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 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, Delta, and Frontier 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 August 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.

$232 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.

7:50 pm - 10:30 amOAK Oakland-SJU San Juan Luis Munoz Marin Intl

10h 40m2 stops Los Angeles Orlando

6:10 am - 2:20 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

12h 10m2 stops Tampa Los Angeles

$452Southwest

Thu, Nov 12 - Tue, Nov 17

7:45 pm - 10:55 amOAK Oakland-SJU San Juan Luis Munoz Marin Intl

12h 10m2 stops Las Vegas Harry Reid Intl Orlando

6:00 am - 8:05 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

17h 05m2 stops Baltimore/Washington Los Angeles

$470Southwest

Wed, Sep 16 - Wed, Sep 23

8:25 pm - 11:00 amOAK Oakland-SJU San Juan Luis Munoz Marin Intl

11h 35m2 stops Las Vegas Harry Reid Intl Orlando

6:00 am - 8:05 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

17h 05m2 stops Baltimore/Washington Los Angeles

$470Southwest

Mon, Sep 21 - Wed, Sep 30

6:50 pm - 2:05 pmOAK Oakland-SXM Simpson Bay Princess Juliana

16h 15m2 stops Los Angeles Orlando

3:05 pm - 7:15 amSXM Simpson Bay Princess Juliana-OAK Oakland

19h 10m2 stops Orlando Las Vegas Harry Reid Intl

$497Southwest

Sat, Oct 3 - Fri, Oct 9

7:40 pm - 9:10 amOAK Oakland-SJU San Juan Luis Munoz Marin Intl

10h 30m2 stops Denver Intl Orlando

10:30 am - 7:50 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

12h 20m2 stops Orlando Denver Intl

$503Southwest

Thu, Sep 24 - Tue, Sep 29

8:25 pm - 10:50 amOAK Oakland-SJU San Juan Luis Munoz Marin Intl

11h 25m2 stops Las Vegas Harry Reid Intl Orlando

10:30 am - 8:00 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

12h 30m2 stops Orlando Dallas Love Field

$508Southwest

Fri, Sep 25 - Sat, Oct 3

8:25 pm - 10:50 amOAK Oakland-SJU San Juan Luis Munoz Marin Intl

11h 25m2 stops Las Vegas Harry Reid Intl Orlando

8:20 am - 5:20 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

12h 00m2 stops Orlando Las Vegas Harry Reid Intl

$515Southwest

Fri, Aug 28 - Sat, Sep 5

7:40 pm - 9:10 amOAK Oakland-SJU San Juan Luis Munoz Marin Intl

10h 30m2 stops Denver Intl Orlando

6:00 am - 8:05 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

17h 05m2 stops Baltimore/Washington Los Angeles

$515Southwest

Thu, Sep 17 - Wed, Sep 23

5:00 pm - 1:05 pmOAK Oakland-SJU San Juan Luis Munoz Marin Intl

16h 05m2 stops Salt Lake City New York John F Kennedy Intl

3:10 pm - 11:55 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

12h 45m2 stops Detroit Metropolitan Wayne County Salt Lake City

$526Delta

Mon, Nov 16 - Fri, Dec 4

5:00 pm - 1:05 pmOAK Oakland-SJU San Juan Luis Munoz Marin Intl

16h 05m2 stops Salt Lake City New York John F Kennedy Intl

2:05 pm - 11:55 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

13h 50m2 stops New York John F Kennedy Intl Salt Lake City

$526Delta

Mon, Nov 16 - Thu, Dec 3

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 1:01 pmOAK Oakland-MBJ Montego Bay Sangster Intl

