What airlines fly to Caribbean?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Caribbean from Oakland, California according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 13 different airlines that fly to Caribbean 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?

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

When did momondo last update prices for flights from Oakland Airport to Caribbean?

Prices for flights from Oakland Airport to Caribbean refresh daily.

How many operators does momondo search for flights from Oakland Airport to Caribbean?

There are 2 operators available for flights from Oakland Airport to Caribbean as of August 2025.

How old do you have to be to fly from Oakland Airport to Caribbean?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oakland Airport to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$180 Cheap Flights from Oakland to Caribbean in 2025

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Find the cheapest flights from Oakland, California to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

12:15 pm - 8:44 pmOAK-SJU

28h 29m2 stops

6:00 am - 4:15 pmSJU-OAK

14h 15m2 stops

$365Spirit Airlines

Find Deal

Sat, Nov 8 - Mon, Nov 10

12:15 pm - 4:23 pmOAK-SJU

24h 08m2 stops

6:00 am - 4:15 pmSJU-OAK

14h 15m2 stops

$371Spirit Airlines

Find Deal

Thu, Nov 6 - Mon, Nov 10

5:11 pm - 1:00 pmOAK-SJU

15h 49m2 stops

6:00 am - 4:16 pmSJU-OAK

38h 16m2 stops

$377Spirit Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

7:10 pm - 10:50 amOAK-SJU

12h 40m2 stops

7:20 am - 5:40 pmSJU-OAK

13h 20m2 stops

$390Southwest

Find Deal

Tue, Sep 16 - Tue, Sep 23

4:30 pm - 9:05 amOAK-SJU

13h 35m2 stops

5:40 am - 2:30 pmSJU-OAK

12h 50m2 stops

$465Southwest

Find Deal

Sun, Oct 26 - Sun, Nov 2

2:39 pm - 2:14 pmOAK-PUJ

20h 35m2 stops

2:36 pm - 7:49 amPUJ-OAK

20h 13m2 stops

$475

Find Deal

Mon, Sep 29 - Mon, Oct 6

7:19 pm - 9:30 amOAK-SDQ

35h 11m3 stops

5:05 pm - 1:34 pmSDQ-OAK

23h 29m3 stops

$514

Find Deal

Sun, Sep 14 - Sun, Sep 21

1:15 pm - 3:15 pmOAK-AUA

22h 00m2 stops

4:30 pm - 12:24 pmAUA-OAK

23h 54m2 stops

$798Delta

Find Deal

Sun, Nov 16 - Thu, Nov 20

12:35 pm - 11:48 amOAK-NAS

20h 13m2 stops

3:00 pm - 10:46 pmNAS-OAK

10h 46m2 stops

$824Delta

Find Deal

Sat, Aug 30 - Fri, Sep 5

2:31 pm - 2:53 pmOAK-SJU

20h 22m2 stops

8:09 am - 11:59 pmSJU-OAK

19h 50m2 stops

$1,530Alaska Airlines

Find Deal

Fri, Dec 12 - Wed, Dec 17

Spirit Airlines flights from Oakland, California to Caribbean

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

Spirit Airlines

Nov 8

OAK12:15 pmOakland

28h 29m

2 stops

SJU8:44 pmSan Juan Luis Munoz Marin Intl

Nov 10

SJU6:00 amSan Juan Luis Munoz Marin Intl

14h 15m

2 stops

OAK4:15 pmOakland

$365

Find similar

Spirit Airlines

Nov 6

OAK12:15 pmOakland

24h 08m

2 stops

SJU4:23 pmSan Juan Luis Munoz Marin Intl

Nov 10

SJU6:00 amSan Juan Luis Munoz Marin Intl

14h 15m

2 stops

OAK4:15 pmOakland

$371

Find similar

Spirit Airlines

Dec 4

OAK5:11 pmOakland

15h 49m

2 stops

SJU1:00 pmSan Juan Luis Munoz Marin Intl

Dec 8

SJU6:00 amSan Juan Luis Munoz Marin Intl

38h 16m

2 stops

OAK4:16 pmOakland

$377

Find similar

Southwest flights from Oakland, California to Caribbean

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

Southwest

Sep 16

OAK7:10 pmOakland

12h 40m

2 stops

SJU10:50 amSan Juan Luis Munoz Marin Intl

Sep 23

SJU7:20 amSan Juan Luis Munoz Marin Intl

13h 20m

2 stops

OAK5:40 pmOakland

$390

Find similar

Southwest

Oct 26

OAK4:30 pmOakland

13h 35m

2 stops

SJU9:05 amSan Juan Luis Munoz Marin Intl

Nov 2

SJU5:40 amSan Juan Luis Munoz Marin Intl

12h 50m

2 stops

OAK2:30 pmOakland

$465

Find similar

Southwest

Nov 18

OAK8:25 pmOakland

14h 35m

2 stops

AUA3:00 pmOranjestad Reina Beatrix

Nov 22

AUA2:40 pmOranjestad Reina Beatrix

13h 55m

2 stops

OAK12:35 amOakland

$604

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Oakland, California to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 11/8

