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Grand Cayman

$679+ Cheap flights from Oakland, CA (OAK) to Grand Cayman

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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap flight deals from Oakland to Grand Cayman

Cheapest flights from Oakland to Grand Cayman
Explore the most affordable flight options available from Oakland to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Southwest deal was found by Cheapflights users on 12/18. 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 12/278:20 pmOAK - GCM
2 stops13h 15mSouthwest
Sun 1/41:30 pmGCM - OAK
2 stops13h 05mSouthwest
Deal found 12/18$1,775

Find flight deals from Oakland to Grand Cayman

Keep the following information in mind while searching for Oakland to Grand Cayman flight deals. Data was last updated December 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$679
(Southwest)

Popular in

December

Cheapest in

February

Average price

$1,007
Provider with most accurate pricing for San Francisco-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for San Francisco-George Town Owen Roberts Intl flights.
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From Oakland to Grand Cayman
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Grand Cayman 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 December 21, 2025.
Use the filters below to find and compare flights from Oakland to Grand Cayman that are best for you.

Fly from

Oakland

Fly to

Grand Cayman

Route

Depart

Return

Price

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 3/28

7:35 pm-12:00 pm

2 stops14h 25m

George Town Owen Roberts Intl

Sat 4/4

2:55 pm-7:20 am

2 stops18h 25m

$679

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Thu 6/11

5:05 pm-11:25 am

2 stops16h 20m

George Town Owen Roberts Intl

Thu 6/18

12:40 pm-11:49 pm

2 stops13h 09m

$1,047

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Best time to book a flight from Oakland to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman

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

Currently, February is the cheapest month in which you can book a flight from Oakland, California to Grand Cayman (average of $408). Flying from Oakland, California to Grand Cayman 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 Grand Cayman. 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 Grand Cayman?

    If you book a flight to Grand Cayman from Oakland, you will be flying from Oakland, which is the city’s only airport. Oakland (OAK) is located 7.0 mi from the center of Oakland.

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

    For as low as $679, Southwest can have you in Grand Cayman from Oakland, California in 14h 25m. The distance between Oakland, California and Grand Cayman is about 2757 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Oakland to Grand Cayman that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Grand Cayman 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 Grand Cayman?

    Currently, February is the cheapest month in which you can book a flight from Oakland, California to Grand Cayman (average of $408). Flying from Oakland, California to Grand Cayman 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.

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