What airlines fly to Caribbean?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Caribbean 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. Keep in mind that there are 10 different airlines that fly to Caribbean 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?

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

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

Prices for flights from Oakland Airport to Caribbean refresh daily.

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

There is 1 operator available for flights from Oakland Airport to Caribbean as of June 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oakland Airport to Caribbean.

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

The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$223 Cheap Flights from Oakland, California to Caribbean in 2026

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Find the cheapest flights from Oakland, California to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:25 pm - 10:55 am

OAK

SJU

11h 30m

2 stops

5:00 am - 3:00 pm

SJU

OAK

13h 00m

2 stops

$446Southwest

Thu, Aug 27 - Mon, Aug 31

7:40 pm - 11:50 am

OAK

SJU

12h 10m

2 stops

6:05 am - 1:55 pm

SJU

OAK

11h 50m

2 stops

$456Southwest

Sat, Nov 14 - Fri, Nov 20

7:45 pm - 11:00 am

OAK

SJU

12h 15m

2 stops

10:30 am - 7:50 pm

SJU

OAK

12h 20m

2 stops

$486Southwest

Tue, Aug 4 - Tue, Aug 11

8:35 pm - 11:45 am

OAK

SJU

11h 10m

2 stops

5:40 am - 1:45 pm

SJU

OAK

12h 05m

2 stops

$501Southwest

Wed, Dec 2 - Sat, Dec 12

5:00 pm - 11:46 am

OAK

SJU

15h 46m

2 stops

7:00 am - 11:51 pm

SJU

OAK

19h 51m

2 stops

$526Delta

Tue, Aug 18 - Fri, Aug 28

6:50 am - 9:05 pm

OAK

SJU

11h 15m

2 stops

6:00 am - 8:00 pm

SJU

OAK

17h 00m

2 stops

$551Southwest

Tue, Aug 25 - Wed, Aug 26

8:25 pm - 10:55 am

OAK

SJU

11h 30m

2 stops

5:00 am - 3:00 pm

SJU

OAK

13h 00m

2 stops

$556Southwest

Thu, Aug 27 - Mon, Aug 31

5:00 pm - 11:46 am

OAK

SJU

15h 46m

2 stops

7:00 am - 11:51 pm

SJU

OAK

19h 51m

2 stops

$578Delta

Mon, Aug 17 - Tue, Aug 25

5:55 am - 11:30 am

OAK

NAS

26h 35m

2 stops

1:16 pm - 11:56 pm

NAS

OAK

13h 40m

2 stops

$602Delta

Tue, Oct 27 - Tue, Nov 3

1:22 pm - 4:27 pm

OAK

SDQ

24h 05m

2 stops

12:45 pm - 9:44 pm

SDQ

OAK

35h 59m

2 stops

$938Multiple Airlines

Tue, Aug 4 - Wed, Aug 12

Southwest flights from Oakland, California to Caribbean

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

Southwest

Aug 27

OAK8:25 pmOakland

11h 30m

2 stops

SJU10:55 amSan Juan Luis Munoz Marin Intl

Aug 31

SJU5:00 amSan Juan Luis Munoz Marin Intl

13h 00m

2 stops

OAK3:00 pmOakland

$446

Southwest

Nov 14

OAK7:40 pmOakland

12h 10m

2 stops

SJU11:50 amSan Juan Luis Munoz Marin Intl

Nov 20

SJU6:05 amSan Juan Luis Munoz Marin Intl

11h 50m

2 stops

OAK1:55 pmOakland

$456

Southwest

Aug 4

OAK7:45 pmOakland

12h 15m

2 stops

SJU11:00 amSan Juan Luis Munoz Marin Intl

Aug 11

SJU10:30 amSan Juan Luis Munoz Marin Intl

12h 20m

2 stops

OAK7:50 pmOakland

$486

Alaska Airlines flights from Oakland, California to Caribbean

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

Alaska Airlines

Aug 17

OAK8:10 pmOakland

24h 05m

2 stops

SJU11:15 pmSan Juan Luis Munoz Marin Intl

Aug 24

SJU3:44 pmSan Juan Luis Munoz Marin Intl

34h 10m

2 stops

OAK10:54 pmOakland

$866

Alaska Airlines

Aug 16

OAK8:10 pmOakland

24h 05m

2 stops

SJU11:15 pmSan Juan Luis Munoz Marin Intl

Aug 24

SJU3:44 pmSan Juan Luis Munoz Marin Intl

34h 10m

2 stops

OAK10:54 pmOakland

$903

Alaska Airlines

Aug 20

OAK6:04 amOakland

29h 50m

2 stops

SJU2:54 pmSan Juan Luis Munoz Marin Intl

Aug 24

SJU3:44 pmSan Juan Luis Munoz Marin Intl

34h 10m

2 stops

OAK10:54 pmOakland

$949

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 8/27

