How does KAYAK find such low prices on flights from Oakland to Caribbean?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oakland to Caribbean. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Caribbean?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Oakland to Caribbean?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Oakland to Caribbean with an airline and back with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oakland to Caribbean?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Oakland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

Which airlines provide the cheapest flights from Oakland to Caribbean?

In the past 3 days, the cheapest round-trip tickets from Oakland to Caribbean were found on Southwest ($446) and Delta ($622).

Which airlines provide the cheapest flights from Oakland to Caribbean?

In the past 3 days, the cheapest round-trip tickets from Oakland to Caribbean were found on Southwest ($446) and Delta ($622).

How long does a flight from Oakland to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Oakland are to San Juan , which takes 10h 05m , Kingston , which takes 12h 00m, and Montego Bay , which takes 12h 40m.

How long does a flight from Oakland to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Oakland are to San Juan , which takes 10h 05m , Kingston , which takes 12h 00m, and Montego Bay , which takes 12h 40m.

$229 CHEAP FLIGHTS from Oakland to Caribbean

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Flight Deals

One-wayRound-trip

Punta Cana2 stops$689

Santo Domingo2 stops$2,861

Montego Bay2 stops$687

Oranjestad2 stops$671

Santiago de los Caballeros2 stops$1,436

Nassau2 stops$606

Saint Thomas Island2 stops$1,000

Kingston3 stops$923

Simpson Bay2 stops$664

Bridgetown2 stops$2,223

Willemstad3 stops$1,185

St. John's2 stops$1,246

Punta Cana2 stops$689

Santo Domingo2 stops$2,861

Montego Bay2 stops$687

Oranjestad2 stops$671

Santiago de los Caballeros2 stops$1,436

Nassau2 stops$606

Saint Thomas Island2 stops$1,000

Kingston3 stops$923

Simpson Bay2 stops$664

Bridgetown2 stops$2,223

Willemstad3 stops$1,185

St. John's2 stops$1,246

Book Cheap Oakland to Caribbean Plane Tickets

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Oakland to Caribbean

Sun, Aug 30 - Wed, Sep 16

7:40 pm - 10:55 am

OAK

SJU

12h 15m

2 stops

10:30 am - 8:00 pm

SJU

OAK

12h 30m

2 stops

$446Southwest

Sun, Aug 30 - Wed, Sep 16

7:40 pm - 10:55 am

OAK

SJU

12h 15m

2 stops

5:15 am - 1:55 pm

SJU

OAK

11h 40m

2 stops

$458Southwest

Sun, Aug 9 - Sat, Aug 15

7:40 pm - 9:10 am

OAK

SJU

10h 30m

2 stops

5:05 am - 1:40 pm

SJU

OAK

11h 35m

2 stops

$470Southwest

Thu, Oct 15 - Tue, Oct 27

6:15 am - 8:55 pm

OAK

SJU

11h 40m

2 stops

6:45 am - 5:05 pm

SJU

OAK

13h 20m

2 stops

$489Southwest

Tue, Jul 28 - Wed, Aug 5

10:25 am - 12:15 am

OAK

SJU

10h 50m

2 stops

5:15 am - 1:55 pm

SJU

OAK

11h 40m

2 stops

$567Southwest

Sun, Oct 18 - Sun, Oct 25

8:05 am - 11:35 pm

OAK

SJU

12h 30m

2 stops

5:30 am - 2:50 pm

SJU

OAK

12h 20m

2 stops

$569Southwest

Mon, Jul 6 - Tue, Jul 14

6:00 am - 11:51 am

OAK

NAS

26h 51m

2 stops

1:16 pm - 11:50 pm

NAS

OAK

13h 34m

2 stops

$611Delta

Mon, Aug 17 - Tue, Aug 25

4:57 pm - 11:51 am

OAK

NAS

15h 54m

2 stops

1:09 pm - 11:51 pm

NAS

OAK

13h 42m

2 stops

$622Delta

Sun, Aug 30 - Wed, Sep 16

4:57 pm - 11:56 am

OAK

SJU

15h 59m

2 stops

7:30 am - 11:49 pm

SJU

OAK

19h 19m

2 stops

$630Delta

Sat, Jun 20 - Sat, Jun 27

8:22 pm - 6:38 pm

OAK

PUJ

19h 16m

2 stops

9:18 am - 9:44 pm

PUJ

OAK

15h 26m

2 stops

$699Multiple Airlines

Booking Insights

KAYAK's insights & trends for Oakland to Caribbean flights

Get data-powered insights and trends into flights from Oakland to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Prices

Airlines

The cheapest month for flights from Oakland to Caribbean is May, when tickets cost $287 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $663 and $495 respectively.

Find deals

Low season	October
High season	July
Cheapest flight	$229

Best time to beat the crowds with an average 37% drop in price.

Most popular time to fly and prices are also 13% lower on average.

Flight from Oakland to San Juan

How does KAYAK find such low prices on flights from Oakland to Caribbean?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oakland to Caribbean.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Caribbean?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Oakland to Caribbean?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Oakland to Caribbean with an airline and back with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oakland to Caribbean?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Oakland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

8.0

SouthwestOverall score based on 4295 reviews

8.6Crew

8.1Boarding

7.5Entertainment

7.0Food

8.0Comfort

Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026

LGB - PHX

Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Everything you need to know for your flight to Caribbean

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Information on your arrival and departure airports

Oakland (OAK)

$229 Find Cheap Flights from Oakland to Caribbean

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Cheap Flights from Oakland to Caribbean

Book Cheap Oakland to Caribbean Plane Tickets

Recent round-trip flight deals from Oakland to Caribbean

Recent one-way flight deals from Oakland to Caribbean

Recent last minute flight deals from Oakland to Caribbean

KAYAK's insights & trends for Oakland to Caribbean flights

Get data-powered insights and trends into flights from Oakland to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Oakland to Caribbean?

The cheapest month for flights from Oakland to Caribbean is May, when tickets cost $287 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $663 and $495 respectively.

Which airlines provide the cheapest flights from Oakland to Caribbean?

In the past 3 days, the cheapest round-trip tickets from Oakland to Caribbean were found on Southwest ($446) and Delta ($622).

How long does a flight from Oakland to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Oakland are to San Juan, which takes 10h 05m, Kingston, which takes 12h 00m, and Montego Bay, which takes 12h 40m.

Good to know

FAQs - booking Caribbean flights

How does KAYAK find such low prices on flights from Oakland to Caribbean?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oakland to Caribbean.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Caribbean?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Oakland to Caribbean?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Oakland to Caribbean with an airline and back with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oakland to Caribbean?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Oakland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Oakland to Caribbean

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Cabin class types available on flights to Oakland

Complete your trip to Caribbean with a hotel stay or car rental

Flights to other popular destinations

Flights from domestic origins to Oakland

Flights to popular destinations in Caribbean

Find deals for your return flight