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, 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 49% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 13 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 are 2 operators available for flights from Oakland Airport to Caribbean Islands as of September 2025.

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.

$177 Cheap Flights from Oakland to Caribbean Islands in 2025/26

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Find the cheapest flights from Oakland, California to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

5:00 pm - 11:54 amOAK-NAS

15h 54m2 stops

1:19 pm - 12:03 amNAS-OAK

13h 44m2 stops

$465Delta

Find Deal

Sat, Nov 8 - Tue, Nov 11

7:30 pm - 11:20 amOAK-SJU

11h 50m2 stops

5:40 am - 2:55 pmSJU-OAK

13h 15m2 stops

$481Southwest

Find Deal

Sun, Jan 11 - Wed, Jan 14

7:25 pm - 11:15 amOAK-SJU

11h 50m2 stops

6:10 am - 9:25 pmSJU-OAK

19h 15m2 stops

$499Southwest

Find Deal

Fri, Jan 23 - Sun, Feb 1

5:00 pm - 2:11 pmOAK-MBJ

18h 11m2 stops

4:05 pm - 4:11 pmMBJ-OAK

27h 06m2 stops

$503Delta

Find Deal

Sat, Nov 8 - Sat, Nov 15

4:57 pm - 2:25 pmOAK-PLS

18h 28m2 stops

3:57 pm - 12:30 pmPLS-OAK

23h 33m2 stops

$518Delta

Find Deal

Tue, Dec 23 - Wed, Jan 7

5:40 am - 10:20 pmOAK-SJU

12h 40m2 stops

5:45 am - 2:40 pmSJU-OAK

12h 55m2 stops

$537Southwest

Find Deal

Thu, Nov 13 - Mon, Nov 17

11:30 pm - 9:55 pmOAK-PUJ

18h 25m2 stops

6:15 am - 7:57 pmPUJ-OAK

17h 42m2 stops

$735Multiple Airlines

Find Deal

Thu, Jan 29 - Sun, Feb 1

6:10 am - 11:26 pmOAK-SJU

37h 16m2 stops

7:20 am - 11:38 pmSJU-OAK

20h 18m2 stops

$844Alaska Airlines

Find Deal

Sun, Jan 4 - Wed, Jan 14

1:25 pm - 4:45 pmOAK-PUJ

23h 20m3 stops

6:15 am - 7:57 pmPUJ-OAK

17h 42m2 stops

$846Multiple Airlines

Find Deal

Thu, Jan 29 - Sun, Feb 1

6:30 am - 4:55 amOAK-SJU

18h 25m2 stops

7:20 am - 11:38 pmSJU-OAK

20h 18m2 stops

$859Alaska Airlines

Find Deal

Tue, Mar 3 - Wed, Mar 4

Southwest flights from Oakland, California to Caribbean Islands

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

Southwest

Jan 11

OAK7:30 pmOakland

11h 50m

2 stops

SJU11:20 amSan Juan Luis Munoz Marin Intl

Jan 14

SJU5:40 amSan Juan Luis Munoz Marin Intl

13h 15m

2 stops

OAK2:55 pmOakland

$481

Find similar

Southwest

Jan 23

OAK7:25 pmOakland

11h 50m

2 stops

SJU11:15 amSan Juan Luis Munoz Marin Intl

Feb 1

SJU6:10 amSan Juan Luis Munoz Marin Intl

19h 15m

2 stops

OAK9:25 pmOakland

$499

Find similar

Southwest

Sep 28

OAK7:10 amOakland

14h 25m

2 stops

SJU12:35 amSan Juan Luis Munoz Marin Intl

Oct 1

SJU7:20 amSan Juan Luis Munoz Marin Intl

13h 20m

2 stops

OAK5:40 pmOakland

$529

Find similar

Spirit Airlines flights from Oakland, California to Caribbean Islands

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

Spirit Airlines

Sep 29

OAK6:30 amOakland

28h 41m

3 stops

SJU2:11 pmSan Juan Luis Munoz Marin Intl

Oct 1

SJU6:44 amSan Juan Luis Munoz Marin Intl

19h 48m

2 stops

OAK11:32 pmOakland

$902

Find similar

Spirit Airlines

Sep 29

OAK6:30 amOakland

28h 41m

3 stops

SJU2:11 pmSan Juan Luis Munoz Marin Intl

Oct 1

SJU3:19 pmSan Juan Luis Munoz Marin Intl

35h 13m

3 stops

OAK11:32 pmOakland

$946

Find similar

Spirit Airlines

Sep 28

OAK6:30 amOakland

28h 41m

3 stops

SJU2:11 pmSan Juan Luis Munoz Marin Intl

Oct 1

SJU6:44 amSan Juan Luis Munoz Marin Intl

19h 48m

2 stops

OAK11:32 pmOakland

$987

Find similar

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

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 11/8

5:00 pm-11:54 am

2 stops15h 54m

Nassau Intl

Tue 11/11

1:19 pm-12:03 am

2 stops13h 44m

$465

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 1/11

7:30 pm-11:20 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Wed 1/14

5:40 am-2:55 pm

2 stops13h 15m

$481

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 1/23

