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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
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Find flight deals from San Jose to Cayman Islands

Cheapest flights from San Jose to Cayman Islands
Explore the most affordable flight options available from San Jose to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/25. 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.
Tue 12/307:17 pmSJC - GCM
2 stops16h 32mAmerican Airlines
Mon 1/53:45 pmGCM - SJC
2 stops20h 39mAmerican Airlines
Deal found 11/25$657
This Delta deal was found by Cheapflights users on 11/25. 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.
Sun 12/710:25 pmSJC - GCM
1 stop11h 10mDelta
Fri 12/121:50 pmGCM - SJC
1 stop12h 05mDelta
Deal found 11/25$766
This Delta deal was found by Cheapflights users on 11/25. 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.
Tue 12/3010:55 pmSJC - GCM
1 stop12h 32mDelta
Mon 1/52:05 pmGCM - SJC
1 stop10h 15mDelta
Deal found 11/25$941
This Mytrip deal was found by Cheapflights users on 11/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:15 amSJC - GCM
3 stops27h 29mMultiple Airlines
Fri 12/121:30 pmGCM - SJC
3 stops28h 27mMultiple Airlines
Deal found 11/25$1,115
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Sun 12/76:10 amSJC - GCM
2 stops11h 05mAmerican Airlines
Fri 12/128:45 amGCM - SJC
3 stops14h 51mAmerican Airlines
Deal found 11/25$2,631

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 November 26, 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.
Search Deals
Provider most trusted by Cheapflights users for San Jose-George Town Owen Roberts Intl flights.
Search Deals
From San Jose to Cayman Islands
Search Deals

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 November 26, 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

Mon 2/23

4:22 pm-2:46 pm

2 stops19h 24m

George Town Owen Roberts Intl

Thu 2/26

3:45 pm-10:11 am

2 stops21h 26m

$605

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 2/23

6:30 pm-12:29 pm

2 stops14h 59m

George Town Owen Roberts Intl

Thu 2/26

1:54 pm-9:18 pm

1 stop10h 24m

$645

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Fri 1/9

9:10 pm-4:20 pm

2 stops16h 10m

George Town Owen Roberts Intl

Fri 1/16

2:50 pm-1:38 pm

2 stops25h 48m

$687

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 12/30

2:06 pm-3:26 pm

1 stop22h 20m

George Town Owen Roberts Intl

Mon 1/5

3:45 pm-9:24 am

2 stops20h 39m

$726

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 12/7

10:25 pm-12:35 pm

1 stop11h 10m

George Town Owen Roberts Intl

Fri 12/12

1:50 pm-10:55 pm

1 stop12h 05m

$766

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 12/7

7:55 pm-12:35 pm

2 stops13h 40m

George Town Owen Roberts Intl

Fri 12/12

1:30 pm-10:55 pm

2 stops12h 25m

$771

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/23

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 $645, American Airlines can have you in Cayman Islands from San Jose, California in 14h 59m. 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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