HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oakland

$196+ 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — OAK
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean to Oakland with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean to Oakland

Keep the following information in mind while searching for Caribbean to Oakland flight deals. Data was last updated March 28, 2025.

Round-trip from

$752
(Mytrip)

One-way from

$196
(Mytrip)

Popular in

June

Cheapest in

October

Average price

$489
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 ($94 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

Find 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 March 28, 2025.

This Mytrip deal was found by Cheapflights users on 3/26. 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.
Tue 5/273:35 pmSDQ - OAK
2 stops33h 50mMultiple Airlines
Wed 6/47:19 pmOAK - SDQ
2 stops30h 11mMultiple Airlines
Deal found 3/26$752
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 4/152:43 pmSDQ - OAK
2 stops12h 00mDelta
Mon 4/215:10 pmOAK - SDQ
2 stops17h 05mDelta
Deal found 3/25$917
This Delta deal was found by Cheapflights users on 3/27. 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 7/82:28 pmSJU - OAK
2 stops12h 15mDelta
Sun 7/135:15 pmOAK - SJU
2 stops16h 55mDelta
Deal found 3/27$1,011
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2612:34 pmSJU - OAK
2 stops13h 52mSpirit Airlines
Thu 7/249:09 pmOAK - SJU
2 stops12h 38mSpirit Airlines
Deal found 3/27$1,172
This Alaska Airlines deal was found by Cheapflights users on 3/27. 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.
Wed 6/2512:59 amSJU - OAK
2 stops26h 00mAlaska Airlines
Tue 7/228:00 amOAK - SJU
2 stops27h 18mAlaska Airlines
Deal found 3/27$1,310
This Delta deal was found by Cheapflights users on 3/27. 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.
Thu 7/101:10 pmPUJ - OAK
2 stops13h 33mDelta
Sun 7/135:15 pmOAK - PUJ
2 stops15h 30mDelta
Deal found 3/27$3,789

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 March 28, 2025.
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

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

Tue 5/27

3:35 pm-10:25 pm

2 stops33h 50m

Oakland

Wed 6/4

7:19 pm-4:30 am

2 stops30h 11m

$752

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

Tue 4/15

2:43 pm-11:43 pm

2 stops12h 00m

Oakland

Mon 4/21

5:10 pm-1:15 pm

2 stops17h 05m

$917

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Tue 7/8

2:28 pm-11:43 pm

2 stops12h 15m

Oakland

Sun 7/13

5:15 pm-1:10 pm

2 stops16h 55m

$1,011

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Thu 6/26

12:34 pm-11:26 pm

2 stops13h 52m

Oakland

Thu 7/24

9:09 pm-12:47 pm

2 stops12h 38m

$1,172

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Wed 6/25

12:59 am-11:59 pm

2 stops26h 00m

Oakland

Tue 7/22

8:00 am-2:18 pm

2 stops27h 18m

$1,310

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

Thu 7/10

1:10 pm-11:43 pm

2 stops13h 33m

Oakland

Sun 7/13

5:15 pm-11:45 am

2 stops15h 30m

$3,789

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Thu 4/10

12:54 am-6:49 am

2 stops32h 55m

$196

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Wed 4/9

2:13 pm-11:46 pm

2 stops12h 33m

$268

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Sat 6/21

4:20 pm-4:21 pm

1 stop27h 01m

$313

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

Tue 4/15

6:10 pm-12:20 pm

3 stops21h 10m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 14 results
1
2

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, April is the cheapest month in which you can book a flight from Caribbean to Oakland, California (average of $183). Flying from Caribbean 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 CB to OAK?

Find hourly flight availability from Caribbean 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 March 28, 2025.

When flying from Caribbean to Oakland, California, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Oakland by month

Plan your trip to Oakland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Oakland, California ranges from 0.0 - 4.8 inches per month. January is typically the wettest month, when rainfall can reach 4.8 in. July is typically the driest time to visit Oakland, California when rainfall is around 0.0 in.

Temperature in Oakland by month

Plan your trip to Oakland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Oakland, California, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 66.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. 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 Oakland. Reviews last updated March 28, 2025.
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot
Alaska Airlines
8.0
Very good
9,798 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot
Delta
8.0
Very good
7,896 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot
Sun Country Air
6.9
Okay
348 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot
Spirit Airlines
6.3
Okay
7,881 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Seleste,Dec 2024

FAT - SAN

The attention and efficiency of the staff and the good handling of the pilot

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.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $196. Delta flights start at $268 while deals on Sun Country Air start at $313 one-way.

  • 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 Oranjestad Reina Beatrix - 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, April is the cheapest month in which you can book a flight from Caribbean to Oakland, California (average of $183). Flying from Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Las Vegas flights
Newark to Las Vegas flights
John F Kennedy Intl to Los Angeles flights
Newark to Los Angeles flights
LaGuardia to Las Vegas flights
O'Hare Intl to Las Vegas flights
LaGuardia to Los Angeles flights
Dallas/Fort Worth to Las Vegas flights
Seattle to Las Vegas flights
Newark to San Francisco flights
Denver to Las Vegas flights
Los Angeles to Las Vegas flights
Seattle to Los Angeles flights
Burbank to Las Vegas flights
Boston to Las Vegas flights
Dulles Intl to Las Vegas flights
San Francisco to Los Angeles flights
Boston to Los Angeles flights
Atlanta to Las Vegas flights
San Francisco to Las Vegas flights
John F Kennedy Intl to San Francisco flights
Hobby to Las Vegas flights
O'Hare Intl to Los Angeles flights
Dallas/Fort Worth to Los Angeles flights
San Jose to Los Angeles flights
Minneapolis to Las Vegas flights
John F Kennedy Intl to San Diego flights
Los Angeles to San Francisco flights
Reagan-National to Las Vegas flights
Seattle to San Diego flights
Reagan-National to Los Angeles flights
Los Angeles to San Jose flights
Newark to Burbank flights
Santa Ana to Las Vegas flights
Dulles Intl to Los Angeles flights
Newark to San Diego flights
Hobby to Los Angeles flights
George Bush Intcntl to Las Vegas flights
Los Angeles to Oakland flights
San Francisco to Ontario flights
LaGuardia to San Francisco flights
Dulles Intl to San Francisco flights
Baltimore to Las Vegas flights
Seattle to Santa Ana flights
Oakland to Las Vegas flights
Detroit to Las Vegas flights
Portland to Los Angeles flights
Seattle to Burbank flights
Oakland to Los Angeles flights
Baltimore to Los Angeles flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.