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$236+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Round-trip from

$355
(Southwest)

One-way from

$236
(Delta)

Popular in

December

Cheapest in

May

Average price

$551
From Oakland to Caribbean
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One-way flight from Oakland to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 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

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 November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/4. 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 11/136:00 amOAK - SJU
2 stops12h 20mSouthwest
Thu 11/208:55 amSJU - OAK
2 stops13h 15mSouthwest
Deal found 11/4$462
This Southwest deal was found by Cheapflights users on 11/4. 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 12/47:10 pmOAK - SJU
2 stops11h 15mSouthwest
Sat 12/135:40 amSJU - OAK
2 stops12h 45mSouthwest
Deal found 11/4$474
This Southwest deal was found by Cheapflights users on 11/5. 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 12/119:00 amOAK - SJU
2 stops11h 35mSouthwest
Sun 12/145:40 amSJU - OAK
2 stops12h 55mSouthwest
Deal found 11/5$489
This Southwest deal was found by Cheapflights users on 11/5. 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 11/87:40 amOAK - SJU
2 stops12h 50mSouthwest
Sat 11/155:40 amSJU - OAK
2 stops12h 45mSouthwest
Deal found 11/5$509
This Southwest deal was found by Cheapflights users on 11/5. 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 12/217:15 pmOAK - PLS
2 stops15h 30mSouthwest
Fri 12/262:40 pmPLS - OAK
2 stops12h 45mSouthwest
Deal found 11/5$765
This Southwest deal was found by Cheapflights users on 11/5. 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 12/208:25 pmOAK - PLS
2 stops14h 20mSouthwest
Fri 12/262:40 pmPLS - OAK
2 stops20h 10mSouthwest
Deal found 11/5$775
This Southwest deal was found by Cheapflights users on 11/5. 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 12/217:15 pmOAK - PLS
2 stops15h 30mSouthwest
Thu 12/252:40 pmPLS - OAK
2 stops20h 10mSouthwest
Deal found 11/5$780
This Southwest deal was found by Cheapflights users on 11/6. 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 12/239:20 pmOAK - PUJ
2 stops13h 40mSouthwest
Mon 12/294:10 pmPUJ - OAK
2 stops18h 55mSouthwest
Deal found 11/6$881
This Mytrip deal was found by Cheapflights users on 11/5. 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.
Sun 11/2310:15 pmOAK - SDQ
2 stops12h 50mMultiple Airlines
Fri 11/287:49 pmSDQ - OAK
2 stops19h 56mMultiple Airlines
Deal found 11/5$891
This Delta deal was found by Cheapflights users on 11/6. 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 11/85:00 pmOAK - MBJ
2 stops16h 23mDelta
Thu 11/132:17 pmMBJ - OAK
2 stops12h 46mDelta
Deal found 11/6$919
This Delta deal was found by Cheapflights users on 11/3. 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 11/74:51 pmOAK - PUJ
2 stops15h 49mDelta
Thu 11/132:38 pmPUJ - OAK
2 stops13h 25mDelta
Deal found 11/3$934
This Delta deal was found by Cheapflights users on 11/6. 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 11/85:00 pmOAK - MBJ
2 stops16h 23mDelta
Wed 11/122:17 pmMBJ - OAK
2 stops12h 46mDelta
Deal found 11/6$956

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 November 6, 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

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 1/26

6:15 am-8:55 pm

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Sat 1/31

9:50 am-7:20 pm

2 stops13h 30m

$355

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 12/4

7:10 pm-10:25 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Fri 12/12

3:30 pm-12:10 am

2 stops12h 40m

$474

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 12/11

9:00 am-12:35 am

2 stops11h 35m

San Juan Luis Munoz Marin Intl

Sun 12/14

5:40 am-2:35 pm

2 stops12h 55m

$489

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sun 1/25

12:38 pm-3:30 pm

2 stops22h 52m

Punta Cana

Fri 1/30

5:46 pm-11:57 am

2 stops22h 11m

$500

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Mon 1/26

4:54 pm-2:20 pm

2 stops17h 26m

Punta Cana

Fri 1/30

5:46 pm-9:38 pm

2 stops31h 52m

$500

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 12/1

11:00 am-1:40 am

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Mon 12/8

11:20 am-7:50 pm

2 stops12h 30m

$509

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 5/1

11:55 pm-3:00 pm

1 stop12h 05m

Punta Cana

Fri 5/8

1:40 pm-7:50 am

2 stops21h 10m

$540

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 1/30

12:38 pm-12:43 pm

2 stops20h 05m

Punta Cana

Tue 2/3

2:55 pm-11:57 am

2 stops25h 02m

$578

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 3/3

5:55 am-11:10 am

2 stops26h 15m

Montego Bay Sangster Intl

Thu 3/5

12:35 pm-11:57 am

2 stops26h 22m

$638

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Fri 5/1

1:15 pm-2:30 pm

2 stops22h 15m

Providenciales

Fri 5/8

2:00 pm-11:49 pm

2 stops12h 49m

$677

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 60 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, December is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $169). Flying from Oakland, California to Caribbean 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 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 November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Oakland, California to Caribbean in the morning. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the afternoon.

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 November 6, 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
4,240 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

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
8,114 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

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 10h 40m. Southwest provides one of the quickest options available for as low as $355. 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 - Providenciales 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, December is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $169). Flying from Oakland, California to Caribbean 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

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$278Average$534FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$548FlexibilityNo cancel feeOn-time63%

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