29h 01m2 stops Salt Lake City Atlanta Hartsfield-Jackson

2:26 pm - 11:52 amMBJ Montego Bay Sangster Intl-OAK Oakland

23h 26m2 stops Atlanta Hartsfield-Jackson Salt Lake City

$1,166Delta

Sat, Aug 15 - Sat, Aug 22

6:00 am - 1:01 pmOAK Oakland-MBJ Montego Bay Sangster Intl

29h 01m2 stops Salt Lake City Atlanta Hartsfield-Jackson

4:59 pm - 11:56 pmMBJ Montego Bay Sangster Intl-OAK Oakland

32h 57m2 stops Atlanta Hartsfield-Jackson Salt Lake City

$1,302Delta

Sat, Aug 15 - Sun, Aug 23

6:00 am - 11:44 amOAK Oakland-MBJ Montego Bay Sangster Intl

27h 44m2 stops Salt Lake City Atlanta Hartsfield-Jackson

4:59 pm - 4:14 pmMBJ Montego Bay Sangster Intl-OAK Oakland

25h 15m2 stops Atlanta Hartsfield-Jackson Salt Lake City

$1,329Delta

Tue, Aug 18 - Fri, Aug 21

6:00 am - 1:01 pmOAK Oakland-MBJ Montego Bay Sangster Intl

29h 01m2 stops Salt Lake City Atlanta Hartsfield-Jackson

12:59 pm - 11:56 pmMBJ Montego Bay Sangster Intl-OAK Oakland

36h 57m2 stops New York John F Kennedy Intl Salt Lake City

$1,355Delta

Sat, Aug 15 - Tue, Aug 25

8:10 pm - 10:54 pmOAK Oakland-SJU San Juan Luis Munoz Marin Intl

23h 44m2 stops San Diego Chicago O'Hare Intl

12:55 am - 7:52 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

21h 57m2 stops Chicago O'Hare Intl San Diego

$1,356Alaska Airlines

Fri, Aug 14 - Fri, Aug 21

5:00 pm - 3:34 pmOAK Oakland-MBJ Montego Bay Sangster Intl

20h 34m2 stops Salt Lake City Atlanta Hartsfield-Jackson

2:26 pm - 11:56 pmMBJ Montego Bay Sangster Intl-OAK Oakland

35h 30m2 stops Atlanta Hartsfield-Jackson Salt Lake City

$1,357Delta

Sat, Aug 15 - Wed, Aug 26

8:10 pm - 10:54 pmOAK Oakland-SJU San Juan Luis Munoz Marin Intl

23h 44m2 stops San Diego Chicago O'Hare Intl

12:55 am - 7:52 pmSJU San Juan Luis Munoz Marin Intl-OAK Oakland

21h 57m2 stops Chicago O'Hare Intl San Diego

$1,407Alaska Airlines

Fri, Aug 14 - Fri, Aug 21

6:00 am - 11:44 amOAK Oakland-MBJ Montego Bay Sangster Intl

27h 44m2 stops Salt Lake City Atlanta Hartsfield-Jackson

4:59 pm - 11:56 pmMBJ Montego Bay Sangster Intl-OAK Oakland

32h 57m2 stops Atlanta Hartsfield-Jackson Salt Lake City

$1,465Delta

Tue, Aug 18 - Sun, Aug 23

6:00 am - 11:44 amOAK Oakland-MBJ Montego Bay Sangster Intl

27h 44m2 stops Salt Lake City Atlanta Hartsfield-Jackson

12:59 pm - 11:56 pmMBJ Montego Bay Sangster Intl-OAK Oakland

36h 57m2 stops New York John F Kennedy Intl Salt Lake City

$1,518Delta

Tue, Aug 18 - Tue, Aug 25

6:00 am - 11:34 amOAK Oakland-MBJ Montego Bay Sangster Intl

27h 34m2 stops Salt Lake City New York John F Kennedy Intl

2:26 pm - 11:56 pmMBJ Montego Bay Sangster Intl-OAK Oakland

35h 30m2 stops Atlanta Hartsfield-Jackson Salt Lake City

$1,520Delta

Tue, Aug 18 - Wed, Aug 26

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Southwest flights from Oakland, California to Caribbean Islands

