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Cayman Islands

$546+ Cheap flights from Oakland, CA (OAK) 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
Apr 30 — May 71
Thu 4/30
Thu 5/7
1 adult, Economy
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Cheap flight deals from Oakland to Cayman Islands

Cheapest flights from Oakland to Cayman Islands
Explore the most affordable flight options available from Oakland to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 31, 2026.

This Southwest deal was found by Cheapflights users on 3/28. 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.
Tue 4/219:05 pm
OAK
-
GCM
2 stops13h 05m
Southwest
Tue 4/281:05 pm
GCM
-
OAK
2 stops11h 20m
Southwest
Deal found 3/28$546
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 5/148:55 pm
OAK
-
GCM
2 stops13h 15m
Southwest
Thu 5/211:05 pm
GCM
-
OAK
2 stops13h 20m
Southwest
Deal found 3/30$585
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 4/14:49 pm
OAK
-
GCM
2 stops16h 58m
Delta
Mon 4/61:12 pm
GCM
-
OAK
2 stops12h 34m
Delta
Deal found 3/30$776
This Delta deal was found by Cheapflights users on 3/29. 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 5/295:05 pm
OAK
-
GCM
2 stops16h 49m
Delta
Wed 6/31:19 pm
GCM
-
OAK
2 stops36h 38m
Delta
Deal found 3/29$1,141
This Delta deal was found by Cheapflights users on 3/29. 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 5/296:00 am
OAK
-
GCM
2 stops27h 54m
Delta
Thu 6/41:19 pm
GCM
-
OAK
2 stops12h 38m
Delta
Deal found 3/29$1,235

Find flight deals from Oakland to Cayman Islands

Keep the following information in mind while searching for Oakland to Cayman Islands flight deals. Data was last updated March 31, 2026.

Round-trip from

$546
(Southwest)

Popular in

December

Cheapest in

September

Average price

$693
From Oakland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($151 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland 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 March 31, 2026.
Use the filters below to find and compare flights from Oakland to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Tue 4/21

9:05 pm-12:10 pm

2 stops13h 05m

George Town Owen Roberts Intl

Tue 4/28

1:05 pm-10:25 pm

2 stops11h 20m

$546

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Thu 5/14

8:55 pm-12:10 pm

2 stops13h 15m

George Town Owen Roberts Intl

Thu 5/21

1:05 pm-12:25 am

2 stops13h 20m

$585

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Fri 5/29

5:05 pm-11:54 am

2 stops16h 49m

George Town Owen Roberts Intl

Wed 6/3

1:19 pm-11:57 pm

2 stops36h 38m

$1,141

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Fri 5/29

6:00 am-11:54 am

2 stops27h 54m

George Town Owen Roberts Intl

Thu 6/4

1:19 pm-11:57 pm

2 stops12h 38m

$1,235

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 5/30

6:00 am-11:54 am

2 stops27h 54m

George Town Owen Roberts Intl

Thu 6/4

1:19 pm-11:57 pm

2 stops12h 38m

$1,235

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Sorted by cheapest first

Best time to book a flight from Oakland to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Oakland 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 Oakland to the Cayman Islands

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

Currently, February is the cheapest month in which you can book a flight from Oakland, California to Cayman Islands (average of $405). Flying from Oakland, California to Cayman Islands in August is currently the most expensive (average of $545). 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 Oakland 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 Oakland to Cayman Islands?

    Located just 7.0 mi from the city center, Oakland (OAK) is the airport most travelers will use when flying to Cayman Islands from Oakland.

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

    There are many flights that can get you from Oakland, California to Cayman Islands in 13h 05m. Fly via Southwest or Delta to get the fastest option. There are 2757 mi between Oakland, California and Cayman Islands. 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 Oakland to Cayman Islands that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland 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 Oakland, California to Cayman Islands?

    Currently, February is the cheapest month in which you can book a flight from Oakland, California to Cayman Islands (average of $405). Flying from Oakland, California to Cayman Islands in August is currently the most expensive (average of $545). 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.

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