$219 Find Cheap Flights from Oakland to Caribbean - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Caribbean departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Oakland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$660
Santo Domingo
Santo Domingo2 stops$860
Montego Bay
Montego Bay2 stops$685
Oranjestad
Oranjestad2 stops$992
Nassau
Nassau2 stops$550
Saint Thomas Island
Saint Thomas Island2 stops$1,031
Kingston
Kingston2 stops$1,185
Simpson Bay
Simpson Bay2 stops$1,216
Bridgetown
Bridgetown2 stops$1,900
Willemstad
Willemstad3 stops$1,023
Punta Cana
Punta Cana2 stops$660
Santo Domingo
Santo Domingo2 stops$860
Montego Bay
Montego Bay2 stops$685
Oranjestad
Oranjestad2 stops$992
Nassau
Nassau2 stops$550
Saint Thomas Island
Saint Thomas Island2 stops$1,031
Kingston
Kingston2 stops$1,185
Simpson Bay
Simpson Bay2 stops$1,216
Bridgetown
Bridgetown2 stops$1,900
Willemstad
Willemstad3 stops$1,023

Book Cheap Oakland to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oakland to Caribbean

Tue, Aug 11 - Mon, Aug 31
Southwest Logo
7:45 pm - 11:00 am
OAK
-
SJU
12h 15m
2 stops
Southwest Logo
5:00 am - 3:00 pm
SJU
-
OAK
13h 00m
2 stops
$466Southwest
Wed, Aug 5 - Tue, Aug 11
Southwest Logo
6:15 am - 9:05 pm
OAK
-
SJU
11h 50m
2 stops
Southwest Logo
5:15 am - 1:55 pm
SJU
-
OAK
11h 40m
2 stops
$508Southwest
Wed, Aug 5 - Tue, Aug 11
Southwest Logo
6:15 am - 9:05 pm
OAK
-
SJU
11h 50m
2 stops
Southwest Logo
5:15 am - 1:55 pm
SJU
-
OAK
11h 40m
2 stops
$526Southwest
Thu, Jul 16 - Thu, Jul 30
Southwest Logo
6:20 am - 9:30 pm
OAK
-
SJU
12h 10m
2 stops
Southwest Logo
8:15 pm - 11:35 am
SJU
-
OAK
18h 20m
2 stops
$543Southwest
Mon, Sep 14 - Wed, Sep 16
Southwest Logo
8:25 pm - 12:15 pm
OAK
-
NAS
12h 50m
2 stops
Southwest Logo
1:10 pm - 11:55 pm
NAS
-
OAK
13h 45m
2 stops
$550Southwest
Sat, Nov 7 - Fri, Dec 11
Delta Logo
5:05 pm - 12:36 pm
OAK
-
SJU
15h 31m
2 stops
Delta Logo
1:55 pm - 11:56 pm
SJU
-
OAK
14h 01m
2 stops
$588Delta
Fri, Jul 24 - Thu, Jul 30
Southwest Logo
11:00 am - 1:25 am
OAK
-
SJU
11h 25m
2 stops
Southwest Logo
8:15 pm - 11:35 am
SJU
-
OAK
18h 20m
2 stops
$603Southwest
Wed, Nov 18 - Thu, Nov 26
Delta Logo
1:15 pm - 1:30 pm
OAK
-
NAS
21h 15m
2 stops
Delta Logo
2:55 pm - 11:56 pm
NAS
-
OAK
12h 01m
2 stops
$620Delta
Tue, Nov 17 - Wed, Nov 25
Delta Logo
5:55 am - 11:13 pm
OAK
-
SJU
13h 18m
2 stops
Delta Logo
1:55 pm - 11:56 pm
SJU
-
OAK
14h 01m
2 stops
$630Delta
Wed, Aug 5 - Wed, Aug 12
Multiple Airlines Logo
11:15 pm - 10:20 am
OAK
-
CUR
32h 05m
3 stops
Multiple Airlines Logo
6:15 pm - 9:44 pm
CUR
-
OAK
30h 29m
2 stops
$1,023Multiple 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.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oakland to Caribbean is August, when tickets cost $360 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $861 and $663 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$219
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Oakland to Nassau

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

 
Need help choosing which airline to fly with from Oakland to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4242 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Was fine, delayed and feels like southwest is always late

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Oakland (OAK)