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Caribbean Islands

$194+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap 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 November 13, 2025.

Round-trip from

$432
(Southwest)

One-way from

$194
(Southwest)

Popular in

December

Cheapest in

May

Average price

$510
From Oakland to Caribbean Islands
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One-way flight from Oakland to Caribbean Islands
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Highest demand for flights based on searches. 5% potential increase in price ($30 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 November 2025
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Find 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 November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/12. 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.
Wed 12/38:20 amOAK - SJU
2 stops12h 15mSouthwest
Sat 12/135:40 amSJU - OAK
2 stops12h 45mSouthwest
Deal found 11/12$432
This Southwest deal was found by Cheapflights users on 11/11. 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 11/273:00 pmOAK - GCM
2 stops18h 45mSouthwest
Tue 12/21:30 pmGCM - OAK
2 stops11h 15mSouthwest
Deal found 11/11$659
This Delta deal was found by Cheapflights users on 11/12. 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 12/212:30 pmOAK - NAS
2 stops20h 24mDelta
Tue 12/92:55 pmNAS - OAK
2 stops12h 13mDelta
Deal found 11/12$669
This Delta deal was found by Cheapflights users on 11/11. 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.
Sun 11/235:55 amOAK - NAS
2 stops26h 59mDelta
Thu 11/272:55 pmNAS - OAK
2 stops23h 53mDelta
Deal found 11/11$719
This Delta deal was found by Cheapflights users on 11/12. 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 11/195:55 amOAK - PUJ
2 stops28h 30mDelta
Wed 11/265:03 pmPUJ - OAK
2 stops22h 45mDelta
Deal found 11/12$749
This Delta deal was found by Cheapflights users on 11/12. 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 12/112:28 pmOAK - MBJ
2 stops21h 36mDelta
Thu 12/42:29 pmMBJ - OAK
2 stops12h 39mDelta
Deal found 11/12$754
This Southwest deal was found by Cheapflights users on 11/11. 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.
Wed 12/247:10 pmOAK - SJU
2 stops11h 15mSouthwest
Tue 12/303:25 pmSJU - OAK
2 stops13h 00mSouthwest
Deal found 11/11$778
This Southwest deal was found by Cheapflights users on 11/11. 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.
Sun 11/236:00 amOAK - SJU
2 stops12h 20mSouthwest
Thu 11/275:45 amSJU - OAK
2 stops15h 10mSouthwest
Deal found 11/11$792
This Delta deal was found by Cheapflights users on 11/11. 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.
Sun 11/235:55 amOAK - GCM
2 stops27h 40mDelta
Thu 11/271:50 pmGCM - OAK
2 stops24h 58mDelta
Deal found 11/11$826
This Delta deal was found by Cheapflights users on 11/12. 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 11/205:55 amOAK - PUJ
2 stops28h 30mDelta
Wed 11/265:03 pmPUJ - OAK
2 stops22h 45mDelta
Deal found 11/12$830
This Delta deal was found by Cheapflights users on 11/11. 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 12/295:53 amOAK - GCM
2 stops27h 43mDelta
Mon 1/53:45 pmGCM - OAK
2 stops23h 12mDelta
Deal found 11/11$845
This Delta deal was found by Cheapflights users on 11/11. 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 11/225:55 amOAK - GCM
2 stops27h 40mDelta
Thu 11/271:50 pmGCM - OAK
2 stops24h 58mDelta
Deal found 11/11$865

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 November 13, 2025.
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

Wed 12/3

9:55 am-12:35 am

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Sat 12/13

5:40 am-2:25 pm

2 stops12h 45m

$432

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Mon 4/6

5:55 am-1:30 pm

2 stops28h 35m

Nassau Intl

Tue 4/14

3:03 pm-11:49 pm

2 stops11h 46m

$465

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 4/7

5:55 am-1:30 pm

2 stops28h 35m

Nassau Intl

Tue 4/14

3:03 pm-11:49 pm

2 stops11h 46m

$465

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Wed 4/8

5:55 am-1:30 pm

2 stops28h 35m

Nassau Intl

Tue 4/14

3:03 pm-11:49 pm

2 stops11h 46m

$465

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 3/1

4:54 pm-12:35 pm

2 stops16h 41m

George Town Owen Roberts Intl

Tue 3/3

2:00 pm-11:57 am

2 stops24h 57m

$497

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 3/6

8:30 pm-10:50 am

2 stops10h 20m

San Juan Luis Munoz Marin Intl

Wed 3/11

10:10 am-10:10 pm

2 stops15h 00m

$509

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Wed 1/28

8:30 pm-2:30 pm

2 stops14h 00m

Punta Cana

Sat 1/31

3:00 pm-10:35 pm

1 stop11h 35m

$520

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sun 4/5

1:15 pm-1:15 pm

2 stops21h 00m

Nassau Intl

Tue 4/14

3:03 pm-11:49 pm

2 stops11h 46m

$542

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Wed 4/8

5:55 am-1:30 pm

2 stops28h 35m

Nassau Intl

Mon 4/13

3:20 pm-4:31 pm

2 stops28h 11m

$592

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 4/7

5:55 am-1:30 pm

2 stops28h 35m

Nassau Intl

Mon 4/13

3:20 pm-12:24 pm

2 stops24h 04m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 56 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.

What is the cheapest time of day to fly from OAK to EPX?

Find hourly flight availability from Oakland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

When flying from Oakland, California to Caribbean Islands, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 15% versus a flight in the afternoon.

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 10h 40m. Your travel time can differ by up to 17h 55m. 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 cheapest airlines to fly from Oakland, California to Caribbean Islands one-way?

    The cheapest airlines for a one-way flight from Oakland, California to Caribbean Islands are Southwest ($194), Delta ($436), and Alaska Airlines ($538).

  • 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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Alternative routes for Oakland to Caribbean Islands

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Top 2 airlines flying from Oakland to Caribbean Islands

Discover the top 2 airlines 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$278Average$534FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$548FlexibilityNo cancel feeOn-time63%

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