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$261+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 20, 2025.

Round-trip from

$481
(Southwest)

One-way from

$261
(Southwest)

Popular in

December

Cheapest in

May

Average price

$509
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. 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

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 20, 2025.

This Delta deal was found by Cheapflights users on 11/20. 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 12/134:50 pmOAK - NAS
2 stops17h 40mDelta
Mon 12/152:55 pmNAS - OAK
2 stops12h 13mDelta
Deal found 11/20$544
This Southwest deal was found by Cheapflights users on 11/20. 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 12/59:50 amOAK - SJU
2 stops10h 45mSouthwest
Mon 12/88:55 amSJU - OAK
2 stops13h 15mSouthwest
Deal found 11/20$551
This Delta deal was found by Cheapflights users on 11/20. 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 12/1212:30 pmOAK - NAS
2 stops22h 00mDelta
Mon 12/155:08 pmNAS - OAK
2 stops21h 42mDelta
Deal found 11/20$623
This Delta deal was found by Cheapflights users on 11/20. 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 12/54:50 pmOAK - NAS
2 stops17h 40mDelta
Mon 12/81:19 pmNAS - OAK
2 stops13h 49mDelta
Deal found 11/20$671
This Delta deal was found by Cheapflights users on 11/20. 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 12/65:55 amOAK - NAS
2 stops26h 59mDelta
Mon 12/81:19 pmNAS - OAK
2 stops13h 49mDelta
Deal found 11/20$719
This Delta deal was found by Cheapflights users on 11/17. 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 12/812:30 pmOAK - MBJ
2 stops21h 34mDelta
Fri 12/122:29 pmMBJ - OAK
2 stops24h 21mDelta
Deal found 11/17$726
This Southwest deal was found by Cheapflights users on 11/19. 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 11/235:25 amOAK - SJU
2 stops12h 55mSouthwest
Thu 11/275:45 amSJU - OAK
2 stops14h 45mSouthwest
Deal found 11/19$773
This Southwest deal was found by Cheapflights users on 11/18. 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 11/246:05 pmOAK - SJU
2 stops12h 40mSouthwest
Fri 11/285:40 amSJU - OAK
2 stops12h 55mSouthwest
Deal found 11/18$795
This Delta deal was found by Cheapflights users on 11/17. 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.
Thu 12/412:30 pmOAK - MBJ
2 stops22h 43mDelta
Fri 12/122:29 pmMBJ - OAK
2 stops24h 21mDelta
Deal found 11/17$805
This Delta deal was found by Cheapflights users on 11/20. 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 12/1212:30 pmOAK - NAS
2 stops22h 00mDelta
Sun 12/142:55 pmNAS - OAK
2 stops12h 13mDelta
Deal found 11/20$851
This Delta deal was found by Cheapflights users on 11/20. 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 12/55:55 amOAK - NAS
2 stops28h 35mDelta
Sun 12/72:55 pmNAS - OAK
2 stops36h 13mDelta
Deal found 11/20$857
This Delta deal was found by Cheapflights users on 11/19. 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 12/512:30 pmOAK - MBJ
2 stops21h 24mDelta
Fri 12/122:29 pmMBJ - OAK
2 stops34h 31mDelta
Deal found 11/19$863

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 20, 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

Fri 2/27

7:50 pm-10:00 am

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Sat 3/7

7:00 am-4:40 pm

2 stops13h 40m

$481

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sat 1/24

7:30 pm-1:40 pm

2 stops14h 10m

Punta Cana

Sat 1/31

3:00 pm-10:35 pm

1 stop11h 35m

$516

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 12/13

4:50 pm-1:30 pm

2 stops17h 40m

Nassau Intl

Mon 12/15

2:55 pm-12:08 am

2 stops12h 13m

$544

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 12/5

9:50 am-12:35 am

2 stops10h 45m

San Juan Luis Munoz Marin Intl

Mon 12/8

8:55 am-6:10 pm

2 stops13h 15m

$551

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sun 1/11

12:38 pm-12:26 pm

2 stops20h 48m

Nassau Intl

Thu 1/15

1:15 pm-10:53 pm

2 stops12h 38m

$592

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Sun 2/15

5:55 am-12:40 pm

2 stops27h 45m

Providenciales

Tue 2/24

2:05 pm-11:57 am

2 stops24h 52m

$635

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Sun 2/15

5:55 am-12:40 pm

2 stops27h 45m

Providenciales

Mon 2/23

3:52 pm-11:57 am

2 stops23h 05m

$635

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Fri 12/5

4:50 pm-1:30 pm

2 stops17h 40m

Nassau Intl

Mon 12/8

1:19 pm-12:08 am

2 stops13h 49m

$671

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 12/6

5:55 am-11:54 am

2 stops26h 59m

Nassau Intl

Mon 12/8

1:19 pm-12:08 am

2 stops13h 49m

$719

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 1/1

8:20 am-12:25 am

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Thu 1/8

5:40 am-2:55 pm

2 stops13h 15m

$720

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 53 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 20, 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 14% 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 20, 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
4,249 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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
8,156 reviews
Southwest
8.0
Very good
4,249 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

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 10h 10m. Southwest provides one of the quickest options available for as low as $481. 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 cheapest airlines to fly from Oakland, California to Caribbean one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $261. Users have also found prices from $379 and $413 on Alaska Airlines and Delta, respectively.

  • 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 - Nassau Intl 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

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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$278Average$534FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$548FlexibilityNo cancel feeOn-time63%

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