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

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

What airlines fly to Caribbean Islands?

American Airlines, United Airlines and JetBlue 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 42% 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.

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 February 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.

$278 Cheap Flights from Oakland to Caribbean Islands in 2026

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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.

7:35 pm - 9:15 am

OAK

SJU

10h 40m

2 stops

2:00 pm - 11:55 pm

SJU

OAK

12h 55m

2 stops

$428Southwest

Thu, Apr 2 - Thu, Apr 9

5:10 am - 9:40 pm

OAK

SJU

12h 30m

2 stops

10:20 am - 7:50 pm

SJU

OAK

13h 30m

2 stops

$436Southwest

Sat, Feb 21 - Wed, Feb 25

5:55 am - 11:48 am

OAK

NAS

26h 53m

2 stops

5:58 pm - 9:41 pm

NAS

OAK

30h 43m

2 stops

$448Delta

Sun, Apr 19 - Fri, Apr 24

11:55 pm - 1:20 pm

OAK

SJU

10h 25m

1 stop

11:25 am - 10:05 pm

SJU

OAK

13h 40m

2 stops

$453Southwest

Fri, May 1 - Tue, May 5

6:05 am - 12:45 am

OAK

SJU

15h 40m

2 stops

10:20 pm - 10:25 am

SJU

OAK

15h 05m

2 stops

$461Southwest

Wed, Jun 24 - Mon, Jun 29

6:05 am - 8:00 pm

OAK

SJU

10h 55m

2 stops

11:25 am - 10:05 pm

SJU

OAK

13h 40m

2 stops

$481Southwest

Fri, May 1 - Tue, May 5

8:55 pm - 1:15 pm

OAK

NAS

13h 20m

2 stops

2:10 pm - 9:55 pm

NAS

OAK

10h 45m

2 stops

$487Southwest

Thu, May 14 - Wed, May 20

12:40 pm - 12:26 pm

OAK

NAS

20h 46m

2 stops

1:15 pm - 11:51 pm

NAS

OAK

13h 36m

2 stops

$704Delta

Mon, Feb 23 - Mon, Mar 2

12:30 pm - 4:41 pm

OAK

PUJ

25h 11m

3 stops

2:20 pm - 11:45 am

PUJ

OAK

24h 25m

2 stops

$842Multiple Airlines

Wed, Mar 18 - Wed, Mar 25

12:35 pm - 12:42 pm

OAK

MBJ

22h 07m

2 stops

2:42 pm - 9:43 pm

MBJ

OAK

33h 01m

2 stops

$943Delta

Sat, Apr 4 - Fri, Apr 10

Delta flights from Oakland, California to Caribbean Islands

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

Delta

Apr 19

OAK5:55 amOakland

26h 53m

2 stops

NAS11:48 amNassau Intl

Apr 24

NAS5:58 pmNassau Intl

30h 43m

2 stops

OAK9:41 pmOakland

$448

Delta

Feb 23

OAK12:40 pmOakland

20h 46m

2 stops

NAS12:26 pmNassau Intl

Mar 2

NAS1:15 pmNassau Intl

13h 36m

2 stops

OAK11:51 pmOakland

$704

Delta

Apr 4

OAK12:35 pmOakland

22h 07m

2 stops

MBJ12:42 pmMontego Bay Sangster Intl

Apr 10

MBJ2:42 pmMontego Bay Sangster Intl

33h 01m

2 stops

OAK9:43 pmOakland

$943

Southwest flights from Oakland, California to Caribbean Islands

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

Southwest

Apr 2

OAK7:35 pmOakland

10h 40m

2 stops

SJU9:15 amSan Juan Luis Munoz Marin Intl

Apr 9

SJU2:00 pmSan Juan Luis Munoz Marin Intl

12h 55m

2 stops

OAK11:55 pmOakland

$428

Southwest

Feb 21

OAK5:10 amOakland

12h 30m

2 stops

SJU9:40 pmSan Juan Luis Munoz Marin Intl

Feb 25

SJU10:20 amSan Juan Luis Munoz Marin Intl

13h 30m

2 stops

OAK7:50 pmOakland

$436

Southwest

May 1

OAK11:55 pmOakland

10h 25m

1 stop

SJU1:20 pmSan Juan Luis Munoz Marin Intl

May 5

SJU11:25 amSan Juan Luis Munoz Marin Intl

13h 40m

2 stops

OAK10:05 pmOakland

$453

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

Thu 4/2

7:35 pm-9:15 am

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Thu 4/9

2:00 pm-11:55 pm

2 stops12h 55m

$428

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 2/21

5:10 am-9:40 pm

2 stops12h 30m

San Juan Luis Munoz Marin Intl

Wed 2/25

10:20 am-7:50 pm

2 stops13h 30m

$436

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sun 4/19

5:55 am-11:48 am

2 stops26h 53m

Nassau Intl

Fri 4/24

5:58 pm-9:41 pm

2 stops30h 43m

$448

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/1

11:55 pm-1:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Tue 5/5

11:25 am-10:05 pm

2 stops13h 40m

$453

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 6/24

6:05 am-12:45 am

2 stops15h 40m

San Juan Luis Munoz Marin Intl

Mon 6/29

10:20 pm-10:25 am

2 stops15h 05m

$461

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/1

6:05 am-8:00 pm

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Tue 5/5

11:25 am-10:05 pm

2 stops13h 40m

$481

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Thu 5/14

8:55 pm-1:15 pm

2 stops13h 20m

Nassau Intl

Wed 5/20

2:10 pm-9:55 pm

2 stops10h 45m

$487

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Mon 2/23

12:40 pm-12:26 pm

2 stops20h 46m

Nassau Intl

Mon 3/2

1:15 pm-11:51 pm

2 stops13h 36m

$704

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Wed 3/18

12:30 pm-4:41 pm

3 stops25h 11m

Punta Cana

Wed 3/25

2:20 pm-11:45 am

2 stops24h 25m

$842

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sat 4/4

12:35 pm-12:42 pm

2 stops22h 07m

Montego Bay Sangster Intl

Fri 4/10

2:42 pm-9:43 pm

2 stops33h 01m

$943

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 March is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $470.

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	9h 45m
Direct flights	None

The fastest flight from Oakland, California to Caribbean Islands takes 9h 45m

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 February 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 24.03% of the total bookings. Other popular models include Airbus A320-100/200 with 11.86%, Boeing 737-800 Passenger/BBJ2 (winglets) with 11.40%, and Airbus A320neo with 11.32%.

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 8.0 4,272 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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Cheap flights from Oakland, California to Caribbean Islands from $250

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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

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Find the cheapest flights from Oakland, California to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

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Delta flights from Oakland, California to Caribbean Islands

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

Southwest flights from Oakland, California to Caribbean Islands

Our best Southwest 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 March is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $470.

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, Alaska Airlines, and Delta 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