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$280+ Cheap flights from Caribbean Islands to Oakland, CA (OAK)

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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — OAK
oct. 25 — nov. 11
sáb. 10/25
sáb. 11/1
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Oakland

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

Round-trip from

$591
(Southwest)

One-way from

$280
(Delta)
From Caribbean Islands to Oakland
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One-way flight from Caribbean Islands to Oakland
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Find flight deals from Caribbean Islands to Oakland

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

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.
jue. 11/205:45 amSJU - OAK
2 stops12h 20mSouthwest
vie. 11/286:05 pmOAK - SJU
2 stops12h 20mSouthwest
Deal found 9/24$591
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.
mié. 11/195:45 amSJU - OAK
2 stops12h 20mSouthwest
sáb. 11/298:55 pmOAK - SJU
2 stops11h 20mSouthwest
Deal found 9/24$592
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.
jue. 11/205:45 amSJU - OAK
2 stops12h 20mSouthwest
sáb. 11/297:45 pmOAK - SJU
2 stops10h 45mSouthwest
Deal found 9/24$615
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.
sáb. 11/223:50 pmSJU - OAK
1 stop13h 40mSouthwest
sáb. 11/297:45 pmOAK - SJU
2 stops10h 45mSouthwest
Deal found 9/24$684
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.
jue. 11/205:45 amSJU - OAK
2 stops12h 20mSouthwest
dom. 11/305:00 amOAK - SJU
2 stops11h 40mSouthwest
Deal found 9/24$725
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.
sáb. 11/226:35 amSJU - OAK
2 stops18h 10mSouthwest
dom. 11/305:00 amOAK - SJU
2 stops11h 40mSouthwest
Deal found 9/24$794
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/93:00 pmSJU - OAK
2 stops36h 03mAlaska Airlines
lun. 10/136:40 amOAK - SJU
2 stops28h 45mAlaska Airlines
Deal found 9/23$1,565

Cheapflights Fare Finder

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

Fly from

Caribbean Islands

Fly to

Oakland

Route

Depart

Return

Price

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

jue. 11/20

5:45 am-2:05 pm

2 stops12h 20m

Oakland

vie. 11/28

6:05 pm-10:25 am

2 stops12h 20m

$591

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

mié. 11/19

5:45 am-2:05 pm

2 stops12h 20m

Oakland

sáb. 11/29

8:55 pm-12:15 pm

2 stops11h 20m

$592

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

vie. 11/21

5:35 am-2:35 pm

2 stops13h 00m

Oakland

sáb. 11/29

7:45 pm-10:30 am

2 stops10h 45m

$592

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

jue. 11/20

5:45 am-2:05 pm

2 stops12h 20m

Oakland

sáb. 11/29

7:45 pm-10:30 am

2 stops10h 45m

$615

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

sáb. 11/22

3:50 pm-1:30 am

1 stop13h 40m

Oakland

sáb. 11/29

7:45 pm-10:30 am

2 stops10h 45m

$684

OranjestadOakland

AUA - OAK

AUAOAK

Oranjestad Reina Beatrix

mar. 3/10

1:10 pm-11:53 pm

2 stops13h 43m

Oakland

jue. 3/12

5:55 am-11:55 am

2 stops27h 00m

$699

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

jue. 11/20

5:45 am-2:05 pm

2 stops12h 20m

Oakland

dom. 11/30

5:00 am-8:40 pm

2 stops11h 40m

$725

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

vie. 2/27

7:20 am-9:08 am

2 stops29h 48m

Oakland

lun. 3/2

6:30 am-9:55 pm

2 stops35h 25m

$993

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

vie. 2/13

3:40 pm-12:30 pm

2 stops24h 50m

Oakland

mar. 2/17

5:05 pm-11:59 pm

2 stops26h 54m

$1,175

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

jue. 10/9

3:00 pm-12:03 am

2 stops36h 03m

Oakland

lun. 10/13

6:40 am-2:25 pm

2 stops28h 45m

$1,565

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

Showing 1-10 of 27 results
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Best time to book a flight from Caribbean Islands to Oakland

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

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

Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Oakland, California (average of $183). Flying from Caribbean Islands to Oakland, California in November is currently the most expensive (average of $259). 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 EPX to OAK?

Find hourly flight availability from Caribbean Islands to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 25, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Oakland, California as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Oakland. 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 into for flights to Oakland from Caribbean Islands?

    For a flight from Caribbean Islands to Oakland, you will be flying into Oakland. Oakland (OAK) is just 7.0 mi from the center of the city.

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

    For as low as $591, Southwest can have you in Oakland, California from Caribbean Islands in 12h 20m. Airlines will cover a distance of 3615 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Caribbean Islands to Oakland, California one-way?

    $280 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and Alaska Airlines, with prices starting from $289 and $428, respectively.

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

    The most popular route from Caribbean Islands to Oakland, California is San Juan Luis Munoz Marin Intl - Oakland. You may also consider Santo Domingo Las Americas - Oakland or Santiago de los Caballeros - Oakland.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Oakland, California (average of $183). Flying from Caribbean Islands to Oakland, California in November is currently the most expensive (average of $259). 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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