$247 Find Cheap Flights from Oakland to Caribbean

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 7/22. 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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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$561
Montego Bay
Montego Bay2 stops$593
Oranjestad
Oranjestad2 stops$726
Nassau
Nassau2 stops$509
Saint Thomas Island
Saint Thomas Island2 stops$563
Kingston
Kingston2 stops$1,243
Willemstad
Willemstad2 stops$2,662
Punta Cana
Punta Cana2 stops$561
Montego Bay
Montego Bay2 stops$593
Oranjestad
Oranjestad2 stops$726
Nassau
Nassau2 stops$509
Saint Thomas Island
Saint Thomas Island2 stops$563
Kingston
Kingston2 stops$1,243
Willemstad
Willemstad2 stops$2,662

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

Fri, May 8 - Wed, May 13
Delta Logo
5:05 pm - 12:01 pm
OAK
-
SJU
15h 56m
2 stops
Delta Logo
2:35 pm - 11:57 pm
SJU
-
OAK
12h 22m
2 stops
$426Delta
Fri, May 8 - Wed, May 13
Delta Logo
5:05 pm - 12:01 pm
OAK
-
SJU
15h 56m
2 stops
Delta Logo
2:35 pm - 11:57 pm
SJU
-
OAK
12h 22m
2 stops
$461Delta
Fri, Apr 24 - Fri, May 1
Southwest Logo
11:55 pm - 1:20 pm
OAK
-
SJU
10h 25m
1 stop
Southwest Logo
6:50 am - 6:20 pm
SJU
-
OAK
14h 30m
2 stops
$494Southwest
Sat, Apr 18 - Wed, Apr 22
Delta Logo
5:55 am - 11:12 pm
OAK
-
SJU
14h 17m
2 stops
Delta Logo
12:55 pm - 11:54 pm
SJU
-
OAK
13h 59m
2 stops
$508Delta
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
9:20 pm - 1:15 pm
OAK
-
NAS
12h 55m
2 stops
Southwest Logo
2:10 pm - 11:25 pm
NAS
-
OAK
12h 15m
2 stops
$509Southwest
Sat, May 2 - Tue, May 5
Southwest Logo
6:10 am - 9:25 pm
OAK
-
SJU
12h 15m
2 stops
Southwest Logo
8:10 am - 6:50 pm
SJU
-
OAK
13h 40m
2 stops
$530Southwest
Fri, May 8 - Fri, May 15
Southwest Logo
8:30 pm - 1:00 pm
OAK
-
PUJ
13h 30m
2 stops
Southwest Logo
4:00 pm - 10:00 am
PUJ
-
OAK
21h 00m
2 stops
$561Southwest
Mon, Jul 13 - Mon, Jul 20
Southwest Logo
7:40 pm - 1:45 pm
OAK
-
STT
15h 05m
2 stops
Southwest Logo
2:45 pm - 11:45 pm
STT
-
OAK
12h 00m
2 stops
$563Southwest
Sun, May 31 - Thu, Jun 4
Southwest Logo
6:05 am - 12:05 am
OAK
-
SJU
15h 00m
2 stops
Southwest Logo
10:20 pm - 11:35 am
SJU
-
OAK
16h 15m
2 stops
$566Southwest
Tue, Apr 14 - Sun, Apr 19
Multiple Airlines Logo
1:22 pm - 3:50 pm
OAK
-
AUA
23h 28m
3 stops
Multiple Airlines Logo
5:20 pm - 9:44 pm
AUA
-
OAK
31h 24m
3 stops
$997Multiple 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 October, when tickets cost $382 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $925 and $666 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$247
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Oakland to San Juan

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.
8.0
SouthwestOverall score based on 4333 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

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

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

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

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

Great flight but super high price. Glad it was a business trip and not personal

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Oakland (OAK)