What airlines fly to Caribbean Islands?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Caribbean Islands from Oakland, California according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 12 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Oakland to Caribbean Islands?

Southwest, Delta, and Alaska Airlines are the most popular carriers operating from Oakland to Caribbean Islands

When did momondo last update prices for flights from Oakland Airport to Caribbean Islands?

Prices for flights from Oakland Airport to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Oakland Airport to Caribbean Islands?

There is 1 operator available for flights from Oakland Airport to Caribbean Islands as of December 2025.

How old do you have to be to fly from Oakland Airport to Caribbean Islands?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oakland Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$203 Cheap Flights from Oakland to Caribbean Islands in 2025/26

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Find the cheapest flights from Oakland, California to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:25 pm - 11:20 am

OAK

SJU

11h 55m2 stops

10:20 am - 7:50 pm

SJU

OAK

13h 30m2 stops

$317Southwest

Mon, Feb 2 - Tue, Feb 10

9:10 am - 12:40 am

OAK

SJU

11h 30m2 stops

10:20 am - 7:50 pm

SJU

OAK

13h 30m2 stops

$408Southwest

Sun, Feb 1 - Tue, Feb 10

9:40 am - 12:35 am

OAK

SJU

10h 55m2 stops

5:35 am - 3:25 pm

SJU

OAK

13h 50m2 stops

$420Southwest

Tue, Feb 3 - Tue, Feb 17

9:40 am - 12:35 am

OAK

SJU

10h 55m2 stops

5:40 am - 2:55 pm

SJU

OAK

13h 15m2 stops

$491Southwest

Wed, Jan 7 - Tue, Jan 13

7:50 am - 12:25 am

OAK

SJU

13h 35m2 stops

8:35 pm - 10:25 am

SJU

OAK

16h 50m2 stops

$499Southwest

Thu, Jun 11 - Tue, Jun 30

7:25 am - 12:35 am

OAK

SJU

13h 10m2 stops

12:10 pm - 9:45 pm

SJU

OAK

13h 35m2 stops

$547Southwest

Tue, Jan 13 - Mon, Jan 26

5:00 pm - 2:20 pm

OAK

PUJ

17h 20m2 stops

2:55 pm - 4:14 pm

PUJ

OAK

29h 19m2 stops

$563Delta

Mon, Feb 2 - Mon, Feb 9

12:34 pm - 11:08 am

OAK

NAS

19h 34m2 stops

1:41 pm - 10:53 pm

NAS

OAK

12h 12m2 stops

$623Delta

Sat, Jan 3 - Wed, Jan 7

11:07 pm - 12:54 am

OAK

PUJ

22h 47m2 stops

6:15 am - 7:57 pm

PUJ

OAK

16h 42m2 stops

$625Multiple Airlines

Tue, Mar 17 - Sun, Mar 22

5:55 am - 8:05 pm

OAK

KIN

12h 10m2 stops

9:00 am - 9:41 pm

KIN

OAK

14h 41m2 stops

$953Delta

Tue, Apr 14 - Sat, Apr 18

Southwest flights from Oakland, California to Caribbean Islands

Our best Southwest deals on Oakland, California to Caribbean Islands flight tickets

Southwest

Feb 2

OAK7:25 pmOakland

11h 55m

2 stops

SJU11:20 amSan Juan Luis Munoz Marin Intl

Feb 10

SJU10:20 amSan Juan Luis Munoz Marin Intl

13h 30m

2 stops

OAK7:50 pmOakland

$317

Find similar

Southwest

Feb 1

OAK9:10 amOakland

11h 30m

2 stops

SJU12:40 amSan Juan Luis Munoz Marin Intl

Feb 10

SJU10:20 amSan Juan Luis Munoz Marin Intl

13h 30m

2 stops

OAK7:50 pmOakland

$408

Find similar

Southwest

Feb 3

OAK9:40 amOakland

10h 55m

2 stops

SJU12:35 amSan Juan Luis Munoz Marin Intl

Feb 17

SJU5:35 amSan Juan Luis Munoz Marin Intl

13h 50m

2 stops

OAK3:25 pmOakland

$420

Find similar

Alaska Airlines flights from Oakland, California to Caribbean Islands

Our best Alaska Airlines deals on Oakland, California to Caribbean Islands flight tickets

Alaska Airlines

Jan 23

OAK8:10 amOakland

26h 38m

2 stops

SJU2:48 pmSan Juan Luis Munoz Marin Intl

Jan 27

SJU6:00 amSan Juan Luis Munoz Marin Intl

32h 28m

2 stops

OAK10:28 amOakland

$776

Find similar

Alaska Airlines

Jan 23

OAK8:10 amOakland

26h 38m

2 stops

SJU2:48 pmSan Juan Luis Munoz Marin Intl

Jan 28

SJU6:00 amSan Juan Luis Munoz Marin Intl

33h 03m

2 stops

OAK11:03 amOakland

$781

Find similar

Alaska Airlines

Jan 23

OAK8:10 amOakland

26h 38m

2 stops

SJU2:48 pmSan Juan Luis Munoz Marin Intl

Jan 29

SJU6:00 amSan Juan Luis Munoz Marin Intl

42h 40m

2 stops

OAK8:40 pmOakland

$782

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Oakland, California to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 2/2

