What airlines fly to Caribbean?

American Airlines, United Airlines and JetBlue 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 48% 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?

Southwest and Delta 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 October 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.

$442 Cheap Flights from Oakland to Caribbean in 2025/26

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Find the cheapest flights from Oakland, California to Caribbean

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One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:25 am - 7:25 pmOAK-SJU

11h 00m2 stops

8:55 am - 6:10 pmSJU-OAK

13h 15m2 stops

$495Southwest

Find Deal

jue., oct. 30 - lun., nov. 3

5:55 am - 12:44 pmOAK-PUJ

27h 49m2 stops

3:56 pm - 11:50 amPUJ-OAK

22h 54m2 stops

$498Delta

Find Deal

sáb., oct. 25 - vie., oct. 31

5:00 am - 7:25 pmOAK-SJU

11h 25m2 stops

10:40 am - 9:25 pmSJU-OAK

13h 45m2 stops

$499Southwest

Find Deal

vie., oct. 24 - sáb., nov. 1

1:15 pm - 2:00 pmOAK-PUJ

20h 45m2 stops

5:18 pm - 10:53 pmPUJ-OAK

33h 35m2 stops

$500Delta

Find Deal

mar., ene. 6 - lun., ene. 12

1:15 pm - 11:10 amOAK-MBJ

18h 55m2 stops

12:35 pm - 11:53 pmMBJ-OAK

14h 18m2 stops

$504Delta

Find Deal

jue., ene. 29 - mar., feb. 3

5:25 am - 10:20 pmOAK-SJU

12h 55m2 stops

8:20 am - 5:20 pmSJU-OAK

13h 00m2 stops

$546Southwest

Find Deal

vie., nov. 14 - sáb., nov. 15

2:49 pm - 3:06 pmOAK-SJU

20h 17m2 stops

7:15 am - 10:25 amSJU-OAK

31h 10m2 stops

$776Alaska Airlines

Find Deal

sáb., nov. 15 - mié., nov. 19

2:49 pm - 2:08 pmOAK-SJU

20h 19m2 stops

4:30 pm - 11:59 pmSJU-OAK

34h 29m2 stops

$795Alaska Airlines

Find Deal

lun., oct. 27 - vie., oct. 31

12:30 pm - 5:02 pmOAK-PUJ

25h 32m3 stops

5:15 am - 6:57 pmPUJ-OAK

17h 42m2 stops

$973Multiple Airlines

Find Deal

vie., oct. 31 - dom., nov. 2

11:55 pm - 1:20 pmOAK-PUJ

34h 25m3 stops

5:15 am - 6:57 pmPUJ-OAK

17h 42m2 stops

$1,083Multiple Airlines

Find Deal

jue., oct. 30 - dom., nov. 2

Delta flights from Oakland, California to Caribbean

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

Delta

Oct 25

OAK5:55 amOakland

27h 49m

2 stops

PUJ12:44 pmPunta Cana

Oct 31

PUJ3:56 pmPunta Cana

22h 54m

2 stops

OAK11:50 amOakland

$498

Find similar

Delta

Jan 6

OAK1:15 pmOakland

20h 45m

2 stops

PUJ2:00 pmPunta Cana

Jan 12

PUJ5:18 pmPunta Cana

33h 35m

2 stops

OAK10:53 pmOakland

$500

Find similar

Delta

Jan 29

OAK1:15 pmOakland

18h 55m

2 stops

MBJ11:10 amMontego Bay Sangster Intl

Feb 3

MBJ12:35 pmMontego Bay Sangster Intl

14h 18m

2 stops

OAK11:53 pmOakland

$504

Find similar

Southwest flights from Oakland, California to Caribbean

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

Southwest

Oct 30

OAK5:25 amOakland

11h 00m

2 stops

SJU7:25 pmSan Juan Luis Munoz Marin Intl

Nov 3

SJU8:55 amSan Juan Luis Munoz Marin Intl

13h 15m

2 stops

OAK6:10 pmOakland

$495

Find similar

Southwest

Oct 24

OAK5:00 amOakland

11h 25m

2 stops

SJU7:25 pmSan Juan Luis Munoz Marin Intl

Nov 1

SJU10:40 amSan Juan Luis Munoz Marin Intl

13h 45m

2 stops

OAK9:25 pmOakland

$499

Find similar

Southwest

Nov 14

OAK5:25 amOakland

12h 55m

2 stops

SJU10:20 pmSan Juan Luis Munoz Marin Intl

Nov 15

SJU8:20 amSan Juan Luis Munoz Marin Intl

13h 00m

2 stops

OAK5:20 pmOakland

$546

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

jue. 10/30

5:25 am-7:25 pm

2 stops11h 00m

San Juan Luis Munoz Marin Intl

lun. 11/3

8:55 am-6:10 pm

2 stops13h 15m

$495

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

sáb. 10/25

5:55 am-12:44 pm

2 stops27h 49m

Punta Cana

vie. 10/31

3:56 pm-11:50 am

2 stops22h 54m

$498

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

vie. 10/24

5:00 am-7:25 pm

2 stops11h 25m

San Juan Luis Munoz Marin Intl

sáb. 11/1

10:40 am-9:25 pm

2 stops13h 45m

$499

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

mar. 1/6

1:15 pm-2:00 pm

2 stops20h 45m

Punta Cana

lun. 1/12

5:18 pm-10:53 pm

2 stops33h 35m

$500

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

jue. 1/29

1:15 pm-11:10 am

2 stops18h 55m

Montego Bay Sangster Intl

mar. 2/3

12:35 pm-11:53 pm

2 stops14h 18m

$504

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

vie. 11/14

5:25 am-10:20 pm

2 stops12h 55m

San Juan Luis Munoz Marin Intl

sáb. 11/15

8:20 am-5:20 pm

2 stops13h 00m

$546

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

sáb. 11/15

2:49 pm-3:06 pm

2 stops20h 17m

San Juan Luis Munoz Marin Intl

mié. 11/19

7:15 am-10:25 am

2 stops31h 10m

$776

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

lun. 10/27

2:49 pm-2:08 pm

2 stops20h 19m

San Juan Luis Munoz Marin Intl

vie. 10/31

4:30 pm-11:59 pm

2 stops34h 29m

$795

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

vie. 10/31

12:30 pm-5:02 pm

3 stops25h 32m

Punta Cana

dom. 11/2

5:15 am-6:57 pm

2 stops17h 42m

$973

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

jue. 10/30

11:55 pm-1:20 pm

3 stops34h 25m

Punta Cana

dom. 11/2

5:15 am-6:57 pm

2 stops17h 42m

$1,083

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 $358. If you don’t want to visit Caribbean in October, then you should wait until February to fly from Oakland, California, when ticket prices are also cheap, with an average price of $389.

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

Direct flights	None

There are no direct flights from Oakland, California to Caribbean. There are no popular flight routes from Oakland, California to Caribbean.

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 October 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 $278	Free Cancellation	Rating 6.3 8,077 reviews		Search Spirit Airlines flights
Southwest	PriceFrom $389	Free Cancellation	Rating 8.0 4,232 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.