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Cayman Islands

$267+ Cheap flights from Oakland, CA (OAK) 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
Jul 10 — Jul 171
Fri 7/10
Fri 7/17
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 June 10, 2026.

This Southwest deal was found by Cheapflights users on 6/7. 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.
Sat 6/208:35 pm
OAK
-
GCM
2 stops13h 20m
Southwest
Sun 6/2812:50 pm
GCM
-
OAK
2 stops13h 25m
Southwest
Deal found 6/7$798
This Mytrip deal was found by Cheapflights users on 6/7. 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.
Sat 6/2011:30 pm
OAK
-
GCM
3 stops33h 55m
Multiple Airlines
Sun 6/284:45 pm
GCM
-
OAK
3 stops30h 59m
Multiple Airlines
Deal found 6/7$1,741
This Delta deal was found by Cheapflights users on 6/9. 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 12/225:05 pm
OAK
-
GCM
2 stops16h 35m
Delta
Thu 12/311:00 pm
GCM
-
OAK
2 stops13h 56m
Delta
Deal found 6/9$5,338

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 June 10, 2026.

Round-trip from

$798
(Southwest)

One-way from

$267
(Southwest)

Popular in

December

Cheapest in

September

Average price

$780
From Oakland to Cayman Islands
Search Deals
One-way flight from Oakland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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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 June 10, 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

Sat 6/20

8:35 pm-11:55 am

2 stops13h 20m

George Town Owen Roberts Intl

Sun 6/28

12:50 pm-12:15 am

2 stops13h 25m

$798

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 6/20

11:30 pm-11:25 am

3 stops33h 55m

George Town Owen Roberts Intl

Sun 6/28

4:45 pm-9:44 pm

3 stops30h 59m

$1,741
Cheapest one-way
Quickest one-way

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Wed 7/15

7:30 pm-11:55 am

2 stops14h 25m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

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
No data available for this route at this time. Please check back soon.

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 20m. Fly via Southwest 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.

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