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Caribbean Islands

$198+ Cheap flights from Oakland, CA (OAK) to Caribbean Islands

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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean Islands

Cheapest flights from Oakland to Caribbean Islands
Explore the most affordable flight options available from Oakland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 1, 2026.

This Southwest deal was found by Cheapflights users on 12/30. 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 12/307:25 pmOAK - SJU
2 stops11h 00mSouthwest
Tue 1/65:40 amSJU - OAK
2 stops13h 15mSouthwest
Deal found 12/30$871
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/315:53 amOAK - SJU
2 stops16h 34mDelta
Sun 1/116:15 amSJU - OAK
2 stops20h 38mDelta
Deal found 12/30$1,323
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/315:53 amOAK - SJU
2 stops14h 06mDelta
Tue 1/67:30 amSJU - OAK
2 stops19h 23mDelta
Deal found 12/30$1,605
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/315:53 amOAK - SJU
2 stops14h 06mDelta
Wed 1/77:30 amSJU - OAK
2 stops19h 23mDelta
Deal found 12/30$1,655

Find flight deals from Oakland to Caribbean Islands

Keep the following information in mind while searching for Oakland to Caribbean Islands flight deals. Data was last updated January 1, 2026.

Round-trip from

$413
(Southwest)

One-way from

$198
(Southwest)

Popular in

December

Cheapest in

May

Average price

$442
From Oakland to Caribbean Islands
Search Deals
One-way flight from Oakland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Caribbean 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 January 1, 2026.
Use the filters below to find and compare flights from Oakland to Caribbean Islands that are best for you.

Fly from

Oakland

Fly to

Caribbean Islands

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 3/3

8:10 am-12:35 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

Sat 3/7

7:00 am-4:35 pm

2 stops13h 35m

$413

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 1/23

12:33 pm-12:43 pm

2 stops20h 10m

Punta Cana

Thu 1/29

5:35 pm-11:52 am

2 stops22h 17m

$500

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sat 1/24

12:33 pm-1:07 pm

2 stops20h 34m

Punta Cana

Thu 1/29

5:35 pm-4:14 pm

2 stops26h 39m

$500

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Wed 1/28

12:33 pm-4:09 pm

2 stops23h 36m

Punta Cana

Tue 2/3

3:45 pm-11:52 am

2 stops24h 07m

$500

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 1/25

12:33 pm-1:07 pm

2 stops20h 34m

Punta Cana

Thu 1/29

5:35 pm-11:52 am

2 stops22h 17m

$500

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 1/17

12:38 pm-5:00 pm

2 stops25h 22m

Nassau Intl

Mon 2/2

2:56 pm-11:53 pm

2 stops11h 57m

$544

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 1/17

12:38 pm-5:00 pm

2 stops25h 22m

Nassau Intl

Tue 2/3

2:56 pm-11:53 pm

2 stops11h 57m

$544

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Mon 1/12

4:54 pm-1:31 pm

2 stops17h 37m

Nassau Intl

Tue 2/3

2:56 pm-11:52 am

2 stops23h 56m

$544

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 1/13

5:55 am-1:31 pm

2 stops28h 36m

Nassau Intl

Mon 2/2

2:56 pm-11:53 pm

2 stops11h 57m

$544

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 1/13

12:38 pm-1:31 pm

2 stops21h 53m

Nassau Intl

Tue 2/3

2:56 pm-11:52 am

2 stops23h 56m

$544

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 49 results
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Best time to book a flight from Oakland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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 Caribbean Islands

What is the cheapest month to book a flight from Oakland, California to Caribbean Islands?

Currently, December is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $169). Flying from Oakland, California to Caribbean Islands in June is currently the most expensive (average of $296). 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 Caribbean 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 Caribbean Islands?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Caribbean Islands.

  • How long is the flight from Oakland, California to Caribbean Islands?

    Southwest, Delta, and Alaska Airlines can get you from Oakland, California to Caribbean Islands in just under 12h 25m. Your travel time can differ by up to 14h 29m. The distance from Oakland, California to Caribbean Islands is about 3615 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Oakland, California to Caribbean Islands?

    The most popular route from Oakland, California to Caribbean Islands is Oakland - San Juan Luis Munoz Marin Intl. You may also consider Oakland - Punta Cana or Oakland - Nassau Intl.

  • Can I find deals for flights from Oakland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Oakland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Caribbean Islands.

  • Can I find deals for business class flights from Oakland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Oakland to Caribbean 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 Caribbean Islands?

    Currently, December is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $169). Flying from Oakland, California to Caribbean Islands in June is currently the most expensive (average of $296). 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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Top airline flying from Oakland to Caribbean Islands

Discover the top airline that operate flights from Oakland to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$385Average$574FlexibilityNo cancel feeOn-time63%

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