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

Southwest

Nov 12

OAK7:50 pmOakland

10h 40m

2 stops

SJU10:30 amSan Juan Luis Munoz Marin Intl

Nov 17

SJU6:10 amSan Juan Luis Munoz Marin Intl

12h 10m

2 stops

OAK2:20 pmOakland

$452

Southwest

Sep 16

OAK7:45 pmOakland

12h 10m

2 stops

SJU10:55 amSan Juan Luis Munoz Marin Intl

Sep 23

SJU6:00 amSan Juan Luis Munoz Marin Intl

17h 05m

2 stops

OAK8:05 pmOakland

$470

Southwest

Oct 3

OAK6:50 pmOakland

16h 15m

2 stops

SXM2:05 pmSimpson Bay Princess Juliana

Oct 9

SXM3:05 pmSimpson Bay Princess Juliana

19h 10m

2 stops

OAK7:15 amOakland

$497

Delta flights from Oakland, California to Caribbean Islands

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

Delta

Nov 16

OAK5:00 pmOakland

16h 05m

2 stops

SJU1:05 pmSan Juan Luis Munoz Marin Intl

Dec 2

SJU3:10 pmSan Juan Luis Munoz Marin Intl

12h 45m

2 stops

OAK11:55 pmOakland

$526

Delta

Nov 15

OAK5:00 pmOakland

16h 05m

2 stops

SJU1:05 pmSan Juan Luis Munoz Marin Intl

Dec 3

SJU2:05 pmSan Juan Luis Munoz Marin Intl

13h 50m

2 stops

OAK11:55 pmOakland

$601

Delta

Jan 20

OAK5:55 amOakland

13h 55m

2 stops

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Jan 26

SJU3:15 pmSan Juan Luis Munoz Marin Intl

12h 41m

2 stops

OAK11:56 pmOakland

$853

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

Quickest round-trip

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Thu 11/12

7:50 pm-10:30 am

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Tue 11/17

6:10 am-2:20 pm

2 stops12h 10m

$452

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Wed 9/16

7:45 pm-10:55 am

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Wed 9/23

6:00 am-8:05 pm

2 stops17h 05m

$470

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Mon 9/21

8:25 pm-11:00 am

2 stops11h 35m

San Juan Luis Munoz Marin Intl

Wed 9/30

6:00 am-8:05 pm

2 stops17h 05m

$470

OaklandSimpson Bay

OAK Oakland - SXM Simpson Bay Princess Juliana

OAKSXM

Oakland

Sat 10/3

6:50 pm-2:05 pm

2 stops16h 15m

Simpson Bay Princess Juliana

Fri 10/9

3:05 pm-7:15 am

2 stops19h 10m

$497

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Thu 9/24

7:40 pm-9:10 am

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Tue 9/29

10:30 am-7:50 pm

2 stops12h 20m

$503

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Fri 9/25

8:25 pm-10:50 am

2 stops11h 25m

San Juan Luis Munoz Marin Intl

Sat 10/3

10:30 am-8:00 pm

2 stops12h 30m

$508

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Fri 8/28

8:25 pm-10:50 am

2 stops11h 25m

San Juan Luis Munoz Marin Intl

Sat 9/5

8:20 am-5:20 pm

2 stops12h 00m

$515

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Thu 9/17

7:40 pm-9:10 am

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Wed 9/23

6:00 am-8:05 pm

2 stops17h 05m

$515

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Mon 11/16

5:00 pm-1:05 pm

2 stops16h 05m

San Juan Luis Munoz Marin Intl

Fri 12/4

3:10 pm-11:55 pm

2 stops12h 45m

$526

OaklandSan Juan

OAK Oakland - SJU San Juan Luis Munoz Marin Intl

OAKSJU

Oakland

Mon 11/16

5:00 pm-1:05 pm

2 stops16h 05m

San Juan Luis Munoz Marin Intl

Thu 12/3

2:05 pm-11:55 pm

2 stops13h 50m

$526

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 30m
Direct flights	None

The fastest flight from Oakland, California to Caribbean Islands takes 10h 30m

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 August 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 22.52% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 20.82%, Airbus A320neo with 12.80%, and Airbus A321neo with 10.20%.

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 $412	Free Cancellation	Rating 8.0 4,218 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.