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Cheap flights from Oakland, California to Grand Cayman from $586

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Oakland, California to Grand Cayman departing on 2/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Oakland, California to Grand Cayman

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:55 pm - 12:55 pm
OAK
-
GCM
15h 00m
2 stops
Southwest Logo
1:50 pm - 10:40 pm
GCM
-
OAK
11h 50m
2 stops
$586Southwest
Sun, Feb 8 - Sun, Feb 15
Southwest Logo
9:15 pm - 11:45 am
OAK
-
GCM
12h 30m
2 stops
Southwest Logo
12:40 pm - 10:35 pm
GCM
-
OAK
11h 55m
2 stops
$649Southwest
Sun, Mar 29 - Mon, Apr 6
Delta Logo
12:40 pm - 12:29 pm
OAK
-
GCM
20h 49m
2 stops
Delta Logo
1:54 pm - 11:51 pm
GCM
-
OAK
12h 57m
2 stops
$1,126Delta
Wed, Feb 25 - Wed, Mar 4

Southwest flights from Oakland, California to Grand Cayman

Our best Southwest deals on Oakland, California to Grand Cayman flight tickets
Southwest
Feb 8
OAK6:55 pmOakland
15h 00m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 15
GCM1:50 pmGeorge Town Owen Roberts Intl
11h 50m
2 stops
OAK10:40 pmOakland
$586
Southwest
Mar 29
OAK9:15 pmOakland
12h 30m
2 stops
GCM11:45 amGeorge Town Owen Roberts Intl
Apr 6
GCM12:40 pmGeorge Town Owen Roberts Intl
11h 55m
2 stops
OAK10:35 pmOakland
$649

momondo Fare Finder

 
Customize your flight search to find flights from Oakland, California 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, momondo users made 832,500 searches. Data last updated January 12, 2026.
Use the filters below to find and compare flights from Oakland, California to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 2/8

6:55 pm-12:55 pm

2 stops15h 00m

George Town Owen Roberts Intl

Sun 2/15

1:50 pm-10:40 pm

2 stops11h 50m

$586

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 3/29

9:15 pm-11:45 am

2 stops12h 30m

George Town Owen Roberts Intl

Mon 4/6

12:40 pm-10:35 pm

2 stops11h 55m

$649

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Wed 2/25

12:40 pm-12:29 pm

2 stops20h 49m

George Town Owen Roberts Intl

Wed 3/4

1:54 pm-11:51 pm

2 stops12h 57m

$1,126

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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How to get the cheapest flight ticket from Oakland, California to Grand Cayman

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Oakland, California to Grand Cayman flights?

No. A direct flight is the cheapest option for a flight between Oakland, California to Grand Cayman.

Cheap Oakland, California to Grand Cayman flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Grand Cayman

Fastest flight time

12h 30m

Direct flights

None
The fastest flight from Oakland, California to Grand Cayman takes 12h 30m
There are no direct flights from Oakland, California to Grand Cayman. There are no popular flight routes from Oakland, California to Grand Cayman.
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  • When did momondo last update prices for flights from Oakland Airport to Grand Cayman?

    Prices for flights from Oakland Airport to Grand Cayman are refreshed on a daily basis.

  • How old do you have to be to fly from Oakland Airport to Grand Cayman?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oakland Airport to Grand Cayman.

  • What documentation or ID do you need to fly to Grand Cayman?

    The travel and health documents required for your trip to Grand Cayman can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Grand Cayman. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Oakland, California to Grand Cayman?

Why use momondo?

Why should I use momondo to find a flight deal from Oakland to Grand Cayman?

Finding the right flight to Grand Cayman from Oakland is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Grand Cayman quick and easy, saving you time and money.

Can I find flights from Oakland to Grand Cayman with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Oakland to Grand Cayman flights to just show those with flexible booking policies.

How can momondo help me find flights from Oakland to Grand Cayman?

Once all potential Oakland to Grand Cayman flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Oakland to Grand Cayman right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Oakland to Grand Cayman flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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1 adult
Wed 2/11
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