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$197+ Cheap flights from Oakland, CA (OAK) to Caribbean

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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean

Keep the following information in mind while searching for Oakland to Caribbean flight deals. Data was last updated September 17, 2025.

Round-trip from

$503
(Delta)

One-way from

$197
(Delta)

Popular in

December

Cheapest in

January

Average price

$468
From Oakland to Caribbean
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One-way flight from Oakland to Caribbean
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Highest demand for flights based on searches. 6% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Oakland to Caribbean

Cheapest flights from Oakland to Caribbean
Explore the most affordable flight options available from Oakland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Delta deal was found by Cheapflights users on 9/16. 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 11/164:51 pmOAK - PLS
2 stops16h 54mDelta
Fri 11/212:10 pmPLS - OAK
2 stops12h 53mDelta
Deal found 9/16$522
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 9/206:25 pmOAK - SJU
2 stops12h 10mSouthwest
Fri 9/265:50 amSJU - OAK
2 stops15h 40mSouthwest
Deal found 9/16$529
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 11/145:25 amOAK - SJU
2 stops12h 55mSouthwest
Mon 11/175:45 amSJU - OAK
2 stops12h 55mSouthwest
Deal found 9/15$533
This Southwest deal was found by Cheapflights users on 9/15. 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 11/138:45 amOAK - SJU
2 stops11h 50mSouthwest
Mon 11/175:45 amSJU - OAK
2 stops12h 55mSouthwest
Deal found 9/15$537
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 9/298:15 pmOAK - SJU
2 stops11h 35mSouthwest
Mon 10/610:05 amSJU - OAK
2 stops13h 40mSouthwest
Deal found 9/15$551
This Southwest deal was found by Cheapflights users on 9/16. 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 10/145:20 amOAK - SJU
2 stops12h 25mSouthwest
Tue 10/215:05 amSJU - OAK
2 stops15h 00mSouthwest
Deal found 9/16$579
This Delta deal was found by Cheapflights users on 9/17. 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 12/245:53 amOAK - NAS
2 stops26h 16mDelta
Wed 12/313:56 pmNAS - OAK
2 stops22h 58mDelta
Deal found 9/17$584
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 11/16:30 amOAK - SJU
2 stops11h 40mSouthwest
Sun 11/95:40 amSJU - OAK
2 stops12h 55mSouthwest
Deal found 9/17$644
This Southwest deal was found by Cheapflights users on 9/15. 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 11/199:50 amOAK - SJU
2 stops10h 45mSouthwest
Sun 11/235:40 amSJU - OAK
2 stops12h 50mSouthwest
Deal found 9/15$656
This Delta deal was found by Cheapflights users on 9/17. 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 12/2212:34 pmOAK - NAS
2 stops19h 35mDelta
Wed 12/313:56 pmNAS - OAK
2 stops22h 58mDelta
Deal found 9/17$663
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 10/138:00 pmOAK - SJU
2 stops10h 55mSouthwest
Mon 10/205:00 amSJU - OAK
2 stops12h 40mSouthwest
Deal found 9/15$665
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/310:10 amOAK - SJU
2 stops10h 40mSouthwest
Sun 10/52:25 pmSJU - OAK
2 stops11h 35mSouthwest
Deal found 9/15$669

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Caribbean 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 September 17, 2025.
Use the filters below to find and compare flights from Oakland to Caribbean that are best for you.

Fly from

Oakland

Fly to

Caribbean

Route

Depart

Return

Price

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Sun 11/16

4:51 pm-12:45 pm

2 stops16h 54m

Providenciales

Fri 11/21

2:10 pm-12:03 am

2 stops12h 53m

$522

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Mon 11/17

4:51 pm-12:45 pm

2 stops16h 54m

Providenciales

Fri 11/21

2:10 pm-12:03 am

2 stops12h 53m

$522

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 11/13

8:45 am-12:35 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Mon 11/17

5:45 am-2:40 pm

2 stops12h 55m

$537

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 9/29

8:15 pm-10:50 am

2 stops11h 35m

San Juan Luis Munoz Marin Intl

Mon 10/6

10:05 am-8:45 pm

2 stops13h 40m

$551

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Wed 12/24

5:53 am-11:09 am

2 stops26h 16m

Nassau Intl

Wed 12/31

3:56 pm-11:54 am

2 stops22h 58m

$584

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 11/1

6:30 am-9:10 pm

2 stops11h 40m

San Juan Luis Munoz Marin Intl

Sun 11/9

5:40 am-2:35 pm

2 stops12h 55m

$644

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 11/19

9:50 am-12:35 am

2 stops10h 45m

San Juan Luis Munoz Marin Intl

Sun 11/23

5:40 am-2:30 pm

2 stops12h 50m

$656

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Mon 12/22

12:34 pm-11:09 am

2 stops19h 35m

Nassau Intl

Wed 12/31

3:56 pm-11:54 am

2 stops22h 58m

$663

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 10/13

8:00 pm-9:55 am

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Mon 10/20

5:00 am-2:40 pm

2 stops12h 40m

$665

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Tue 3/3

1:15 pm-12:40 pm

2 stops20h 25m

Providenciales

Thu 3/5

2:05 pm-11:53 pm

2 stops12h 48m

$720

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 54 results
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Best time to book a flight from Oakland to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $254). Flying from Oakland, California to Caribbean in June is currently the most expensive (average of $339). 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 CB?

Find hourly flight availability from Oakland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Caribbean as you normally would.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated September 17, 2025.
Get a feel of what it's like to fly with Southwest and Spirit Airlines from Oakland to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Caribbean. 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?

    Most people fly from Oakland (OAK) if they book a flight from Oakland to Caribbean. Oakland is conveniently located just 7.0 mi from Oakland’s city center.

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

    A quick flight from Oakland, California to Caribbean can take about 11h 50m. Delta provides one of the quickest options available for as low as $537. Airlines will cover a distance of 3615 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    When deciding which route to take from Oakland, California to Caribbean consider Oakland - San Juan Luis Munoz Marin Intl, Oakland - Montego Bay Sangster Intl or Oakland - Oranjestad Reina Beatrix as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $254). Flying from Oakland, California to Caribbean in June is currently the most expensive (average of $339). 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Oakland to Caribbean

Discover the top 2 airlines that operate flights from Oakland to Caribbean. 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$260Average$419FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$651FlexibilityNo cancel feeOn-time63%

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