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Cayman Islands

$704+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
1 adult, Economy
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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 noviembre 6, 2025.

This Mytrip deal was found by Cheapflights users on 11/5. 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.
jue. 11/69:17 pmOAK - GCM
2 stops20h 58mMultiple Airlines
jue. 11/132:50 pmGCM - OAK
3 stops32h 07mMultiple Airlines
Deal found 11/5$1,396
This Southwest deal was found by Cheapflights users on 11/5. 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.
jue. 11/68:55 pmOAK - GCM
2 stops12h 50mSouthwest
jue. 11/131:30 pmGCM - OAK
2 stops13h 40mSouthwest
Deal found 11/5$1,840

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 noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$598
(Southwest)

Popular in

December

Cheapest in

September

Average price

$641
Provider with most accurate pricing for San Francisco-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-George Town Owen Roberts Intl flights.
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From Oakland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($76 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 November 2025
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 noviembre 6, 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

dom. 3/1

4:54 pm-12:35 pm

2 stops16h 41m

George Town Owen Roberts Intl

mar. 3/3

2:00 pm-11:57 am

2 stops24h 57m

$704

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

dom. 3/22

7:35 pm-11:40 am

2 stops14h 05m

George Town Owen Roberts Intl

dom. 3/29

12:55 pm-12:55 am

2 stops14h 00m

$801

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

dom. 3/22

11:17 pm-9:15 pm

2 stops19h 58m

George Town Owen Roberts Intl

dom. 3/29

7:00 am-9:35 pm

3 stops40h 35m

$1,095

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

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 $415). Flying from Oakland, 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 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 14h 05m. Fly via Delta or Southwest 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 $415). Flying from Oakland, 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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