7:25 pm-11:15 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Sun 2/1

6:10 am-9:25 pm

2 stops19h 15m

$499

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sat 11/8

5:00 pm-2:11 pm

2 stops18h 11m

Montego Bay Sangster Intl

Sat 11/15

4:05 pm-4:11 pm

2 stops27h 06m

$503

OaklandProvidenciales

OAK - PLS

OAKPLS

Oakland

Tue 12/23

4:57 pm-2:25 pm

2 stops18h 28m

Providenciales

Wed 1/7

3:57 pm-12:30 pm

2 stops23h 33m

$518

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 11/13

5:40 am-10:20 pm

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Mon 11/17

5:45 am-2:40 pm

2 stops12h 55m

$537

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Thu 1/29

11:30 pm-9:55 pm

2 stops18h 25m

Punta Cana

Sun 2/1

6:15 am-7:57 pm

2 stops17h 42m

$735

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 1/4

6:10 am-11:26 pm

2 stops37h 16m

San Juan Luis Munoz Marin Intl

Wed 1/14

7:20 am-11:38 pm

2 stops20h 18m

$844

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Thu 1/29

1:25 pm-4:45 pm

3 stops23h 20m

Punta Cana

Sun 2/1

6:15 am-7:57 pm

2 stops17h 42m

$846

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 3/3

6:30 am-4:55 am

2 stops18h 25m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:20 am-11:38 pm

2 stops20h 18m

$859

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 $298. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $404.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Oakland, California to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $387. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $825. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Oakland, California to Caribbean Islands in the afternoon for as low as $410. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the evening because they tend to be around $535. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Direct flights	None

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 are 2 operators available for flights from Oakland Airport to Caribbean Islands as of September 2025.
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 17.77% of the total bookings. Other popular models include Airbus A320-100/200 with 12.10%, Boeing 737-800 Passenger/BBJ2 (winglets) with 12.06%, and Boeing 737-700 Passenger/BBJ1 (winglets) with 9.65%.

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
Spirit Airlines	PriceFrom $278	Free Cancellation	Rating 6.3 8,042 reviews		Search Spirit Airlines flights
Southwest	PriceFrom $389	Free Cancellation	Rating 8.0 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.

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.

Start using Trips

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Sat 10/25

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Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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Cheap flights from Oakland, California to Caribbean Islands from $177

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Oakland, California to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Southwest flights from Oakland, California to Caribbean Islands

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

Spirit Airlines flights from Oakland, California to Caribbean Islands

Our best Spirit Airlines 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

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

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 $298. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $404.

What is the cheapest day to depart on your flight to Caribbean Islands?

What is the cheapest time of day to depart on your flight to Caribbean Islands?

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?

Delta, Southwest, and Alaska Airlines 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

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