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Oakland

$278+ Cheap flights from Caribbean 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — OAK
mrt. 7 — mrt. 141
za 3/7
za 3/14
1 adult, Economy
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Cheap flight deals from Caribbean to Oakland

Cheapest flights from Caribbean to Oakland
Explore the most affordable flight options available from Caribbean to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on februari 5, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
di 4/286:45 am
SJU
-
OAK
2 stops14h 54m
Alaska Airlines
wo 4/296:46 am
OAK
-
SJU
2 stops13h 16m
Alaska Airlines
Deal found 2/2$674
This Mytrip deal was found by Cheapflights users on 2/4. 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.
do 4/307:39 pm
SDQ
-
OAK
2 stops25h 55m
Multiple Airlines
do 5/78:22 pm
OAK
-
SDQ
3 stops30h 37m
Multiple Airlines
Deal found 2/4$807
This Delta deal was found by Cheapflights users on 2/3. 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.
di 7/286:00 am
SDQ
-
OAK
2 stops20h 49m
Delta
di 8/41:15 pm
OAK
-
SDQ
2 stops21h 11m
Delta
Deal found 2/3$1,118
This Delta deal was found by Cheapflights users on 2/3. 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.
zo 7/267:25 pm
SDQ
-
OAK
2 stops24h 06m
Delta
di 8/41:15 pm
OAK
-
SDQ
2 stops21h 11m
Delta
Deal found 2/3$1,148
This Delta deal was found by Cheapflights users on 2/3. 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.
zo 7/267:25 pm
SDQ
-
OAK
2 stops24h 06m
Delta
do 8/65:55 am
OAK
-
SDQ
2 stops28h 31m
Delta
Deal found 2/3$1,177
This Delta deal was found by Cheapflights users on 2/4. 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.
do 4/307:59 pm
SDQ
-
OAK
2 stops18h 54m
Delta
do 5/712:29 pm
OAK
-
SDQ
2 stops21h 52m
Delta
Deal found 2/4$1,198
This Delta deal was found by Cheapflights users on 2/3. 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.
do 7/307:25 pm
SDQ
-
OAK
2 stops24h 06m
Delta
wo 8/51:15 pm
OAK
-
SDQ
2 stops21h 11m
Delta
Deal found 2/3$1,245
This Delta deal was found by Cheapflights users on 2/3. 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.
zo 7/267:25 pm
SDQ
-
OAK
2 stops24h 06m
Delta
zo 8/25:55 am
OAK
-
SDQ
2 stops28h 31m
Delta
Deal found 2/3$1,272
This Delta deal was found by Cheapflights users on 2/3. 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.
di 7/287:25 pm
SDQ
-
OAK
2 stops24h 06m
Delta
zo 8/25:55 am
OAK
-
SDQ
2 stops28h 31m
Delta
Deal found 2/3$1,286
This Delta deal was found by Cheapflights users on 2/3. 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.
ma 7/276:00 am
SDQ
-
OAK
2 stops20h 49m
Delta
zo 8/25:55 am
OAK
-
SDQ
2 stops28h 31m
Delta
Deal found 2/3$1,316
This American Airlines deal was found by Cheapflights users on 2/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wo 2/45:51 pm
SJU
-
OAK
3 stops26h 32m
Multiple Airlines
wo 2/1110:30 am
OAK
-
SJU
2 stops21h 10m
Multiple Airlines
Deal found 2/4$11,128
This American Airlines deal was found by Cheapflights users on 2/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wo 2/45:51 pm
SJU
-
OAK
3 stops26h 32m
Multiple Airlines
ma 2/98:03 pm
OAK
-
SJU
2 stops21h 36m
Multiple Airlines
Deal found 2/4$11,556

Find flight deals from Caribbean to Oakland

Keep the following information in mind while searching for Caribbean to Oakland flight deals. Data was last updated februari 5, 2026.

Round-trip from

$674
(Alaska Airlines)

One-way from

$278
(Southwest)

Popular in

January

Cheapest in

December

Average price

$437
From Caribbean to Oakland
Search Deals
One-way flight from Caribbean to Oakland
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($89 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 februari 5, 2026.
Use the filters below to find and compare flights from Caribbean to Oakland that are best for you.

Fly from

Caribbean

Fly to

Oakland

Route

Depart

Return

Price

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

di 4/28

6:45 am-6:39 pm

2 stops14h 54m

Oakland

wo 4/29

3:18 pm-4:32 am

2 stops34h 14m

$674

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

do 4/30

7:39 pm-6:34 pm

2 stops25h 55m

Oakland

do 5/7

8:22 pm-5:59 am

3 stops30h 37m

$807

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

wo 7/29

7:25 pm-4:31 pm

2 stops24h 06m

Oakland

wo 8/5

5:55 am-1:26 pm

2 stops28h 31m

$1,118

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

di 7/28

7:25 pm-11:49 pm

2 stops31h 24m

Oakland

wo 8/5

5:55 am-1:26 pm

2 stops28h 31m

$1,118

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

di 7/28

6:00 am-11:49 pm

2 stops20h 49m

Oakland

di 8/4

1:15 pm-1:26 pm

2 stops21h 11m

$1,118

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

zo 7/26

7:25 pm-4:31 pm

2 stops24h 06m

Oakland

wo 8/5

5:55 am-1:26 pm

2 stops28h 31m

$1,148

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

ma 7/27

7:25 pm-11:49 pm

2 stops31h 24m

Oakland

di 8/4

1:15 pm-1:26 pm

2 stops21h 11m

$1,148

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

ma 7/27

6:00 am-11:49 pm

2 stops20h 49m

Oakland

ma 8/3

5:55 am-1:26 pm

2 stops28h 31m

$1,148

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

wo 7/29

7:25 pm-4:31 pm

2 stops24h 06m

Oakland

do 8/6

5:55 am-1:26 pm

2 stops28h 31m

$1,148

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

do 7/30

7:25 pm-4:31 pm

2 stops24h 06m

Oakland

do 8/6

5:55 am-1:26 pm

2 stops28h 31m

$1,148

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 37 results
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Best time to book a flight from Caribbean to Oakland

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

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

Currently, June is the cheapest month in which you can book a flight from Caribbean to Oakland, California (average of $119). Flying from Caribbean to Oakland, California in January is currently the most expensive (average of $325). 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.

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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?

    Most people fly into Oakland (OAK) if they book a flight to Oakland from Caribbean. Oakland is conveniently located just 7.0 mi from Oakland’s city center.

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

    There are many flights that can get you from Caribbean to Oakland, California in 14h 54m. Fly via Alaska Airlines or Delta to get the fastest option. The distance between Caribbean and Oakland, California is about 3615 mi. This flight may include one or multiple stops.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Oakland, Santo Domingo Las Americas - Oakland or Simpson Bay Princess Juliana - Oakland when deciding on the best route from Caribbean to Oakland, California.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Caribbean to Oakland, California (average of $119). Flying from Caribbean to Oakland, California in January is currently the most expensive (average of $325). 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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