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Cayman Islands

$724+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap 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 September 17, 2025.

Round-trip from

$724
(Delta)

Popular in

December

Cheapest in

February

Average price

$531
From Oakland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/16. 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 10/3112:30 pmOAK - GCM
2 stops21h 10mDelta
Fri 11/72:00 pmGCM - OAK
2 stops12h 53mDelta
Deal found 9/16$724

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 September 17, 2025.
Use the filters below to find and compare flights from Oakland to the Cayman Islands that are best for you.

Fly from

Oakland

Fly to

Cayman Islands

Route

Depart

Return

Price

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Fri 10/31

12:30 pm-11:40 am

2 stops21h 10m

George Town Owen Roberts Intl

Fri 11/7

2:00 pm-11:53 pm

2 stops12h 53m

$724

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 3/1

5:55 am-12:35 pm

2 stops27h 40m

George Town Owen Roberts Intl

Tue 3/3

2:00 pm-11:53 pm

2 stops12h 53m

$796

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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, January is the cheapest month in which you can book a flight from Oakland, California to Cayman Islands (average of $467). Flying from Oakland, California to Cayman Islands in March is currently the most expensive (average of $594). 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 21h 10m. Fly via Delta to get the fastest option. There are 2757 mi between Oakland, California and Cayman Islands.

  • 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, January is the cheapest month in which you can book a flight from Oakland, California to Cayman Islands (average of $467). Flying from Oakland, California to Cayman Islands in March is currently the most expensive (average of $594). 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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