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$177+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
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 October 31, 2025.

Round-trip from

$355
(Southwest)

One-way from

$177
(Delta)

Popular in

December

Cheapest in

May

Average price

$443
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 ($51 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 October 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 October 31, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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 12/154:50 pmOAK - NAS
2 stops19h 53mDelta
Wed 12/242:27 pmNAS - OAK
2 stops24h 27mDelta
Deal found 10/29$465
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/1612:30 pmOAK - NAS
2 stops22h 00mDelta
Wed 12/2412:33 pmNAS - OAK
2 stops26h 21mDelta
Deal found 10/29$526
This Southwest deal was found by Cheapflights users on 10/30. 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 11/273:30 pmOAK - PUJ
2 stops19h 30mSouthwest
Wed 12/102:40 pmPUJ - OAK
2 stops20h 50mSouthwest
Deal found 10/30$575
This Delta deal was found by Cheapflights users on 10/28. 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 12/1312:30 pmOAK - PUJ
2 stops20h 43mDelta
Sat 12/204:46 pmPUJ - OAK
2 stops23h 08mDelta
Deal found 10/28$596
This Southwest deal was found by Cheapflights users on 10/27. 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 12/108:20 amOAK - SJU
2 stops12h 15mSouthwest
Thu 1/15:45 amSJU - OAK
2 stops12h 20mSouthwest
Deal found 10/27$635
This Southwest deal was found by Cheapflights users on 10/29. 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 12/128:55 pmOAK - MBJ
2 stops14h 40mSouthwest
Fri 12/193:25 pmMBJ - OAK
2 stops12h 00mSouthwest
Deal found 10/29$640
This Delta deal was found by Cheapflights users on 10/30. 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 11/2712:28 pmOAK - PUJ
2 stops20h 45mDelta
Wed 12/102:38 pmPUJ - OAK
2 stops13h 30mDelta
Deal found 10/30$686
This Delta deal was found by Cheapflights users on 10/29. 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 12/154:50 pmOAK - NAS
2 stops19h 53mDelta
Thu 12/251:31 pmNAS - OAK
2 stops12h 16mDelta
Deal found 10/29$699
This Delta deal was found by Cheapflights users on 10/29. 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 12/154:50 pmOAK - NAS
2 stops19h 53mDelta
Fri 12/268:10 amNAS - OAK
2 stops18h 48mDelta
Deal found 10/29$753
This Delta deal was found by Cheapflights users on 10/29. 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 11/2612:28 pmOAK - AUA
2 stops22h 52mDelta
Wed 12/34:35 pmAUA - OAK
2 stops27h 29mDelta
Deal found 10/29$778
This Delta deal was found by Cheapflights users on 10/29. 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 12/154:50 pmOAK - NAS
2 stops19h 53mDelta
Mon 12/228:10 amNAS - OAK
2 stops18h 48mDelta
Deal found 10/29$778
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Thu 11/2711:17 pmOAK - PUJ
2 stops18h 38mMultiple Airlines
Wed 12/106:36 pmPUJ - OAK
3 stops30h 54mMultiple Airlines
Deal found 10/30$808

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 October 31, 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

Tue 1/27

7:25 pm-11:20 am

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Mon 2/2

12:10 pm-9:25 pm

2 stops13h 15m

$355

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 1/28

9:40 am-12:35 am

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Mon 2/2

12:10 pm-9:25 pm

2 stops13h 15m

$355

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 12/16

12:30 pm-1:30 pm

2 stops22h 00m

Nassau Intl

Wed 12/24

12:33 pm-11:54 am

2 stops26h 21m

$526

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 3/24

5:55 am-10:10 am

2 stops26h 15m

Montego Bay Sangster Intl

Tue 3/31

8:00 am-11:53 pm

2 stops17h 53m

$570

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Thu 11/27

3:30 pm-3:00 pm

2 stops19h 30m

Punta Cana

Wed 12/10

2:40 pm-7:30 am

2 stops20h 50m

$575

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sat 12/13

12:30 pm-1:13 pm

2 stops20h 43m

Punta Cana

Sat 12/20

4:46 pm-11:54 am

2 stops23h 08m

$596

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Sun 3/15

5:55 am-11:55 am

2 stops27h 00m

Oranjestad Reina Beatrix

Tue 3/17

1:10 pm-11:53 pm

2 stops13h 43m

$614

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Mon 3/9

1:15 pm-2:10 pm

2 stops21h 55m

Oranjestad Reina Beatrix

Tue 3/17

3:25 pm-12:30 pm

2 stops24h 05m

$614

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Sat 3/14

1:15 pm-11:30 am

2 stops19h 15m

Oranjestad Reina Beatrix

Tue 3/17

3:25 pm-12:30 pm

2 stops24h 05m

$614

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 12/12

8:55 pm-2:35 pm

2 stops14h 40m

Montego Bay Sangster Intl

Fri 12/19

3:25 pm-12:25 am

2 stops12h 00m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 October 31, 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 October 31, 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
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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 11h 55m. 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 - Kingston Norman Manley 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 October 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$278Average$534FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$560FlexibilityNo cancel feeOn-time63%

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