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Cayman Islands

$224+ Cheap flights from San Jose, CA (SJC) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap 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 December 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/2. 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 12/302:06 pmSJC - GCM
1 stop22h 20mAmerican Airlines
Mon 1/53:45 pmGCM - SJC
2 stops22h 12mAmerican Airlines
Deal found 12/2$722
This United Airlines deal was found by Cheapflights users on 12/2. 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.
Tue 12/3010:30 pmSJC - GCM
1 stop12h 15mUnited Airlines
Sun 1/45:45 pmGCM - SJC
2 stops24h 25mUnited Airlines
Deal found 12/2$844
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Mon 12/226:00 amSJC - GCM
2 stops26h 57mAmerican Airlines
Thu 1/13:11 pmGCM - SJC
2 stops21h 52mAmerican Airlines
Deal found 12/3$1,096
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Mon 12/226:00 amSJC - GCM
1 stop30h 25mAmerican Airlines
Fri 1/23:45 pmGCM - SJC
2 stops20h 36mAmerican Airlines
Deal found 12/3$1,115
This Delta deal was found by Cheapflights users on 12/3. 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.
Fri 12/196:35 amSJC - GCM
2 stops25h 54mDelta
Thu 1/11:52 pmGCM - SJC
2 stops21h 32mDelta
Deal found 12/3$1,122
This Delta deal was found by Cheapflights users on 12/2. 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 stop10h 41mDelta
Mon 1/52:05 pmGCM - SJC
1 stop10h 15mDelta
Deal found 12/2$1,145
This Delta deal was found by Cheapflights users on 12/3. 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.
Sat 12/205:55 amSJC - GCM
2 stops27h 41mDelta
Thu 1/11:52 pmGCM - SJC
2 stops21h 32mDelta
Deal found 12/3$1,162
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Fri 12/196:10 amSJC - GCM
2 stops29h 39mAmerican Airlines
Fri 1/23:45 pmGCM - SJC
2 stops20h 36mAmerican Airlines
Deal found 12/3$1,167
This American Airlines deal was found by Cheapflights users on 12/3. 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 12/2310:53 amSJC - GCM
2 stops22h 12mAmerican Airlines
Fri 1/23:45 pmGCM - SJC
2 stops20h 36mAmerican Airlines
Deal found 12/3$1,171
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Fri 12/196:10 amSJC - GCM
2 stops29h 39mAmerican Airlines
Thu 1/14:30 pmGCM - SJC
1 stop20h 33mAmerican Airlines
Deal found 12/3$1,193

Find 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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$552
(Delta)

One-way from

$224
(Delta)
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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One-way flight 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 December 4, 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

Sun 2/8

10:45 pm-12:40 pm

1 stop10h 55m

George Town Owen Roberts Intl

Sat 2/14

1:54 pm-9:18 pm

1 stop10h 24m

$552

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 1/4

2:06 pm-3:25 pm

1 stop22h 19m

George Town Owen Roberts Intl

Mon 1/12

12:50 pm-9:24 am

2 stops23h 34m

$569

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 1/4

2:29 pm-4:00 pm

2 stops22h 31m

George Town Owen Roberts Intl

Mon 1/12

2:50 pm-1:39 pm

2 stops25h 49m

$604

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 2/2

11:51 am-12:05 pm

2 stops21h 14m

George Town Owen Roberts Intl

Fri 2/6

1:05 pm-9:24 am

2 stops23h 19m

$667

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 2/8

4:00 pm-1:15 pm

2 stops18h 15m

George Town Owen Roberts Intl

Sat 2/14

5:30 pm-1:41 pm

2 stops23h 11m

$667

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 2/9

6:25 pm-12:40 pm

2 stops15h 15m

George Town Owen Roberts Intl

Sat 2/14

12:25 pm-9:18 pm

1 stop11h 53m

$676

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

$676

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 2/3

10:45 pm-12:40 pm

1 stop10h 55m

George Town Owen Roberts Intl

Fri 2/6

2:05 pm-10:57 am

2 stops23h 52m

$676

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 2/8

8:05 pm-12:40 pm

2 stops13h 35m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

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 $419). 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 $552, Delta can have you in Cayman Islands from San Jose, California in 10h 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 $419). 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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