7:25 pm-11:20 am

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Tue 2/10

10:20 am-7:50 pm

2 stops13h 30m

$317

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 2/1

9:10 am-12:40 am

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Tue 2/10

10:20 am-7:50 pm

2 stops13h 30m

$408

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 2/3

9:40 am-12:35 am

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Tue 2/17

5:35 am-3:25 pm

2 stops13h 50m

$420

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 1/7

9:40 am-12:35 am

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Tue 1/13

5:40 am-2:55 pm

2 stops13h 15m

$491

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 6/11

7:50 am-12:25 am

2 stops13h 35m

San Juan Luis Munoz Marin Intl

Tue 6/30

8:35 pm-10:25 am

2 stops16h 50m

$499

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 1/13

7:25 am-12:35 am

2 stops13h 10m

San Juan Luis Munoz Marin Intl

Mon 1/26

12:10 pm-9:45 pm

2 stops13h 35m

$547

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Mon 2/2

5:00 pm-2:20 pm

2 stops17h 20m

Punta Cana

Mon 2/9

2:55 pm-4:14 pm

2 stops29h 19m

$563

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 1/3

12:34 pm-11:08 am

2 stops19h 34m

Nassau Intl

Wed 1/7

1:41 pm-10:53 pm

2 stops12h 12m

$623

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Tue 3/17

11:07 pm-12:54 am

2 stops22h 47m

Punta Cana

Sun 3/22

6:15 am-7:57 pm

2 stops16h 42m

$625

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Tue 4/14

5:55 am-8:05 pm

2 stops12h 10m

Kingston Norman Manley

Sat 4/18

9:00 am-9:41 pm

2 stops14h 41m

$953

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Oakland, California to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Oakland, California, with most prices found around $382. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $412.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Oakland, California to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $387. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $825. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Oakland, California to Caribbean Islands in the afternoon for as low as $410. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the evening because they tend to be around $535. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Oakland, California to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Oakland, California to Caribbean Islands.

Cheap Oakland, California to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Caribbean Islands

Fastest flight time	10h 50m
Direct flights	None

The fastest flight from Oakland, California to Caribbean Islands takes 10h 50m

There are no direct flights from Oakland, California to Caribbean Islands. There are no popular flight routes from Oakland, California to Caribbean Islands.

Search flight deals

When did momondo last update prices for flights from Oakland Airport to Caribbean Islands?
Prices for flights from Oakland Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Oakland Airport to Caribbean Islands?
There is 1 operator available for flights from Oakland Airport to Caribbean Islands as of December 2025.
How old do you have to be to fly from Oakland Airport to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oakland Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Oakland, California to Caribbean Islands?
Based on momondo bookings for flights between Oakland, California and Caribbean Islands, the leading plane model is Boeing 737 MAX 8, making up 22.66% of the total bookings. Other popular models include Airbus A320-100/200 with 13.21%, Airbus A320neo with 11.83%, and Boeing 737-700 Passenger/BBJ1 (winglets) with 10.85%.

Best airlines flying from Oakland, California to Caribbean Islands

Compare and see reviews for airlines that fly from Oakland, California to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $385	Free Cancellation	Rating 8.0 4,254 reviews		Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Oakland to Caribbean Islands?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean Islands from Oakland.

Can I find flights from Oakland to Caribbean Islands with flexible booking policies on momondo?

Flights from Oakland to Caribbean Islands with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Oakland to Caribbean Islands?

momondo helps you find the best flight between Oakland and Caribbean Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Oakland to Caribbean Islands right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Oakland and alert you when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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Cheap flights from Oakland, California to Caribbean Islands from $203

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Oakland, California to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Southwest flights from Oakland, California to Caribbean Islands

Our best Southwest deals on Oakland, California to Caribbean Islands flight tickets

Alaska Airlines flights from Oakland, California to Caribbean Islands

Our best Alaska Airlines deals on Oakland, California to Caribbean Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Oakland, California to Caribbean Islands that are best for you.

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Oakland, California to Caribbean Islands

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Oakland, California, with most prices found around $382. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $412.

What is the cheapest day to depart on your flight to Caribbean Islands?

What is the cheapest time of day to depart on your flight to Caribbean Islands?

Can stopping save me money on Oakland, California to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Oakland, California to Caribbean Islands.

What is the cheapest airline that flies from Oakland to Caribbean Islands?

Southwest, Delta, and Alaska Airlines are the most popular carriers operating from Oakland to Caribbean Islands

What airlines fly to Caribbean Islands?

Cheap Oakland, California to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Caribbean Islands

Fastest flight time

Direct flights

When did momondo last update prices for flights from Oakland Airport to Caribbean Islands?

How many operators does momondo search for flights from Oakland Airport to Caribbean Islands?

How old do you have to be to fly from Oakland Airport to Caribbean Islands?

What documentation or ID do you need to fly to Caribbean Islands?

What is the most popular plane model from Oakland, California to Caribbean Islands?

Best airlines flying from Oakland, California to Caribbean Islands

Compare and see reviews for airlines that fly from Oakland, California to Caribbean Islands with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Oakland to Caribbean Islands?

Can I find flights from Oakland to Caribbean Islands with flexible booking policies on momondo?

How can momondo help me find flights from Oakland to Caribbean Islands?

I’m not ready to book a flight from Oakland to Caribbean Islands right now. Can momondo alert me if prices change?

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo