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 41% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 11 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 and Delta 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 June 2026.

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.

$233 Cheap Flights from Oakland, California to Caribbean Islands in 2026

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.

7:40 pm - 11:00 am

OAK

SJU

12h 20m

2 stops

1:45 pm - 10:30 pm

SJU

OAK

11h 45m

2 stops

$436Southwest

Mon, Sep 14 - Wed, Sep 23

7:40 pm - 11:00 am

OAK

SJU

12h 20m

2 stops

5:05 am - 1:40 pm

SJU

OAK

11h 35m

2 stops

$451Southwest

Mon, Sep 14 - Sat, Sep 19

6:25 am - 9:55 pm

OAK

SJU

11h 30m

2 stops

6:15 am - 2:20 pm

SJU

OAK

12h 05m

2 stops

$466Southwest

Tue, Nov 10 - Mon, Nov 16

6:00 am - 11:51 am

OAK

NAS

26h 51m

2 stops

1:16 pm - 11:51 am

NAS

OAK

25h 35m

2 stops

$562Delta

Wed, Sep 30 - Tue, Oct 6

6:05 pm - 12:25 pm

OAK

PUJ

15h 20m

2 stops

2:45 pm - 7:40 am

PUJ

OAK

19h 55m

2 stops

$565Southwest

Tue, Oct 27 - Wed, Oct 28

6:30 pm - 12:50 pm

OAK

MBJ

15h 20m

2 stops

1:50 pm - 7:50 am

MBJ

OAK

21h 00m

2 stops

$567Southwest

Mon, Nov 30 - Tue, Dec 8

7:50 pm - 10:45 am

OAK

SJU

11h 55m

2 stops

9:05 pm - 11:35 am

SJU

OAK

17h 30m

2 stops

$591Southwest

Sat, Jul 25 - Sun, Aug 2

5:05 pm - 12:45 pm

OAK

SJU

15h 40m

2 stops

1:55 pm - 11:56 pm

SJU

OAK

14h 01m

2 stops

$593Delta

Sat, Dec 5 - Sat, Dec 12

6:00 am - 11:52 am

OAK

NAS

26h 52m

2 stops

1:16 pm - 11:51 am

NAS

OAK

25h 35m

2 stops

$626Delta

Fri, Oct 2 - Tue, Oct 6

11:15 pm - 11:30 pm

OAK

PUJ

21h 15m

2 stops

8:02 pm - 6:34 pm

PUJ

OAK

25h 32m

2 stops

$743Multiple Airlines

Tue, Aug 11 - Tue, Aug 18

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Alaska Airlines flights from Oakland, California to Caribbean Islands

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

Alaska Airlines

Nov 18

OAK6:20 amOakland

19h 10m

2 stops

SJU5:30 amSan Juan Luis Munoz Marin Intl

Dec 2

SJU7:00 amSan Juan Luis Munoz Marin Intl

31h 05m

2 stops

OAK10:05 amOakland

$803

Alaska Airlines

Dec 6

OAK6:30 amOakland

28h 27m

2 stops

SJU2:57 pmSan Juan Luis Munoz Marin Intl

Dec 12

SJU7:00 amSan Juan Luis Munoz Marin Intl

31h 05m

2 stops

OAK10:05 amOakland

$891

Alaska Airlines

Oct 1

OAK7:51 pmOakland

15h 54m

2 stops

SJU2:45 pmSan Juan Luis Munoz Marin Intl

Oct 5

SJU6:00 amSan Juan Luis Munoz Marin Intl

20h 08m

2 stops

OAK11:08 pmOakland

$939

Southwest flights from Oakland, California to Caribbean Islands

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

Southwest

Sep 14

OAK7:40 pmOakland

12h 20m

2 stops

SJU11:00 amSan Juan Luis Munoz Marin Intl

Sep 23

SJU1:45 pmSan Juan Luis Munoz Marin Intl

11h 45m

2 stops

OAK10:30 pmOakland

$436

Southwest

Sep 14

OAK7:40 pmOakland

12h 20m

2 stops

SJU11:00 amSan Juan Luis Munoz Marin Intl

Sep 19

SJU5:05 amSan Juan Luis Munoz Marin Intl

11h 35m

2 stops

OAK1:40 pmOakland

$451

Southwest

Nov 10

OAK6:25 amOakland

11h 30m

2 stops

SJU9:55 pmSan Juan Luis Munoz Marin Intl

Nov 16

SJU6:15 amSan Juan Luis Munoz Marin Intl

12h 05m

2 stops

OAK2:20 pmOakland

$466

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

Cheapest round-trip

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 9/14

7:40 pm-11:00 am

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Wed 9/23

1:45 pm-10:30 pm

2 stops11h 45m

$436

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 9/14

7:40 pm-11:00 am

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Sat 9/19

5:05 am-1:40 pm

2 stops11h 35m

$451

Quickest round-trip

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 11/10

6:25 am-9:55 pm

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Mon 11/16

6:15 am-2:20 pm

2 stops12h 05m

$466

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Wed 9/30

6:00 am-11:51 am

2 stops26h 51m

Nassau Intl

Tue 10/6

1:16 pm-11:51 am

2 stops25h 35m

$562

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Tue 10/27

6:05 pm-12:25 pm

2 stops15h 20m

Punta Cana

Wed 10/28

2:45 pm-7:40 am

2 stops19h 55m

$565

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Mon 11/30

6:30 pm-12:50 pm

2 stops15h 20m

Montego Bay Sangster Intl

Tue 12/8

1:50 pm-7:50 am

2 stops21h 00m

$567

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 7/25

7:50 pm-10:45 am

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Sun 8/2

9:05 pm-11:35 am

2 stops17h 30m

$591

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 12/5

5:05 pm-12:45 pm

2 stops15h 40m

San Juan Luis Munoz Marin Intl

Sat 12/12

1:55 pm-11:56 pm

2 stops14h 01m

$593

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Fri 10/2

6:00 am-11:52 am

2 stops26h 52m

Nassau Intl

Tue 10/6

1:16 pm-11:51 am

2 stops25h 35m

$626

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Tue 8/11

11:15 pm-11:30 pm

2 stops21h 15m

Punta Cana

Tue 8/18

8:02 pm-6:34 pm

2 stops25h 32m

$743

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

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 25m
Direct flights	None

The fastest flight from Oakland, California to Caribbean Islands takes 10h 25m

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

Frequently asked questions about flying from Oakland, California 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 June 2026.
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 23.05% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 22.14%, Airbus A320neo with 11.84%, and Airbus A321neo with 7.68%.

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 $410	Free Cancellation	Rating 7.9 4,246 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.