Cayman Islands?

    For a flight from San Jose to Cayman Islands, you will be flying from San Jose. San Jose (SJC) is just 2.9 mi from the center of the city.

  • How long is the flight from San Jose, California to Cayman Islands?

    For as low as $951, American Airlines can have you in Cayman Islands from San Jose, California in 13h 55m. Airlines will cover a distance of 2735 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from San Jose to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on San Jose to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Cayman Islands.

  • Can I find deals for business class flights from San Jose to Cayman Islands?

    Yes. Cheapflights offers flight deals from San Jose to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Jose, California to Cayman Islands?

    Currently, February is the cheapest month in which you can book a flight from San Jose, California to Cayman Islands (average of $416). Flying from San Jose, California to Cayman Islands in August is currently the most expensive (average of $553). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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