8:25 pm-10:55 am

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Mon 8/31

5:00 am-3:00 pm

2 stops13h 00m

$446

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 11/14

7:40 pm-11:50 am

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Fri 11/20

6:05 am-1:55 pm

2 stops11h 50m

$456

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 8/4

7:45 pm-11:00 am

2 stops12h 15m

San Juan Luis Munoz Marin Intl

Tue 8/11

10:30 am-7:50 pm

2 stops12h 20m

$486

Quickest round-trip

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 12/2

8:35 pm-11:45 am

2 stops11h 10m

San Juan Luis Munoz Marin Intl

Sat 12/12

5:40 am-1:45 pm

2 stops12h 05m

$501

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 8/18

5:00 pm-11:46 am

2 stops15h 46m

San Juan Luis Munoz Marin Intl

Fri 8/28

7:00 am-11:51 pm

2 stops19h 51m

$526

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 8/25

6:50 am-9:05 pm

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Wed 8/26

6:00 am-8:00 pm

2 stops17h 00m

$551

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 8/27

8:25 pm-10:55 am

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Mon 8/31

5:00 am-3:00 pm

2 stops13h 00m

$556

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 8/17

5:00 pm-11:46 am

2 stops15h 46m

San Juan Luis Munoz Marin Intl

Tue 8/25

7:00 am-11:51 pm

2 stops19h 51m

$578

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 10/27

5:55 am-11:30 am

2 stops26h 35m

Nassau Intl

Tue 11/3

1:16 pm-11:56 pm

2 stops13h 40m

$602

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Tue 8/4

1:22 pm-4:27 pm

2 stops24h 05m

Santo Domingo Las Americas

Wed 8/12

12:45 pm-9:44 pm

2 stops35h 59m

$938

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

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?

In general, August is the cheapest month to fly from Oakland, California to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $360. If you don’t want to visit Caribbean in August, then you should wait until September to fly from Oakland, California, when ticket prices are also cheap, with an average price of $369.

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

You could potentially save up to 26% on your flight if you consider stops on a Oakland, California to Caribbean flight.

Cheap Oakland, California to Caribbean flight deals and tips

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

Fastest flight time	10h 15m
Direct flights	None

The fastest flight from Oakland, California to Caribbean takes 10h 15m

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

Search flight deals

Frequently asked questions about flying from Oakland, California to Caribbean

When did momondo last update prices for flights from Oakland Airport to Caribbean?
Prices for flights from Oakland Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Oakland Airport to Caribbean?
There is 1 operator available for flights from Oakland Airport to Caribbean as of June 2026.
How old do you have to be to fly from Oakland Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oakland Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Oakland, California to Caribbean

Compare and see reviews for airlines that fly from Oakland, California to Caribbean 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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Oakland to Caribbean for you.

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

Yes. momondo enables you to select and highlight flights to Caribbean from Oakland with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oakland to Caribbean.

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

Of course. momondo tracks the price of Oakland to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.