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Cayman Islands

$164+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — GCM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$624
(Delta)

One-way from

$164
(Kiwi.com)
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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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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/6. 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 9/185:05 pmSJC - GCM
2 stops16h 35mDelta
Sun 9/2712:55 pmGCM - SJC
1 stop11h 46mDelta
Deal found 1/6$558
This American Airlines deal was found by Cheapflights users on 1/6. 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 9/182:25 pmSJC - GCM
2 stops18h 25mAmerican Airlines
Sun 9/2712:35 pmGCM - SJC
2 stops25h 04mAmerican Airlines
Deal found 1/6$563
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/202:07 pmSJC - GCM
1 stop22h 18mAmerican Airlines
Fri 2/273:45 pmGCM - SJC
2 stops21h 26mAmerican Airlines
Deal found 1/6$570
This Delta deal was found by Cheapflights users on 1/6. 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 3/159:16 amSJC - GCM
2 stops24h 31mDelta
Sat 3/212:30 pmGCM - SJC
2 stops19h 46mDelta
Deal found 1/6$624
This American Airlines deal was found by Cheapflights users on 1/8. 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 4/56:00 amSJC - GCM
1 stop7h 35mAmerican Airlines
Sat 4/114:03 pmGCM - SJC
2 stops22h 03mAmerican Airlines
Deal found 1/8$800
This Delta deal was found by Cheapflights users on 1/6. 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 3/146:10 amSJC - GCM
2 stops27h 37mDelta
Sat 3/212:30 pmGCM - SJC
2 stops19h 46mDelta
Deal found 1/6$818
This Delta deal was found by Cheapflights users on 1/8. 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.
Mon 4/66:25 pmSJC - GCM
2 stops15h 22mDelta
Fri 4/102:55 pmGCM - SJC
2 stops23h 36mDelta
Deal found 1/8$846
This United Airlines deal was found by Cheapflights users on 1/6. 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 1/204:00 pmSJC - GCM
2 stops18h 15mUnited Airlines
Thu 1/222:50 pmGCM - SJC
2 stops33h 06mUnited Airlines
Deal found 1/6$865

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 January 8, 2026.
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

Fri 2/20

2:07 pm-3:25 pm

1 stop22h 18m

George Town Owen Roberts Intl

Fri 2/27

3:45 pm-10:11 am

2 stops21h 26m

$570

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 3/14

6:10 am-11:47 am

2 stops27h 37m

George Town Owen Roberts Intl

Sat 3/21

2:30 pm-8:16 am

2 stops19h 46m

$818

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Mon 4/6

6:25 pm-11:47 am

2 stops15h 22m

George Town Owen Roberts Intl

Fri 4/10

2:55 pm-12:31 pm

2 stops23h 36m

$846

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 3/15

9:16 am-11:47 am

2 stops24h 31m

George Town Owen Roberts Intl

Sat 3/21

2:30 pm-12:08 pm

1 stop23h 38m

$852

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 1/20

4:00 pm-1:15 pm

2 stops18h 15m

George Town Owen Roberts Intl

Thu 1/22

2:50 pm-1:39 pm

2 stops25h 49m

$865

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 4/5

9:15 pm-11:45 am

2 stops12h 30m

George Town Owen Roberts Intl

Sat 4/11

1:05 pm-7:40 am

2 stops20h 35m

$922

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sun 2/22

8:50 am-1:45 pm

2 stops25h 55m

George Town Owen Roberts Intl

Sun 3/1

2:50 pm-9:05 pm

2 stops33h 15m

$924

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Sat 3/14

3:49 pm-12:45 pm

2 stops42h 56m

George Town Owen Roberts Intl

Sat 3/21

4:45 pm-9:16 pm

2 stops30h 31m

$951

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Thu 2/5

12:34 pm-1:38 pm

3 stops46h 04m

$164

San JoseGeorge Town

SJC - GCM

SJCGCM

San Jose

Tue 4/14

10:45 pm-11:24 am

1 stop10h 39m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 17 results
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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 $407). 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 $570, American Airlines can have you in Cayman Islands from San Jose, California in 22h 18m. 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 $407). 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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