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$204+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — OAK
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
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 August 13, 2025.

Round-trip from

$451
(Priceline)

One-way from

$204
(FlightHub)
From Caribbean Islands to Oakland
Search Deals
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 August 13, 2025.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:40 pmPUJ - OAK
2 stops13h 52mSpirit Airlines
Thu 10/22:39 pmOAK - PUJ
2 stops20h 35mSpirit Airlines
Deal found 8/11$451
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/291:52 pmSJU - OAK
2 stops20h 26mSpirit Airlines
Sat 9/66:30 amOAK - SJU
2 stops30h 48mSpirit Airlines
Deal found 8/11$485
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/214:12 pmSJU - OAK
3 stops34h 15mSpirit Airlines
Thu 9/42:39 pmOAK - SJU
3 stops31h 15mSpirit Airlines
Deal found 8/11$521
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:42 pmSJU - OAK
2 stops32h 45mSpirit Airlines
Fri 8/296:00 amOAK - SJU
2 stops24h 05mSpirit Airlines
Deal found 8/11$574
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:42 pmSJU - OAK
2 stops32h 45mSpirit Airlines
Sun 8/318:13 amOAK - SJU
2 stops21h 52mSpirit Airlines
Deal found 8/11$595
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/144:12 pmSJU - OAK
2 stops18h 06mSpirit Airlines
Fri 8/226:00 amOAK - SJU
2 stops24h 05mSpirit Airlines
Deal found 8/11$731
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/259:38 amPUJ - OAK
2 stops30h 56mMultiple Airlines
Thu 10/210:00 pmOAK - PUJ
1 stop14h 45mMultiple Airlines
Deal found 8/11$835
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/167:30 amSJU - OAK
2 stops18h 16mDelta
Sat 8/234:58 pmOAK - SJU
2 stops15h 42mDelta
Deal found 8/11$995
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/303:30 pmSJU - OAK
2 stops35h 29mAlaska Airlines
Sun 9/78:00 amOAK - SJU
2 stops27h 15mAlaska Airlines
Deal found 8/11$1,017
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/277:30 amSJU - OAK
2 stops11h 46mDelta
Sat 9/64:58 pmOAK - SJU
2 stops15h 42mDelta
Deal found 8/11$1,022

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 August 13, 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

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

Thu 9/25

12:40 pm-11:32 pm

2 stops13h 52m

Oakland

Thu 10/2

2:39 pm-2:14 pm

2 stops20h 35m

$451

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Fri 8/29

1:52 pm-7:18 am

2 stops20h 26m

Oakland

Sat 9/6

6:30 am-4:18 pm

2 stops30h 48m

$485

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Fri 8/22

5:42 pm-11:27 pm

2 stops32h 45m

Oakland

Fri 8/29

6:00 am-9:05 am

2 stops24h 05m

$574

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

Thu 9/25

9:38 am-1:34 pm

2 stops30h 56m

Oakland

Thu 10/2

10:00 pm-3:45 pm

1 stop14h 45m

$835

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Fri 8/22

2:40 pm-11:50 pm

2 stops12h 10m

Oakland

Sat 8/30

4:58 pm-11:40 am

2 stops15h 42m

$995

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Fri 8/22

2:40 pm-11:50 pm

2 stops12h 10m

Oakland

Sun 8/31

6:00 am-10:07 pm

2 stops13h 07m

$995

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Sat 8/30

3:30 pm-11:59 pm

2 stops35h 29m

Oakland

Sun 9/7

8:00 am-2:15 pm

2 stops27h 15m

$1,017

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Wed 8/27

7:30 am-10:46 pm

2 stops18h 16m

Oakland

Wed 9/3

4:58 pm-1:30 pm

2 stops17h 32m

$1,022

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Fri 8/29

7:30 am-10:46 pm

2 stops18h 16m

Oakland

Wed 9/3

4:58 pm-1:30 pm

2 stops17h 32m

$1,022

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Sat 8/30

7:30 am-4:16 pm

2 stops11h 46m

Oakland

Wed 9/3

4:58 pm-1:30 pm

2 stops17h 32m

$1,022

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 37 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 August 13, 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.

  • 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 Oranjestad Reina Beatrix - 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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