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Grand Cayman

$498+ Cheap flights from Oakland, CA (OAK) to Grand Cayman

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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
Apr 27 — May 41
Mon 4/27
Mon 5/4
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 March 28, 2026.

This Southwest deal was found by Cheapflights users on 3/25. 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.
Thu 6/187:45 pm
OAK
-
GCM
2 stops14h 05m
Southwest
Sat 6/2711:30 am
GCM
-
OAK
2 stops13h 40m
Southwest
Deal found 3/25$802
This Delta deal was found by Cheapflights users on 3/24. 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 8/85:30 pm
OAK
-
GCM
2 stops16h 01m
Delta
Sat 8/1512:56 pm
GCM
-
OAK
2 stops12h 53m
Delta
Deal found 3/24$2,706

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 March 28, 2026.

Round-trip from

$802
(Southwest)

One-way from

$498
(Delta)

Popular in

December

Cheapest in

September

Average price

$693
From Oakland to Grand Cayman
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One-way flight from Oakland to Grand Cayman
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Highest demand for flights based on searches. 18% potential increase in price ($151 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($49 potential savings vs. average RT price).
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Average for round-trip flights in March 2026
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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 March 28, 2026.
Use the filters below to find and compare flights from Oakland to Grand Cayman 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

Thu 6/18

7:45 pm-11:50 am

2 stops14h 05m

George Town Owen Roberts Intl

Sat 6/27

11:30 am-11:10 pm

2 stops13h 40m

$802

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 8/8

5:30 pm-11:31 am

2 stops16h 01m

George Town Owen Roberts Intl

Sat 8/15

12:56 pm-11:49 pm

2 stops12h 53m

$2,706
Cheapest one-way
Quickest one-way

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sat 8/8

5:30 pm-11:31 am

2 stops16h 01m

$498

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Sorted by cheapest first

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 $405). Flying from Oakland, California to Grand Cayman in August is currently the most expensive (average of $545). 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 $802, Southwest can have you in Grand Cayman from Oakland, California in 14h 05m. 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 $405). Flying from Oakland, California to Grand Cayman in August is currently the most expensive (average of $545). 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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Alternative routes for Oakland to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
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