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Caribbean Islands

$177+ Cheap flights from Oakland, CA (OAK) to Caribbean Islands

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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean Islands

Keep the following information in mind while searching for Oakland to Caribbean Islands flight deals. Data was last updated September 25, 2025.

Round-trip from

$465
(Delta)

One-way from

$177
(Delta)

Popular in

December

Cheapest in

May

Average price

$468
From Oakland to Caribbean Islands
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One-way flight from Oakland to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Oakland to Caribbean Islands

Cheapest flights from Oakland to Caribbean Islands
Explore the most affordable flight options available from Oakland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2025.

This Delta deal was found by Cheapflights users on 9/25. 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 11/85:00 pmOAK - NAS
2 stops15h 54mDelta
Tue 11/111:19 pmNAS - OAK
2 stops13h 44mDelta
Deal found 9/25$465
This Delta deal was found by Cheapflights users on 9/24. 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 11/85:00 pmOAK - MBJ
2 stops18h 11mDelta
Sat 11/154:05 pmMBJ - OAK
2 stops27h 06mDelta
Deal found 9/24$503
This Delta deal was found by Cheapflights users on 9/24. 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 12/234:57 pmOAK - PLS
2 stops18h 28mDelta
Wed 1/73:57 pmPLS - OAK
2 stops23h 33mDelta
Deal found 9/24$518
This Southwest deal was found by Cheapflights users on 9/25. 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 9/287:10 amOAK - SJU
2 stops14h 25mSouthwest
Wed 10/17:20 amSJU - OAK
2 stops13h 20mSouthwest
Deal found 9/25$529
This Southwest deal was found by Cheapflights users on 9/23. 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 11/135:40 amOAK - SJU
2 stops12h 40mSouthwest
Mon 11/175:45 amSJU - OAK
2 stops12h 55mSouthwest
Deal found 9/23$537
This Southwest deal was found by Cheapflights users on 9/24. 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 12/166:30 pmOAK - AUA
2 stops16h 30mSouthwest
Fri 12/1912:30 pmAUA - OAK
2 stops15h 50mSouthwest
Deal found 9/24$631
This Southwest deal was found by Cheapflights users on 9/24. 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 11/288:55 pmOAK - SJU
2 stops11h 55mSouthwest
Mon 12/811:20 amSJU - OAK
2 stops12h 30mSouthwest
Deal found 9/24$665
This Delta deal was found by Cheapflights users on 9/24. 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 12/234:57 pmOAK - GCM
2 stops16h 40mDelta
Wed 1/72:00 pmGCM - OAK
2 stops25h 30mDelta
Deal found 9/24$708
This Southwest deal was found by Cheapflights users on 9/24. 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 12/84:30 pmOAK - AUA
2 stops18h 30mSouthwest
Fri 12/124:00 pmAUA - OAK
2 stops20h 05mSouthwest
Deal found 9/24$709
This Delta deal was found by Cheapflights users on 9/24. 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 12/234:57 pmOAK - GCM
2 stops16h 40mDelta
Mon 12/293:42 pmGCM - OAK
2 stops23h 12mDelta
Deal found 9/24$713
This Delta deal was found by Cheapflights users on 9/24. 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 12/234:57 pmOAK - PLS
2 stops18h 28mDelta
Tue 1/63:57 pmPLS - OAK
2 stops23h 33mDelta
Deal found 9/24$718
This Southwest deal was found by Cheapflights users on 9/23. 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 11/227:45 pmOAK - SJU
2 stops11h 15mSouthwest
Mon 11/245:40 amSJU - OAK
2 stops12h 50mSouthwest
Deal found 9/23$742

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Caribbean Islands 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 September 25, 2025.
Use the filters below to find and compare flights from Oakland to Caribbean Islands that are best for you.

Fly from

Oakland

Fly to

Caribbean Islands

Route

Depart

Return

Price

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 11/8

5:00 pm-11:54 am

2 stops15h 54m

Nassau Intl

Tue 11/11

1:19 pm-12:03 am

2 stops13h 44m

$465

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 1/11

7:30 pm-11:20 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Wed 1/14

5:40 am-2:55 pm

2 stops13h 15m

$481

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sat 11/8

5:00 pm-2:11 pm

2 stops18h 11m

Montego Bay Sangster Intl

Sat 11/15

4:05 pm-4:11 pm

2 stops27h 06m

$503

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Mon 1/5

6:55 pm-1:00 pm

2 stops15h 05m

Nassau Intl

Mon 1/12

1:55 pm-9:45 pm

2 stops10h 50m

$564

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Tue 12/16

6:30 pm-3:00 pm

2 stops16h 30m

Oranjestad Reina Beatrix

Fri 12/19

12:30 pm-12:20 am

2 stops15h 50m

$631

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 11/28

8:55 pm-12:50 pm

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Mon 12/8

11:20 am-7:50 pm

2 stops12h 30m

$665

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Sat 3/21

8:10 pm-2:00 pm

2 stops14h 50m

Providenciales

Mon 3/30

2:40 pm-7:20 am

2 stops19h 40m

$706

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Fri 3/20

7:35 pm-11:55 am

2 stops13h 20m

Providenciales

Fri 3/27

2:40 pm-6:50 am

2 stops19h 10m

$706

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Sun 12/28

5:53 am-12:37 pm

2 stops27h 44m

George Town Owen Roberts Intl

Wed 1/7

2:00 pm-12:30 pm

2 stops25h 30m

$708

OaklandGeorge Town

OAK - GCM

OAKGCM

Oakland

Tue 12/23

4:57 pm-12:37 pm

2 stops16h 40m

George Town Owen Roberts Intl

Wed 1/7

2:00 pm-12:30 pm

2 stops25h 30m

$708

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

Showing 1-10 of 54 results
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Best time to book a flight from Oakland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Oakland, California to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $254). Flying from Oakland, California to Caribbean Islands 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 EPX?

Find hourly flight availability from Oakland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 25, 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 Islands as you normally would.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated September 25, 2025.
Get a feel of what it's like to fly with Southwest and Spirit Airlines from Oakland to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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
8,045 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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 Islands. 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 Islands?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Caribbean Islands.

  • How long is the flight from Oakland, California to Caribbean Islands?

    Delta, Southwest, and Alaska Airlines can get you from Oakland, California to Caribbean Islands in just under 11h 50m. Your travel time can differ by up to 25h 26m. The distance from Oakland, California to Caribbean Islands is about 3615 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Oakland, California to Caribbean Islands?

    The most popular route from Oakland, California to Caribbean Islands is Oakland - San Juan Luis Munoz Marin Intl. You may also consider Oakland - Punta Cana or Oakland - Nassau Intl.

  • Can I find deals for flights from Oakland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Oakland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Caribbean Islands.

  • Can I find deals for business class flights from Oakland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Oakland to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $254). Flying from Oakland, California to Caribbean Islands 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.

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Top 2 airlines flying from Oakland to Caribbean Islands

Discover the top 2 airlines that operate flights from Oakland to Caribbean Islands. 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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$278Average$534FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$651FlexibilityNo cancel feeOn-time63%

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