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Grand Cayman

$780+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — GCM
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap 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 July 3, 2025.

Round-trip from

$780
(Southwest)

Popular in

December

Cheapest in

September

Average price

$728
From Oakland to Grand Cayman
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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.
Tue 7/227:05 pmOAK - GCM
2 stops14h 45mSouthwest
Sun 7/2712:45 pmGCM - OAK
2 stops23h 05mSouthwest
Deal found 7/1$780
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/226:00 amOAK - GCM
3 stops32h 10mMultiple Airlines
Sun 7/274:45 pmGCM - OAK
3 stops22h 58mMultiple Airlines
Deal found 7/1$810
This Delta deal was found by Cheapflights users on 7/2. 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 8/14:55 pmOAK - GCM
2 stops16h 47mDelta
Fri 8/812:37 pmGCM - OAK
2 stops13h 18mDelta
Deal found 7/2$1,163

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 July 3, 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

Tue 7/22

7:05 pm-11:50 am

2 stops14h 45m

George Town Owen Roberts Intl

Sun 7/27

12:45 pm-9:50 am

2 stops23h 05m

$780

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Tue 7/22

6:00 am-4:10 pm

3 stops32h 10m

George Town Owen Roberts Intl

Sun 7/27

4:45 pm-1:43 pm

3 stops22h 58m

$810

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Fri 8/1

4:55 pm-11:42 am

2 stops16h 47m

George Town Owen Roberts Intl

Fri 8/8

12:37 pm-11:55 pm

2 stops13h 18m

$1,163

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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, January is the cheapest month in which you can book a flight from Oakland, California to Grand Cayman (average of $467). Flying from Oakland, California to Grand Cayman in March is currently the most expensive (average of $594). 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.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Grand Cayman. Reviews last updated July 3, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta from Oakland to Grand Cayman to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

  • 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, January is the cheapest month in which you can book a flight from Oakland, California to Grand Cayman (average of $467). Flying from Oakland, California to Grand Cayman in March is currently the most expensive (average of $594). 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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