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Cheap flights from Oakland, California to the Cayman Islands from $600

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 the Cayman Islands departing on 7/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Oakland, California to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 pm - 11:55 am
OAK
-
GCM
16h 25m
2 stops
Southwest Logo
11:25 am - 12:15 am
GCM
-
OAK
14h 50m
2 stops
$600Southwest
Mon, Jul 6 - Sat, Jul 11
Southwest Logo
7:40 pm - 11:55 am
OAK
-
GCM
14h 15m
2 stops
Southwest Logo
12:50 pm - 6:55 am
GCM
-
OAK
20h 05m
2 stops
$617Southwest
Mon, Jun 15 - Tue, Jun 23
Delta Logo
6:00 am - 11:34 am
OAK
-
GCM
27h 34m
2 stops
Delta Logo
12:59 pm - 9:41 pm
GCM
-
OAK
34h 42m
2 stops
$1,036Delta
Mon, Jun 29 - Fri, Jul 3
Delta Logo
6:00 am - 11:34 am
OAK
-
GCM
27h 34m
2 stops
Delta Logo
12:59 pm - 9:41 pm
GCM
-
OAK
34h 42m
2 stops
$1,175Delta
Sun, Jun 28 - Fri, Jul 3
Delta Logo
12:33 pm - 11:34 am
OAK
-
GCM
21h 01m
2 stops
Delta Logo
12:59 pm - 9:41 pm
GCM
-
OAK
34h 42m
2 stops
$1,223Delta
Sat, Jun 27 - Fri, Jul 3
Delta Logo
6:00 am - 11:34 am
OAK
-
GCM
27h 34m
2 stops
Delta Logo
12:59 pm - 11:53 am
GCM
-
OAK
24h 54m
2 stops
$1,310Delta
Mon, Jun 29 - Sat, Jul 4
Delta Logo
6:00 am - 11:34 am
OAK
-
GCM
27h 34m
2 stops
Delta Logo
12:59 pm - 11:54 pm
GCM
-
OAK
36h 55m
2 stops
$1,449Delta
Sun, Jun 28 - Sat, Jul 4
Delta Logo
12:33 pm - 11:34 am
OAK
-
GCM
21h 01m
2 stops
Delta Logo
12:59 pm - 11:53 am
GCM
-
OAK
24h 54m
2 stops
$1,502Delta
Sat, Jun 27 - Sat, Jul 4
Delta Logo
12:33 pm - 11:34 am
OAK
-
GCM
21h 01m
2 stops
Delta Logo
12:59 pm - 11:54 pm
GCM
-
OAK
12h 55m
2 stops
$2,640Delta
Sat, Jun 27 - Sun, Jul 5
Delta Logo
12:33 pm - 11:34 am
OAK
-
GCM
21h 01m
2 stops
Delta Logo
12:59 pm - 11:54 pm
GCM
-
OAK
12h 55m
2 stops
$2,692Delta
Sun, Jun 28 - Sun, Jul 5

Delta flights from Oakland, California to Cayman Islands

Our best Delta deals on Oakland, California to Cayman Islands flight tickets
Delta
May 23
OAK5:55 pmOakland
15h 59m
2 stops
GCM11:54 amGeorge Town Owen Roberts Intl
May 28
GCM1:19 pmGeorge Town Owen Roberts Intl
24h 29m
2 stops
OAK11:48 amOakland
$650
Delta
May 19
OAK5:05 pmOakland
16h 49m
2 stops
GCM11:54 amGeorge Town Owen Roberts Intl
May 28
GCM1:19 pmGeorge Town Owen Roberts Intl
24h 29m
2 stops
OAK11:48 amOakland
$736
Delta
May 19
OAK5:05 pmOakland
16h 49m
2 stops
GCM11:54 amGeorge Town Owen Roberts Intl
May 23
GCM1:19 pmGeorge Town Owen Roberts Intl
24h 29m
2 stops
OAK11:48 amOakland
$778

