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

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

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 40% 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 May 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.

$229 Cheap Flights from Oakland, California to Caribbean Islands in 2026

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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 - 10:55 am

OAK

SJU

12h 15m

2 stops

10:30 am - 8:00 pm

SJU

OAK

12h 30m

2 stops

$446Southwest

Sun, Aug 30 - Wed, Sep 16

7:40 pm - 10:55 am

OAK

SJU

12h 15m

2 stops

5:15 am - 1:55 pm

SJU

OAK

11h 40m

2 stops

$458Southwest

Sun, Aug 30 - Wed, Sep 16

7:40 pm - 9:10 am

OAK

SJU

10h 30m

2 stops

5:05 am - 1:40 pm

SJU

OAK

11h 35m

2 stops

$470Southwest

Sun, Aug 9 - Sat, Aug 15

8:05 am - 11:35 pm

OAK

SJU

12h 30m

2 stops

5:30 am - 2:50 pm

SJU

OAK

12h 20m

2 stops

$569Southwest

Sun, Oct 18 - Sun, Oct 25

8:30 pm - 11:10 am

OAK

SJU

11h 40m

2 stops

5:30 am - 2:45 pm

SJU

OAK

12h 15m

2 stops

$593Southwest

Wed, Oct 14 - Sun, Oct 18

7:35 pm - 1:15 pm

OAK

NAS

14h 40m

2 stops

2:10 pm - 10:15 pm

NAS

OAK

11h 05m

2 stops

$606Southwest

Tue, Jun 2 - Tue, Jun 9

6:00 am - 11:51 am

OAK

NAS

26h 51m

2 stops

1:16 pm - 11:50 pm

NAS

OAK

13h 34m

2 stops

$611Delta

Mon, Jul 6 - Tue, Jul 14

4:57 pm - 11:51 am

OAK

NAS

15h 54m

2 stops

1:09 pm - 11:51 pm

NAS

OAK

13h 42m

2 stops

$622Delta

Mon, Aug 17 - Tue, Aug 25

4:57 pm - 11:56 am

OAK

SJU

15h 59m

2 stops

7:30 am - 11:49 pm

SJU

OAK

19h 19m

2 stops

$630Delta

Sun, Aug 30 - Wed, Sep 16

8:22 pm - 6:38 pm

OAK

PUJ

19h 16m

2 stops

9:18 am - 9:44 pm

PUJ

OAK

15h 26m

2 stops

$699Multiple Airlines

Sat, Jun 20 - Sat, Jun 27

Alaska Airlines flights from Oakland, California to Caribbean Islands

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

Alaska Airlines

Aug 18

OAK8:10 pmOakland

23h 57m

2 stops

SJU11:07 pmSan Juan Luis Munoz Marin Intl

Aug 21

SJU3:44 pmSan Juan Luis Munoz Marin Intl

30h 11m

2 stops

OAK6:55 pmOakland

$1,023

Alaska Airlines

Aug 24

OAK10:05 amOakland

25h 49m

2 stops

SJU2:54 pmSan Juan Luis Munoz Marin Intl

Aug 26

SJU3:44 pmSan Juan Luis Munoz Marin Intl

24h 29m

2 stops

OAK1:13 pmOakland

$1,035

Alaska Airlines

Aug 24

OAK2:09 pmOakland

21h 45m

2 stops

SJU2:54 pmSan Juan Luis Munoz Marin Intl

Aug 26

SJU3:44 pmSan Juan Luis Munoz Marin Intl

24h 29m

2 stops

OAK1:13 pmOakland

$1,044

Southwest flights from Oakland, California to Caribbean Islands

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

Southwest

Aug 30

OAK7:40 pmOakland

12h 15m

2 stops

SJU10:55 amSan Juan Luis Munoz Marin Intl

Sep 16

SJU10:30 amSan Juan Luis Munoz Marin Intl

12h 30m

2 stops

OAK8:00 pmOakland

$446

Southwest

Aug 30

OAK7:40 pmOakland

12h 15m

2 stops

SJU10:55 amSan Juan Luis Munoz Marin Intl

Sep 16

SJU5:15 amSan Juan Luis Munoz Marin Intl

11h 40m

2 stops

OAK1:55 pmOakland

$458

Southwest

Aug 9

OAK7:40 pmOakland

10h 30m

2 stops

SJU9:10 amSan Juan Luis Munoz Marin Intl

Aug 15

SJU5:05 amSan Juan Luis Munoz Marin Intl

11h 35m

2 stops

OAK1:40 pmOakland

$470

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

Sun 8/30

7:40 pm-10:55 am

2 stops12h 15m

San Juan Luis Munoz Marin Intl

Wed 9/16

10:30 am-8:00 pm

2 stops12h 30m

$446

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 8/30

7:40 pm-10:55 am

2 stops12h 15m

San Juan Luis Munoz Marin Intl

Wed 9/16

5:15 am-1:55 pm

2 stops11h 40m

$458

Quickest round-trip

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 8/9

7:40 pm-9:10 am

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Sat 8/15

5:05 am-1:40 pm

2 stops11h 35m

$470

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 10/18

8:05 am-11:35 pm

2 stops12h 30m

San Juan Luis Munoz Marin Intl

Sun 10/25

5:30 am-2:50 pm

2 stops12h 20m

$569

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 10/14

8:30 pm-11:10 am

2 stops11h 40m

San Juan Luis Munoz Marin Intl

Sun 10/18

5:30 am-2:45 pm

2 stops12h 15m

$593

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Tue 6/2

7:35 pm-1:15 pm

2 stops14h 40m

Nassau Intl

Tue 6/9

2:10 pm-10:15 pm

2 stops11h 05m

$606

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Mon 7/6

6:00 am-11:51 am

2 stops26h 51m

Nassau Intl

Tue 7/14

1:16 pm-11:50 pm

2 stops13h 34m

$611

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Mon 8/17

4:57 pm-11:51 am

2 stops15h 54m

Nassau Intl

Tue 8/25

1:09 pm-11:51 pm

2 stops13h 42m

$622

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 8/30

4:57 pm-11:56 am

2 stops15h 59m

San Juan Luis Munoz Marin Intl

Wed 9/16

7:30 am-11:49 pm

2 stops19h 19m

$630

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Sat 6/20

8:22 pm-6:38 pm

2 stops19h 16m

Punta Cana

Sat 6/27

9:18 am-9:44 pm

2 stops15h 26m

$699

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	11h 00m
Direct flights	None

The fastest flight from Oakland, California to Caribbean Islands takes 11h 00m

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 May 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 28.08% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 19.69%, Airbus A320neo with 9.66%, and Airbus A321-100/200 with 5.85%.

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 4,304 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.