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Caribbean Islands

$139+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
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 August 11, 2025.

Round-trip from

$322
(CheapOair)

One-way from

$139
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$524
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. 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 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 August 11, 2025.

This CheapOair deal was found by Cheapflights users on 8/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/12:39 pmOAK - SJU
2 stops20h 04mSpirit Airlines
Mon 10/610:42 amSJU - OAK
2 stops15h 50mSpirit Airlines
Deal found 8/10$322
This FlightHub deal was found by Cheapflights users on 8/9. 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.
Sat 10/186:00 amOAK - SJU
2 stops28h 53mSpirit Airlines
Sat 10/255:18 pmSJU - OAK
2 stops41h 20mSpirit Airlines
Deal found 8/9$347
This CheapOair deal was found by Cheapflights users on 8/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/172:39 pmOAK - SJU
2 stops20h 04mSpirit Airlines
Mon 9/2210:42 amSJU - OAK
2 stops15h 50mSpirit Airlines
Deal found 8/9$362
This CheapOair deal was found by Cheapflights users on 8/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:30 amOAK - SJU
2 stops15h 24mSpirit Airlines
Mon 9/2910:42 amSJU - OAK
2 stops15h 50mSpirit Airlines
Deal found 8/9$363
This Delta deal was found by Cheapflights users on 8/8. 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 10/255:59 pmOAK - SJU
2 stops14h 42mDelta
Sat 11/17:15 amSJU - OAK
2 stops17h 17mDelta
Deal found 8/8$369
This Mytrip deal was found by Cheapflights users on 8/9. 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.
Fri 9/266:30 amOAK - SJU
3 stops28h 41mSpirit Airlines
Mon 9/2910:42 amSJU - OAK
2 stops15h 50mSpirit Airlines
Deal found 8/9$387
This CheapOair deal was found by Cheapflights users on 8/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/132:39 pmOAK - MBJ
2 stops18h 26mSpirit Airlines
Fri 9/1910:52 amMBJ - OAK
2 stops14h 40mSpirit Airlines
Deal found 8/11$403
This Mytrip deal was found by Cheapflights users on 8/9. 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.
Sat 8/238:13 amOAK - SJU
2 stops31h 38mSpirit Airlines
Sat 8/3010:10 amSJU - OAK
3 stops24h 08mSpirit Airlines
Deal found 8/9$404
This Southwest deal was found by Cheapflights users on 8/11. 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 11/137:45 pmOAK - SJU
2 stops11h 15mSouthwest
Sat 11/226:35 amSJU - OAK
2 stops18h 10mSouthwest
Deal found 8/11$415
This CheapOair deal was found by Cheapflights users on 8/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/272:39 pmOAK - PUJ
2 stops20h 35mSpirit Airlines
Sat 10/412:36 pmPUJ - OAK
2 stops13h 56mSpirit Airlines
Deal found 8/9$437
This FlightHub deal was found by Cheapflights users on 8/10. 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.
Tue 9/302:39 pmOAK - PUJ
2 stops20h 35mSpirit Airlines
Tue 10/712:40 pmPUJ - OAK
2 stops21h 58mSpirit Airlines
Deal found 8/10$448
This CheapOair deal was found by Cheapflights users on 8/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/272:39 pmOAK - MBJ
2 stops18h 26mSpirit Airlines
Sat 10/412:10 pmMBJ - OAK
2 stops13h 22mSpirit Airlines
Deal found 8/9$454

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 August 11, 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

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 10/1

2:39 pm-1:43 pm

2 stops20h 04m

San Juan Luis Munoz Marin Intl

Mon 10/6

10:42 am-11:32 pm

2 stops15h 50m

$322

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 10/18

6:00 am-1:53 pm

2 stops28h 53m

San Juan Luis Munoz Marin Intl

Sat 10/25

5:18 pm-7:38 am

2 stops41h 20m

$347

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 9/17

2:39 pm-1:43 pm

2 stops20h 04m

San Juan Luis Munoz Marin Intl

Mon 9/22

10:42 am-11:32 pm

2 stops15h 50m

$362

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 9/25

6:30 am-12:54 am

2 stops15h 24m

San Juan Luis Munoz Marin Intl

Mon 9/29

10:42 am-11:32 pm

2 stops15h 50m

$363

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 10/25

5:59 pm-11:41 am

2 stops14h 42m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:15 am-9:32 pm

2 stops17h 17m

$369

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 9/26

6:30 am-2:11 pm

3 stops28h 41m

San Juan Luis Munoz Marin Intl

Mon 9/29

10:42 am-11:32 pm

2 stops15h 50m

$387

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sat 9/13

2:39 pm-11:05 am

2 stops18h 26m

Montego Bay Sangster Intl

Fri 9/19

10:52 am-11:32 pm

2 stops14h 40m

$403

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 8/23

8:13 am-6:51 pm

2 stops31h 38m

San Juan Luis Munoz Marin Intl

Sat 8/30

10:10 am-7:18 am

3 stops24h 08m

$404

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 11/13

7:45 pm-11:00 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Sat 11/22

3:50 pm-1:30 am

1 stop13h 40m

$415

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sat 9/27

2:39 pm-2:14 pm

2 stops20h 35m

Punta Cana

Sat 10/4

12:36 pm-11:32 pm

2 stops13h 56m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 47 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 August 11, 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 August 11, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,978 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
8,043 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Boarding

8.1

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 - Montego Bay Sangster Intl or Oakland - Punta Cana.

  • 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.

See more FAQs

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Alternative routes for Oakland to Caribbean Islands

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 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$260Average$419FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$683FlexibilityNo cancel feeOn-time63%

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