12:15 pm-8:44 pm

2 stops28h 29m

San Juan Luis Munoz Marin Intl

Mon 11/10

6:00 am-4:15 pm

2 stops14h 15m

$365

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 11/6

12:15 pm-4:23 pm

2 stops24h 08m

San Juan Luis Munoz Marin Intl

Mon 11/10

6:00 am-4:15 pm

2 stops14h 15m

$371

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 12/4

5:11 pm-1:00 pm

2 stops15h 49m

San Juan Luis Munoz Marin Intl

Mon 12/8

6:00 am-4:16 pm

2 stops38h 16m

$377

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 9/16

7:10 pm-10:50 am

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Tue 9/23

7:20 am-5:40 pm

2 stops13h 20m

$390

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 10/26

4:30 pm-9:05 am

2 stops13h 35m

San Juan Luis Munoz Marin Intl

Sun 11/2

5:40 am-2:30 pm

2 stops12h 50m

$465

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Mon 9/29

2:39 pm-2:14 pm

2 stops20h 35m

Punta Cana

Mon 10/6

2:36 pm-7:49 am

2 stops20h 13m

$475

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Sun 9/14

7:19 pm-9:30 am

3 stops35h 11m

Santo Domingo Las Americas

Sun 9/21

5:05 pm-1:34 pm

3 stops23h 29m

$514

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Sun 11/16

1:15 pm-3:15 pm

2 stops22h 00m

Oranjestad Reina Beatrix

Thu 11/20

4:30 pm-12:24 pm

2 stops23h 54m

$798

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Sat 8/30

12:35 pm-11:48 am

2 stops20h 13m

Nassau Intl

Fri 9/5

3:00 pm-10:46 pm

2 stops10h 46m

$824

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 12/12

2:31 pm-2:53 pm

2 stops20h 22m

San Juan Luis Munoz Marin Intl

Wed 12/17

8:09 am-11:59 pm

2 stops19h 50m

$1,530

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

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?

In general, October is the cheapest month to fly from Oakland, California to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $298. If you don’t want to visit Caribbean in October, then you should wait until September to fly from Oakland, California, when ticket prices are also cheap, with an average price of $442.

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

The cheapest day to depart from Oakland, California to Caribbean is on a Tuesday when prices can be found 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.

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

In the afternoon is the cheapest time of day to fly from Oakland, California to Caribbean when you can find flight prices for as low as $410. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the evening are often more expensive with an average ticket price of $535.

Cheap Oakland, California to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Caribbean

Best Price Found	$180
Fastest flight time	11h 05m
Direct flights	None
Airports in Caribbean	8 airports

The best one-way flight to Caribbean from Oakland, California in the past 72 hours is $180. The best round-trip flight deal from Oakland, California to Caribbean found on momondo in the last 72 hours is $365.

The fastest flight from Oakland, California to Caribbean takes 11h 05m

There are no direct flights from Oakland, California to Caribbean. Popular non-direct routes for this connection are Oakland Airport - San Juan Luis Munoz Marin Intl Airport, Oakland Airport - Punta Cana Airport and Oakland Airport - Santo Domingo Las Americas Airport.

There are 8 airports near Caribbean: Santo Domingo Las Americas (SDQ), Nassau Intl (NAS), Kingston Norman Manley (KIN), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), 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?
Prices for flights from Oakland Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Oakland Airport to Caribbean?
There are 2 operators available for flights from Oakland Airport to Caribbean as of August 2025.
How old do you have to be to fly from Oakland Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oakland Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Oakland, California to Caribbean

Compare and see reviews for airlines that fly from Oakland, California to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $260	Free Cancellation	Rating 6.3 8,040 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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Oakland to Caribbean for you.

Can I find flights from Oakland to Caribbean with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean from Oakland with this policy.

How can momondo help me find flights from Oakland to Caribbean?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oakland to Caribbean.

I’m not ready to book a flight from Oakland to Caribbean right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Oakland to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.