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Cayman Islands

$497+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
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Cheap flight deals from Oakland to Cayman Islands

Best flights from Oakland to Cayman Islands
Discover carefully curated flight deals from Oakland to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 31, 2025.

This Delta deal was found by Cheapflights users on 12/29. 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.
Fri 1/235:55 amOAK - GCM
2 stops26h 02mDelta
Mon 1/262:05 pmGCM - OAK
2 stops24h 47mDelta
Deal found 12/29$497
This Delta deal was found by Cheapflights users on 12/29. 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.
Fri 1/2312:33 pmOAK - GCM
2 stops19h 24mDelta
Tue 1/272:05 pmGCM - OAK
2 stops12h 48mDelta
Deal found 12/29$567
This Delta deal was found by Cheapflights users on 12/29. 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.
Thu 1/225:55 amOAK - GCM
2 stops27h 45mDelta
Mon 1/262:05 pmGCM - OAK
2 stops24h 47mDelta
Deal found 12/29$567
This Delta deal was found by Cheapflights users on 12/29. 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.
Thu 1/225:55 amOAK - GCM
2 stops27h 45mDelta
Tue 1/272:05 pmGCM - OAK
2 stops12h 48mDelta
Deal found 12/29$637
This Delta deal was found by Cheapflights users on 12/29. 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.
Fri 2/65:55 amOAK - GCM
2 stops26h 24mDelta
Sun 2/82:05 pmGCM - OAK
2 stops24h 47mDelta
Deal found 12/29$684
This Delta deal was found by Cheapflights users on 12/29. 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.
Thu 2/512:33 pmOAK - GCM
2 stops21h 07mDelta
Sun 2/82:05 pmGCM - OAK
2 stops24h 47mDelta
Deal found 12/29$684
This Delta deal was found by Cheapflights users on 12/29. 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.
Sat 1/2412:33 pmOAK - GCM
2 stops21h 07mDelta
Tue 1/272:05 pmGCM - OAK
2 stops12h 48mDelta
Deal found 12/29$697
This Delta deal was found by Cheapflights users on 12/29. 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.
Mon 4/135:55 amOAK - GCM
2 stops27h 29mDelta
Mon 4/2012:45 pmGCM - OAK
2 stops37h 04mDelta
Deal found 12/29$725
This Delta deal was found by Cheapflights users on 12/29. 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 4/145:55 amOAK - GCM
2 stops27h 29mDelta
Mon 4/2012:45 pmGCM - OAK
2 stops37h 04mDelta
Deal found 12/29$725
This Delta deal was found by Cheapflights users on 12/29. 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.
Fri 2/65:55 amOAK - GCM
2 stops26h 24mDelta
Mon 2/92:05 pmGCM - OAK
2 stops29h 09mDelta
Deal found 12/29$725
This Delta deal was found by Cheapflights users on 12/29. 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.
Fri 1/2312:33 pmOAK - GCM
2 stops19h 46mDelta
Sun 1/252:05 pmGCM - OAK
2 stops12h 48mDelta
Deal found 12/29$772
This Delta deal was found by Cheapflights users on 12/29. 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.
Thu 2/55:55 amOAK - GCM
2 stops27h 45mDelta
Sat 2/72:05 pmGCM - OAK
2 stops24h 47mDelta
Deal found 12/29$772

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 December 31, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$497
(Delta)

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.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-George Town Owen Roberts Intl flights.
Search Deals
From Oakland to Cayman Islands
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($112 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 31, 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

Fri 1/23

5:55 am-10:57 am

2 stops26h 02m

George Town Owen Roberts Intl

Mon 1/26

2:05 pm-11:52 am

2 stops24h 47m

$497

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Fri 1/23

12:33 pm-10:57 am

2 stops19h 24m

George Town Owen Roberts Intl

Tue 1/27

2:05 pm-11:53 pm

2 stops12h 48m

$567

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Thu 1/22

5:55 am-12:40 pm

2 stops27h 45m

George Town Owen Roberts Intl

Mon 1/26

2:05 pm-11:52 am

2 stops24h 47m

$567

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Thu 1/22

5:55 am-12:40 pm

2 stops27h 45m

George Town Owen Roberts Intl

Tue 1/27

2:05 pm-11:53 pm

2 stops12h 48m

$637

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Fri 2/6

5:55 am-11:19 am

2 stops26h 24m

George Town Owen Roberts Intl

Sun 2/8

2:05 pm-11:52 am

2 stops24h 47m

$684

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Thu 2/5

12:33 pm-12:40 pm

2 stops21h 07m

George Town Owen Roberts Intl

Sun 2/8

2:05 pm-11:52 am

2 stops24h 47m

$684

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 1/24

12:33 pm-12:40 pm

2 stops21h 07m

George Town Owen Roberts Intl

Tue 1/27

2:05 pm-11:53 pm

2 stops12h 48m

$697

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Mon 4/13

5:55 am-11:24 am

2 stops27h 29m

George Town Owen Roberts Intl

Mon 4/20

12:45 pm-11:49 pm

2 stops37h 04m

$725

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Tue 4/14

5:55 am-11:24 am

2 stops27h 29m

George Town Owen Roberts Intl

Mon 4/20

12:45 pm-11:49 pm

2 stops37h 04m

$725

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Fri 2/6

5:55 am-11:19 am

2 stops26h 24m

George Town Owen Roberts Intl

Mon 2/9

2:05 pm-4:14 pm

2 stops29h 09m

$725

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 12 results
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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 $409). 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 26h 02m. Fly via Delta 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.

  • 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 $409). 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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