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$180+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
ago. 23 — ago. 301
sáb. 8/23
sáb. 8/30
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 agosto 18, 2025.

Round-trip from

$365
(FlightHub)

One-way from

$180
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$524
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. 9% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 18, 2025.

This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/812:15 pmOAK - SJU
2 stops28h 29mSpirit Airlines
lun. 11/106:00 amSJU - OAK
2 stops14h 15mSpirit Airlines
Deal found 8/17$365
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/612:15 pmOAK - SJU
2 stops24h 08mSpirit Airlines
lun. 11/106:00 amSJU - OAK
2 stops14h 15mSpirit Airlines
Deal found 8/17$371
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/45:11 pmOAK - SJU
2 stops15h 49mSpirit Airlines
lun. 12/86:00 amSJU - OAK
2 stops38h 16mSpirit Airlines
Deal found 8/16$377
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/12:39 pmOAK - STT
2 stops16h 05mSpirit Airlines
vie. 10/1711:01 amSTT - OAK
2 stops23h 48mSpirit Airlines
Deal found 8/17$382
This Priceline deal was found by Cheapflights users on 8/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/272:39 pmOAK - STT
2 stops16h 05mSpirit Airlines
sáb. 10/410:49 amSTT - OAK
2 stops15h 43mSpirit Airlines
Deal found 8/16$384
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:26 pmOAK - SJU
2 stops47h 18mSpirit Airlines
lun. 11/106:00 amSJU - OAK
2 stops14h 15mSpirit Airlines
Deal found 8/17$388
This Southwest deal was found by Cheapflights users on 8/17. 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.
mar. 9/167:10 pmOAK - SJU
2 stops12h 40mSouthwest
mar. 9/237:20 amSJU - OAK
2 stops13h 20mSouthwest
Deal found 8/17$390
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/272:39 pmOAK - STT
2 stops16h 05mSpirit Airlines
vie. 10/310:49 amSTT - OAK
2 stops15h 43mSpirit Airlines
Deal found 8/16$396
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/612:15 pmOAK - SJU
2 stops24h 08mSpirit Airlines
dom. 11/99:49 pmSJU - OAK
2 stops41h 21mSpirit Airlines
Deal found 8/17$407
This Mytrip deal was found by Cheapflights users on 8/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/316:00 amOAK - SJU
2 stops24h 05mSpirit Airlines
jue. 9/43:22 pmSJU - OAK
3 stops35h 10mSpirit Airlines
Deal found 8/16$412
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/102:39 pmOAK - STT
2 stops16h 05mSpirit Airlines
mar. 9/1610:49 amSTT - OAK
2 stops15h 43mSpirit Airlines
Deal found 8/17$415
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/112:39 pmOAK - STT
2 stops16h 05mSpirit Airlines
vie. 9/1910:49 amSTT - OAK
2 stops15h 43mSpirit Airlines
Deal found 8/17$421

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 agosto 18, 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

sáb. 11/8

12:15 pm-8:44 pm

2 stops28h 29m

San Juan Luis Munoz Marin Intl

lun. 11/10

6:00 am-4:15 pm

2 stops14h 15m

$365

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

jue. 11/6

12:15 pm-4:23 pm

2 stops24h 08m

San Juan Luis Munoz Marin Intl

lun. 11/10

6:00 am-4:15 pm

2 stops14h 15m

$371

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

jue. 12/4

5:11 pm-1:00 pm

2 stops15h 49m

San Juan Luis Munoz Marin Intl

lun. 12/8

6:00 am-4:16 pm

2 stops38h 16m

$377

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

mié. 10/1

2:39 pm-9:44 am

2 stops16h 05m

Saint Thomas Island Cyril E King

vie. 10/17

11:01 am-7:49 am

2 stops23h 48m

$382

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

sáb. 9/27

2:39 pm-9:44 am

2 stops16h 05m

Saint Thomas Island Cyril E King

sáb. 10/4

10:49 am-11:32 pm

2 stops15h 43m

$384

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

vie. 11/7

5:26 pm-8:44 pm

2 stops47h 18m

San Juan Luis Munoz Marin Intl

lun. 11/10

6:00 am-4:15 pm

2 stops14h 15m

$388

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

mar. 9/16

7:10 pm-10:50 am

2 stops12h 40m

San Juan Luis Munoz Marin Intl

mar. 9/23

7:20 am-5:40 pm

2 stops13h 20m

$390

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

sáb. 9/27

2:39 pm-9:44 am

2 stops16h 05m

Saint Thomas Island Cyril E King

vie. 10/3

10:49 am-11:32 pm

2 stops15h 43m

$396

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

jue. 12/4

7:10 pm-10:25 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

mar. 12/9

5:45 am-2:05 pm

2 stops12h 20m

$407

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

jue. 11/6

12:15 pm-4:23 pm

2 stops24h 08m

San Juan Luis Munoz Marin Intl

dom. 11/9

9:49 pm-11:10 am

2 stops41h 21m

$407

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 59 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 agosto 18, 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 agosto 18, 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
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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
8,038 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

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 14h 35m. Spirit Airlines provides one of the quickest options available for as low as $604. Airlines will cover a distance of 3640 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 Spirit Airlines. According to our data, you can fly for as low as $180. Users have also found prices from $230 and $256 on Delta and Southwest, 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 - Saint Thomas Island Cyril E King or Oakland - Punta Cana 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 agosto 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$260Average$419FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$683FlexibilityNo cancel feeOn-time63%

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