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$208+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Mar 21 — Mar 281
Sat 3/21
Sat 3/28
1 adult, Economy
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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 February 19, 2026.

This Southwest deal was found by Cheapflights users on 2/18. 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.
Wed 6/1710:25 am
OAK
-
SJU
2 stops10h 50m
Southwest
Wed 6/246:30 am
SJU
-
OAK
1 stop10h 20m
Southwest
Deal found 2/18$411
This Southwest deal was found by Cheapflights users on 2/16. 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.
Wed 4/88:50 am
OAK
-
SJU
2 stops11h 50m
Southwest
Tue 4/148:10 am
SJU
-
OAK
2 stops13h 40m
Southwest
Deal found 2/16$416
This Southwest deal was found by Cheapflights users on 2/16. 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.
Wed 5/67:35 pm
OAK
-
SJU
2 stops10h 35m
Southwest
Wed 5/1311:25 am
SJU
-
OAK
2 stops13h 30m
Southwest
Deal found 2/16$417
This Southwest deal was found by Cheapflights users on 2/15. 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 6/57:40 pm
OAK
-
SJU
2 stops11h 50m
Southwest
Thu 6/115:00 am
SJU
-
OAK
2 stops11h 30m
Southwest
Deal found 2/15$438
This Southwest deal was found by Cheapflights users on 2/17. 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.
Mon 6/227:50 am
OAK
-
SJU
2 stops13h 35m
Southwest
Wed 7/16:30 am
SJU
-
OAK
1 stop10h 20m
Southwest
Deal found 2/17$451
This Southwest deal was found by Cheapflights users on 2/16. 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.
Mon 7/207:50 am
OAK
-
SJU
2 stops13h 35m
Southwest
Fri 8/145:00 am
SJU
-
OAK
2 stops11h 45m
Southwest
Deal found 2/16$456
This Southwest deal was found by Cheapflights users on 2/15. 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 6/57:40 pm
OAK
-
SJU
2 stops11h 50m
Southwest
Mon 6/810:20 pm
SJU
-
OAK
2 stops15h 05m
Southwest
Deal found 2/15$463
This Southwest deal was found by Cheapflights users on 2/17. 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 5/27:35 pm
OAK
-
SJU
2 stops10h 30m
Southwest
Sat 5/99:40 am
SJU
-
OAK
2 stops12h 20m
Southwest
Deal found 2/17$483
This Southwest deal was found by Cheapflights users on 2/16. 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.
Thu 7/27:50 am
OAK
-
SJU
2 stops13h 35m
Southwest
Wed 7/86:30 am
SJU
-
OAK
2 stops12h 30m
Southwest
Deal found 2/16$491
This Southwest deal was found by Cheapflights users on 2/16. 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 2/286:25 pm
OAK
-
SJU
2 stops11h 30m
Southwest
Wed 3/410:20 am
SJU
-
OAK
2 stops13h 30m
Southwest
Deal found 2/16$500
This Southwest deal was found by Cheapflights users on 2/16. 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 5/57:45 pm
OAK
-
MBJ
2 stops13h 30m
Southwest
Tue 5/1212:15 pm
MBJ
-
OAK
2 stops11h 50m
Southwest
Deal found 2/16$517
This Southwest deal was found by Cheapflights users on 2/16. 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.
Mon 5/117:30 pm
OAK
-
GCM
2 stops14h 40m
Southwest
Sun 5/1712:50 pm
GCM
-
OAK
2 stops13h 55m
Southwest
Deal found 2/16$520

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 February 19, 2026.

Round-trip from

$411
(Southwest)

One-way from

$208
(Southwest)

Popular in

December

Cheapest in

May

Average price

$499
From Oakland to Caribbean
Search Deals
One-way flight from Oakland to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 19, 2026.
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 6/17

10:25 am-12:15 am

2 stops10h 50m

San Juan Luis Munoz Marin Intl

Wed 6/24

6:30 am-1:50 pm

1 stop10h 20m

$411

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 5/6

7:35 pm-9:10 am

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Wed 5/13

11:25 am-9:55 pm

2 stops13h 30m

$417

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 6/5

7:40 pm-10:30 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Thu 6/11

5:00 am-1:30 pm

2 stops11h 30m

$438

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 6/5

7:40 pm-10:30 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Mon 6/8

10:20 pm-10:25 am

2 stops15h 05m

$463

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 6/22

5:10 am-12:15 am

2 stops16h 05m

San Juan Luis Munoz Marin Intl

Wed 7/1

6:30 am-3:40 pm

2 stops12h 10m

$476

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 7/7

6:05 am-12:45 am

2 stops15h 40m

San Juan Luis Munoz Marin Intl

Mon 7/13

10:20 pm-10:25 am

2 stops15h 05m

$476

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 3/1

10:35 am-1:35 am

2 stops11h 00m

San Juan Luis Munoz Marin Intl

Wed 3/4

10:20 am-7:50 pm

2 stops13h 30m

$500

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 6/4

7:50 am-12:25 am

2 stops13h 35m

San Juan Luis Munoz Marin Intl

Sun 6/7

2:00 pm-11:20 pm

2 stops12h 20m

$516

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 5/5

7:45 pm-11:15 am

2 stops13h 30m

Montego Bay Sangster Intl

Tue 5/12

12:15 pm-10:05 pm

2 stops11h 50m

$517

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Mon 5/11

7:30 pm-12:10 pm

2 stops14h 40m

George Town Owen Roberts Intl

Sun 5/17

12:50 pm-12:45 am

2 stops13h 55m

$520

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

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, January is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $162). 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.

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 February 19, 2026.
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
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

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 50m. Southwest provides one of the quickest options available for as low as $411. 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 - Montego Bay Sangster 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, January is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $162). 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 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 February 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$385Average$558FlexibilityNo cancel feeOn-time63%

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