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

Spirit Airlines, Southwest, and Delta 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 51% 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 August 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.

$139 Cheap Flights from Oakland to Caribbean Islands in 2025

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Find the cheapest flights from Oakland, California to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

2:39 pm - 1:43 pmOAK-SJU

20h 04m2 stops

10:42 am - 11:32 pmSJU-OAK

15h 50m2 stops

$322Spirit Airlines

Find Deal

Wed, Oct 1 - Mon, Oct 6

6:30 am - 8:56 pmOAK-SJU

35h 26m3 stops

10:42 am - 11:32 pmSJU-OAK

15h 50m2 stops

$353Spirit Airlines

Find Deal

Mon, Sep 29 - Mon, Oct 6

2:39 pm - 9:44 amOAK-STT

16h 05m2 stops

10:49 am - 11:32 pmSTT-OAK

15h 43m2 stops

$367Spirit Airlines

Find Deal

Thu, Sep 4 - Tue, Sep 9

5:00 pm - 11:36 amOAK-SJU

15h 36m2 stops

7:15 am - 9:32 pmSJU-OAK

17h 17m2 stops

$369Delta

Find Deal

Sat, Oct 25 - Sat, Nov 1

6:30 am - 8:56 pmOAK-SJU

35h 26m3 stops

11:59 am - 11:32 pmSJU-OAK

38h 33m3 stops

$371Spirit Airlines

Find Deal

Mon, Sep 29 - Mon, Oct 6

7:45 pm - 11:00 amOAK-SJU

11h 15m2 stops

3:50 pm - 1:30 amSJU-OAK

13h 40m1 stop

$415Southwest

Find Deal

Thu, Nov 13 - Sat, Nov 22

5:00 pm - 11:36 amOAK-SJU

15h 36m2 stops

7:15 am - 9:32 pmSJU-OAK

17h 17m2 stops

$449Delta

Find Deal

Sat, Oct 25 - Sat, Nov 1

5:25 am - 7:25 pmOAK-SJU

11h 00m2 stops

7:40 am - 6:50 pmSJU-OAK

14h 10m2 stops

$479Southwest

Find Deal

Fri, Oct 10 - Tue, Oct 14

6:00 am - 3:11 pmOAK-SJU

30h 11m2 stops

3:19 pm - 11:32 pmSJU-OAK

35h 13m3 stops

$506

Find Deal

Fri, Oct 10 - Tue, Oct 14

6:30 am - 2:34 amOAK-SJU

17h 04m2 stops

3:39 am - 11:32 pmSJU-OAK

22h 53m2 stops

$525

Find Deal

Thu, Sep 18 - Mon, Sep 22

Spirit Airlines flights from Oakland, California to Caribbean Islands

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

Spirit Airlines

Oct 1

OAK2:39 pmOakland

20h 04m

2 stops

SJU1:43 pmSan Juan Luis Munoz Marin Intl

Oct 6

SJU10:42 amSan Juan Luis Munoz Marin Intl

15h 50m

2 stops

OAK11:32 pmOakland

$322

Find similar

Spirit Airlines

Sep 29

OAK6:30 amOakland

35h 26m

3 stops

SJU8:56 pmSan Juan Luis Munoz Marin Intl

Oct 6

SJU10:42 amSan Juan Luis Munoz Marin Intl

15h 50m

2 stops

OAK11:32 pmOakland

$353

Find similar

Spirit Airlines

Sep 4

OAK2:39 pmOakland

16h 05m

2 stops

STT9:44 amSaint Thomas Island Cyril E King

Sep 9

STT10:49 amSaint Thomas Island Cyril E King

15h 43m

2 stops

OAK11:32 pmOakland

$367

Find similar

Delta flights from Oakland, California to Caribbean Islands

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

Delta

Oct 25

OAK5:00 pmOakland

15h 36m

2 stops

SJU11:36 amSan Juan Luis Munoz Marin Intl

Nov 1

SJU7:15 amSan Juan Luis Munoz Marin Intl

17h 17m

2 stops

OAK9:32 pmOakland

$369

Find similar

Delta

Oct 25

OAK5:00 pmOakland

15h 36m

2 stops

SJU11:36 amSan Juan Luis Munoz Marin Intl

Nov 1

SJU7:15 amSan Juan Luis Munoz Marin Intl

17h 17m

2 stops

OAK9:32 pmOakland

$449

Find similar

Delta

Jan 28

OAK1:15 pmOakland

20h 30m

2 stops

MBJ12:45 pmMontego Bay Sangster Intl

Feb 2

MBJ2:10 pmMontego Bay Sangster Intl

12h 43m

2 stops

OAK11:53 pmOakland

$582

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

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 10/1

2:39 pm-1:43 pm

2 stops20h 04m

San Juan Luis Munoz Marin Intl

Mon 10/6

10:42 am-11:32 pm

2 stops15h 50m

$322

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 9/29

6:30 am-8:56 pm

3 stops35h 26m

San Juan Luis Munoz Marin Intl

Mon 10/6

10:42 am-11:32 pm

2 stops15h 50m

$353

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Thu 9/4

