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 38% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 12 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 Alaska Airlines 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 March 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.

$247 Cheap Flights from Oakland to Caribbean Islands in 2026

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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.

5:05 pm - 12:01 pm

OAK

SJU

15h 56m

2 stops

2:35 pm - 11:57 pm

SJU

OAK

12h 22m

2 stops

$426Delta

Fri, May 8 - Wed, May 13

5:05 pm - 12:01 pm

OAK

SJU

15h 56m

2 stops

2:35 pm - 11:57 pm

SJU

OAK

12h 22m

2 stops

$461Delta

Fri, May 8 - Wed, May 13

11:55 pm - 1:20 pm

OAK

SJU

10h 25m

1 stop

6:50 am - 6:20 pm

SJU

OAK

14h 30m

2 stops

$494Southwest

Fri, Apr 24 - Fri, May 1

5:55 am - 11:12 pm

OAK

SJU

14h 17m

2 stops

12:55 pm - 11:54 pm

SJU

OAK

13h 59m

2 stops

$508Delta

Sat, Apr 18 - Wed, Apr 22

9:20 pm - 1:15 pm

OAK

NAS

12h 55m

2 stops

2:10 pm - 11:25 pm

NAS

OAK

12h 15m

2 stops

$509Southwest

Wed, Apr 22 - Wed, Apr 29

6:10 am - 9:25 pm

OAK

SJU

12h 15m

2 stops

8:10 am - 6:50 pm

SJU

OAK

13h 40m

2 stops

$530Southwest

Sat, May 2 - Tue, May 5

8:30 pm - 1:00 pm

OAK

PUJ

13h 30m

2 stops

4:00 pm - 10:00 am

PUJ

OAK

21h 00m

2 stops

$561Southwest

Fri, May 8 - Fri, May 15

7:40 pm - 1:45 pm

OAK

STT

15h 05m

2 stops

2:45 pm - 11:45 pm

STT

OAK

12h 00m

2 stops

$563Southwest

Mon, Jul 13 - Mon, Jul 20

5:55 am - 11:35 am

OAK

PUJ

26h 40m

2 stops

5:05 pm - 11:53 am

PUJ

OAK

21h 48m

2 stops

$659Delta

Fri, Apr 17 - Sat, Apr 25

1:22 pm - 3:50 pm

OAK

AUA

23h 28m

3 stops

5:20 pm - 9:44 pm

AUA

OAK

31h 24m

3 stops

$997Multiple Airlines

Tue, Apr 14 - Sun, Apr 19

Delta flights from Oakland, California to Caribbean Islands

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

Delta

May 8

OAK5:05 pmOakland

15h 56m

2 stops

SJU12:01 pmSan Juan Luis Munoz Marin Intl

May 13

SJU2:35 pmSan Juan Luis Munoz Marin Intl

12h 22m

2 stops

OAK11:57 pmOakland

$426

Delta

May 8

OAK5:05 pmOakland

15h 56m

2 stops

SJU12:01 pmSan Juan Luis Munoz Marin Intl

May 13

SJU2:35 pmSan Juan Luis Munoz Marin Intl

12h 22m

2 stops

OAK11:57 pmOakland

$461

Delta

Apr 18

OAK5:55 amOakland

14h 17m

2 stops

SJU11:12 pmSan Juan Luis Munoz Marin Intl

Apr 22

SJU12:55 pmSan Juan Luis Munoz Marin Intl

13h 59m

2 stops

OAK11:54 pmOakland

$508

Alaska Airlines flights from Oakland, California to Caribbean Islands

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

Alaska Airlines

Jun 2

OAK8:15 pmOakland

24h 24m

2 stops

SJU11:39 pmSan Juan Luis Munoz Marin Intl

Jun 5

SJU12:44 amSan Juan Luis Munoz Marin Intl

20h 37m

2 stops

OAK6:21 pmOakland

$691

Alaska Airlines

May 4

OAK6:41 amOakland

13h 21m

2 stops

SJU11:02 pmSan Juan Luis Munoz Marin Intl

May 7

SJU11:59 pmSan Juan Luis Munoz Marin Intl

25h 24m

2 stops

OAK10:23 pmOakland

$749

Alaska Airlines

Jun 2

OAK8:15 pmOakland

24h 24m

2 stops

SJU11:39 pmSan Juan Luis Munoz Marin Intl

Jun 10

SJU5:30 amSan Juan Luis Munoz Marin Intl

20h 07m

2 stops

OAK10:37 pmOakland

$766

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

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/8

5:05 pm-12:01 pm

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Wed 5/13

2:35 pm-11:57 pm

2 stops12h 22m

$426

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/8

5:05 pm-12:01 pm

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Wed 5/13

2:35 pm-11:57 pm

2 stops12h 22m

$461

Quickest round-trip

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 4/24

11:55 pm-1:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Fri 5/1

6:50 am-6:20 pm

2 stops14h 30m

$494

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 4/18

5:55 am-11:12 pm

2 stops14h 17m

San Juan Luis Munoz Marin Intl

Wed 4/22

12:55 pm-11:54 pm

2 stops13h 59m

$508

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Wed 4/22

9:20 pm-1:15 pm

2 stops12h 55m

Nassau Intl

Wed 4/29

2:10 pm-11:25 pm

2 stops12h 15m

$509

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 5/2

6:10 am-9:25 pm

2 stops12h 15m

San Juan Luis Munoz Marin Intl

Tue 5/5

8:10 am-6:50 pm

2 stops13h 40m

$530

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 5/8

8:30 pm-1:00 pm

2 stops13h 30m

Punta Cana

Fri 5/15

4:00 pm-10:00 am

2 stops21h 00m

$561

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Mon 7/13

7:40 pm-1:45 pm

2 stops15h 05m

Saint Thomas Island Cyril E King

Mon 7/20

2:45 pm-11:45 pm

2 stops12h 00m

$563

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 4/17

5:55 am-11:35 am

2 stops26h 40m

Punta Cana

Sat 4/25

5:05 pm-11:53 am

2 stops21h 48m

$659

OaklandOranjestad

OAK - AUA

OAKAUA

Oakland

Tue 4/14

1:22 pm-3:50 pm

3 stops23h 28m

Oranjestad Reina Beatrix

Sun 4/19

5:20 pm-9:44 pm

3 stops31h 24m

$997

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 $382. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Oakland, California averaging around $500.

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 25m
Direct flights	None

The fastest flight from Oakland, California to Caribbean Islands takes 10h 25m

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 is 1 operator available for flights from Oakland Airport to Caribbean Islands as of March 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 26.22% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 15.86%, Airbus A320neo with 10.34%, and Airbus A320-100/200 with 8.45%.

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 $410	Free Cancellation	Rating 8.0 4,333 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.