HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$203+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 21, 2025.

This Delta deal was found by Cheapflights users on 12/21. 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 12/285:53 amOAK - PUJ
2 stops26h 48mDelta
Wed 12/314:46 pmPUJ - OAK
2 stops34h 01mDelta
Deal found 12/21$792
This Southwest deal was found by Cheapflights users on 12/19. 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.
Fri 12/2611:00 amOAK - SJU
2 stops10h 40mSouthwest
Fri 1/166:10 amSJU - OAK
2 stops19h 15mSouthwest
Deal found 12/19$840
This Delta deal was found by Cheapflights users on 12/21. 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 12/285:53 amOAK - PUJ
2 stops29h 28mDelta
Tue 12/304:46 pmPUJ - OAK
2 stops34h 01mDelta
Deal found 12/21$840
This Delta deal was found by Cheapflights users on 12/21. 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 12/2412:34 pmOAK - PUJ
2 stops20h 07mDelta
Mon 12/296:03 pmPUJ - OAK
2 stops21h 51mDelta
Deal found 12/21$870
This Delta deal was found by Cheapflights users on 12/21. 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 12/224:50 pmOAK - PUJ
2 stops18h 31mDelta
Wed 12/316:03 pmPUJ - OAK
2 stops32h 44mDelta
Deal found 12/21$872
This Delta deal was found by Cheapflights users on 12/21. 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 12/2412:34 pmOAK - PUJ
2 stops22h 47mDelta
Tue 12/304:46 pmPUJ - OAK
2 stops34h 01mDelta
Deal found 12/21$918
This Delta deal was found by Cheapflights users on 12/21. 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 12/224:50 pmOAK - PUJ
2 stops18h 31mDelta
Tue 12/304:46 pmPUJ - OAK
2 stops34h 01mDelta
Deal found 12/21$921
This Southwest deal was found by Cheapflights users on 12/20. 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.
Wed 12/245:40 amOAK - SJU
2 stops14h 55mSouthwest
Wed 12/3111:20 amSJU - OAK
2 stops13h 15mSouthwest
Deal found 12/20$951
This Southwest deal was found by Cheapflights users on 12/20. 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.
Wed 12/246:30 pmOAK - PUJ
2 stops16h 30mSouthwest
Fri 12/264:00 pmPUJ - OAK
2 stops12h 25mSouthwest
Deal found 12/20$985
This Delta deal was found by Cheapflights users on 12/21. 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 12/265:53 amOAK - PUJ
2 stops26h 48mDelta
Mon 12/296:03 pmPUJ - OAK
2 stops26h 01mDelta
Deal found 12/21$999
This Delta deal was found by Cheapflights users on 12/21. 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 12/275:53 amOAK - PUJ
2 stops28h 20mDelta
Mon 12/296:03 pmPUJ - OAK
2 stops26h 01mDelta
Deal found 12/21$1,031
This Delta deal was found by Cheapflights users on 12/21. 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 12/265:53 amOAK - PUJ
2 stops26h 48mDelta
Tue 12/304:46 pmPUJ - OAK
2 stops34h 01mDelta
Deal found 12/21$1,047

Find flight deals from Oakland to Caribbean

Keep the following information in mind while searching for Oakland to Caribbean flight deals. Data was last updated December 21, 2025.

Round-trip from

$382
(Southwest)

One-way from

$203
(Southwest)

Popular in

December

Cheapest in

May

Average price

$601
From Oakland to Caribbean
Search Deals
One-way flight from Oakland to Caribbean
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 21, 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

Wed 4/15

7:35 pm-9:10 am

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Fri 4/24

2:00 pm-10:30 pm

2 stops11h 30m

$382

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 1/7

9:40 am-12:35 am

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Tue 1/13

5:40 am-2:55 pm

2 stops13h 15m

$491

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 2/19

9:10 am-12:40 am

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Thu 2/26

3:15 pm-12:10 am

2 stops12h 55m

$491

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 1/13

7:25 am-12:35 am

2 stops13h 10m

San Juan Luis Munoz Marin Intl

Mon 1/26

12:10 pm-9:45 pm

2 stops13h 35m

$547

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Mon 2/2

5:00 pm-2:20 pm

2 stops17h 20m

Punta Cana

Mon 2/9

2:55 pm-4:14 pm

2 stops29h 19m

$563

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 3/3

5:25 pm-1:00 pm

2 stops16h 35m

Nassau Intl

Wed 4/1

8:45 am-7:50 pm

2 stops14h 05m

$576

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Thu 5/28

8:55 pm-1:15 pm

2 stops13h 20m

Nassau Intl

Sun 5/31

2:15 pm-11:35 pm

2 stops12h 20m

$615

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 5/30

7:55 pm-1:20 pm

2 stops14h 25m

Nassau Intl

Sat 6/6

2:20 pm-11:20 pm

2 stops12h 00m

$615

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 3/28

7:35 pm-12:05 pm

2 stops13h 30m

Nassau Intl

Sat 4/4

8:35 am-8:20 pm

2 stops14h 45m

$615

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 1/3

12:34 pm-11:08 am

2 stops19h 34m

Nassau Intl

Wed 1/7

1:41 pm-10:53 pm

2 stops12h 12m

$623

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 47 results
1
2
3
...
5

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 December 21, 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 13% 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 December 21, 2025.
Get a feel of what it's like to fly with Southwest 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
4,254 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 35m. Southwest provides one of the quickest options available for as low as $382. 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 - Punta Cana or Oakland - Saint Thomas Island Cyril E King 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
Los Angeles to Haneda flights
San Francisco to Las Vegas flights
Los Angeles to Newark flights
San Francisco to John F Kennedy Intl flights
Los Angeles to Narita flights
Los Angeles to Seattle flights
Los Angeles to LaGuardia flights
Los Angeles to Mexico City flights
Los Angeles to Honolulu flights
San Francisco to Haneda flights
Los Angeles to Miami flights
Los Angeles to Las Vegas flights
Los Angeles to Cancún flights
San Francisco to Honolulu flights
Los Angeles to Dallas/Fort Worth flights
San Francisco to Newark flights
Los Angeles to Orlando flights
Los Angeles to San Francisco flights
Los Angeles to O'Hare Intl flights
San Francisco to Dallas/Fort Worth flights
San Francisco to Cancún flights
Santa Ana to Las Vegas flights
Burbank to Las Vegas flights
Los Angeles to Manila flights
Los Angeles to Fort Lauderdale flights
San Francisco to Narita flights
Ontario to San Francisco flights
San Jose to Las Vegas flights
San Francisco to Mexico City flights
San Francisco to Los Angeles flights
San Francisco to LaGuardia flights
Los Angeles to Suvarnabhumi flights
San Francisco to Ontario flights
San Francisco to New Delhi flights
Los Angeles to Salt Lake City flights
Los Angeles to Heathrow flights
Los Angeles to Boston flights
San Francisco to Miami flights
Los Angeles to Denver flights
San Francisco to Manila flights
San Francisco to Kahului flights
Ontario to Seattle flights
Oakland to Las Vegas flights
San Francisco to Seattle flights
Los Angeles to Charles de Gaulle flights
Los Angeles to Kahului flights
Los Angeles to San Salvador flights
San Francisco to Heathrow flights
Los Angeles to San José del Cabo flights

Top airline flying from Oakland to Caribbean

Discover the top airline 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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$385Average$574FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.