2:39 pm-9:44 am

2 stops16h 05m

Saint Thomas Island Cyril E King

Tue 9/9

10:49 am-11:32 pm

2 stops15h 43m

$367

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 10/25

5:00 pm-11:36 am

2 stops15h 36m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:15 am-9:32 pm

2 stops17h 17m

$369

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 9/29

6:30 am-8:56 pm

3 stops35h 26m

San Juan Luis Munoz Marin Intl

Mon 10/6

11:59 am-11:32 pm

3 stops38h 33m

$371

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 11/13

7:45 pm-11:00 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Sat 11/22

3:50 pm-1:30 am

1 stop13h 40m

$415

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 10/25

5:00 pm-11:36 am

2 stops15h 36m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:15 am-9:32 pm

2 stops17h 17m

$449

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 10/10

5:25 am-7:25 pm

2 stops11h 00m

San Juan Luis Munoz Marin Intl

Tue 10/14

7:40 am-6:50 pm

2 stops14h 10m

$479

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 10/10

6:00 am-3:11 pm

2 stops30h 11m

San Juan Luis Munoz Marin Intl

Tue 10/14

3:19 pm-11:32 pm

3 stops35h 13m

$506

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 9/18

6:30 am-2:34 am

2 stops17h 04m

San Juan Luis Munoz Marin Intl

Mon 9/22

3:39 am-11:32 pm

2 stops22h 53m

$525

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 September is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $442.

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

Best Price Found	$139
Fastest flight time	11h 00m
Direct flights	None
Airports in Caribbean Islands	8 airports

The best one-way flight to Caribbean Islands from Oakland, California in the past 72 hours is $139. The best round-trip flight deal from Oakland, California to Caribbean Islands found on momondo in the last 72 hours is $322.

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

There are no direct flights from Oakland, California to Caribbean Islands. Popular non-direct routes for this connection are Oakland Airport - Nassau Intl Airport, Oakland Airport - San Juan Luis Munoz Marin Intl Airport and Oakland Airport - Montego Bay Sangster Intl Airport.

There are 8 airports near Caribbean Islands: Nassau Intl (NAS), Kingston Norman Manley (KIN), Saint Thomas Island Cyril E King (STT), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), Simpson Bay Princess Juliana (SXM), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)

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 August 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 16.88% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 14.35%, Boeing 737-700 Passenger/BBJ1 (winglets) with 10.71%, and Airbus A320neo with 10.62%.

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 $260	Free Cancellation	Rating 6.3 8,048 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.

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Popular cities in Caribbean Islands

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Cheap flights from Oakland, California to Caribbean Islands from $139

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

Spirit Airlines flights from Oakland, California to Caribbean Islands

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

Delta flights from Oakland, California to Caribbean Islands

Our best Delta 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 September is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $442.

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?

Spirit Airlines, Southwest, 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

Best Price Found

Fastest flight time

Direct flights

Airports in Caribbean Islands

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