Southwest flights from Oakland, California to Cayman Islands

Our best Southwest deals on Oakland, California to Cayman Islands flight tickets
Southwest
Jul 6
OAK5:30 pmOakland
16h 25m
2 stops
GCM11:55 amGeorge Town Owen Roberts Intl
Jul 11
GCM11:25 amGeorge Town Owen Roberts Intl
14h 50m
2 stops
OAK12:15 amOakland
$600
Southwest
Jun 15
OAK7:40 pmOakland
14h 15m
2 stops
GCM11:55 amGeorge Town Owen Roberts Intl
Jun 23
GCM12:50 pmGeorge Town Owen Roberts Intl
20h 05m
2 stops
OAK6:55 amOakland
$617

momondo Fare Finder

 
Customize your flight search to find flights from Oakland, California 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, momondo users made 832,500 searches. Data last updated May 15, 2026.
Use the filters below to find and compare flights from Oakland, California 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

Mon 7/6

5:30 pm-11:55 am

2 stops16h 25m

George Town Owen Roberts Intl

Sat 7/11

11:25 am-12:15 am

2 stops14h 50m

$600

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Mon 6/15

7:40 pm-11:55 am

2 stops14h 15m

George Town Owen Roberts Intl

Tue 6/23

12:50 pm-6:55 am

2 stops20h 05m

$617

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Mon 6/29

6:00 am-11:34 am

2 stops27h 34m

George Town Owen Roberts Intl

Fri 7/3

12:59 pm-9:41 pm

2 stops34h 42m

$1,036

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 6/28

6:00 am-11:34 am

2 stops27h 34m

George Town Owen Roberts Intl

Fri 7/3

12:59 pm-9:41 pm

2 stops34h 42m

$1,175

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 6/27

12:33 pm-11:34 am

2 stops21h 01m

George Town Owen Roberts Intl

Fri 7/3

12:59 pm-9:41 pm

2 stops34h 42m

$1,223

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Mon 6/29

6:00 am-11:34 am

2 stops27h 34m

George Town Owen Roberts Intl

Sat 7/4

12:59 pm-11:53 am

2 stops24h 54m

$1,310

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 6/28

6:00 am-11:34 am

2 stops27h 34m

George Town Owen Roberts Intl

Sat 7/4

12:59 pm-11:54 pm

2 stops36h 55m

$1,449

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 6/27

12:33 pm-11:34 am

2 stops21h 01m

George Town Owen Roberts Intl

Sat 7/4

12:59 pm-11:53 am

2 stops24h 54m

$1,502

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 6/27

12:33 pm-11:34 am

2 stops21h 01m

George Town Owen Roberts Intl

Sun 7/5

12:59 pm-11:54 pm

2 stops12h 55m

$2,640

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 6/28

12:33 pm-11:34 am

2 stops21h 01m

George Town Owen Roberts Intl

Sun 7/5

12:59 pm-11:54 pm

2 stops12h 55m

$2,692

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to the Cayman Islands from

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

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

What airlines fly to Cayman Islands?

American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Cayman Islands from Oakland, California according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 3 different airlines that fly to Cayman Islands on a routine basis, so you have a few additional options to choose from.

Cheap Oakland, California to Cayman Islands flight deals and tips

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

Fastest flight time

14h 15m

Direct flights

None
The fastest flight from Oakland, California to Cayman Islands takes 14h 15m
There are no direct flights from Oakland, California to Cayman Islands. There are no popular flight routes from Oakland, California to Cayman Islands.
Search flight deals

Frequently asked questions about flying from Oakland, California to the Cayman Islands

  • When did momondo last update prices for flights from Oakland Airport to Cayman Islands?

    Prices for flights from Oakland Airport to Cayman Islands refresh daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Oakland Airport to Cayman Islands.

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

    The necessary travel and health documents for your Cayman Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Oakland to Cayman Islands. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Oakland to Cayman Islands on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Cayman Islands from Oakland.

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

If you are not ready to book a flight from Oakland to Cayman Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Cayman Islands and let you know when they change.

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