$208 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 6/24. 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 Cana1 stop$601
Santo Domingo
Santo Domingo3 stops$793
Montego Bay
Montego Bay2 stops$706
Oranjestad
Oranjestad2 stops$686
Nassau
Nassau2 stops$458
Saint Thomas Island
Saint Thomas Island2 stops$757
Kingston
Kingston3 stops$1,297
Simpson Bay
Simpson Bay3 stops$1,161
Port of Spain
Port of Spain3 stops$1,502
Bridgetown
Bridgetown2 stops$3,517
Willemstad
Willemstad3 stops$1,458
Punta Cana
Punta Cana1 stop$601
Santo Domingo
Santo Domingo3 stops$793
Montego Bay
Montego Bay2 stops$706
Oranjestad
Oranjestad2 stops$686
Nassau
Nassau2 stops$458
Saint Thomas Island
Saint Thomas Island2 stops$757
Kingston
Kingston3 stops$1,297
Simpson Bay
Simpson Bay3 stops$1,161
Port of Spain
Port of Spain3 stops$1,502
Bridgetown
Bridgetown2 stops$3,517
Willemstad
Willemstad3 stops$1,458

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

Sun, May 10 - Wed, May 13
Southwest Logo
7:35 pm - 9:10 am
OAK
-
SJU
10h 35m
2 stops
Southwest Logo
8:10 am - 7:05 pm
SJU
-
OAK
13h 55m
2 stops
$366Southwest
Mon, Jul 6 - Tue, Jul 7
Southwest Logo
7:50 am - 12:25 am
OAK
-
SJU
13h 35m
2 stops
Southwest Logo
6:30 am - 1:50 pm
SJU
-
OAK
10h 20m
1 stop
$376Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
9:05 pm - 10:35 am
OAK
-
SJU
10h 30m
2 stops
Southwest Logo
8:10 am - 7:05 pm
SJU
-
OAK
13h 55m
2 stops
$381Southwest
Mon, Jul 6 - Tue, Jul 7
Southwest Logo
7:50 am - 12:25 am
OAK
-
SJU
13h 35m
2 stops
Southwest Logo
6:30 am - 4:00 pm
SJU
-
OAK
12h 30m
2 stops
$401Southwest
Sat, May 2 - Wed, May 6
Southwest Logo
7:35 pm - 9:05 am
OAK
-
SJU
10h 30m
2 stops
Southwest Logo
8:10 am - 7:05 pm
SJU
-
OAK
13h 55m
2 stops
$421Southwest
Tue, Apr 14 - Fri, Apr 24
Southwest Logo
9:05 pm - 10:35 am
OAK
-
SJU
10h 30m
2 stops
Southwest Logo
5:05 am - 3:05 pm
SJU
-
OAK
13h 00m
2 stops
$431Southwest
Tue, Mar 3 - Tue, Mar 10
Delta Logo
4:59 pm - 11:50 am
OAK
-
NAS
15h 51m
2 stops
Delta Logo
1:15 pm - 11:46 pm
NAS
-
OAK
13h 31m
2 stops
$458Delta
Thu, Mar 5 - Thu, Mar 12
Delta Logo
12:40 pm - 12:26 pm
OAK
-
NAS
20h 46m
2 stops
Delta Logo
6:10 pm - 11:51 am
NAS
-
OAK
20h 41m
2 stops
$532Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
5:55 am - 12:26 pm
OAK
-
NAS
27h 31m
2 stops
Delta Logo
6:10 pm - 4:00 pm
NAS
-
OAK
24h 50m
2 stops
$596Delta
Thu, May 7 - Sun, May 10
Multiple Airlines Logo
12:30 pm - 9:55 pm
OAK
-
PUJ
30h 25m
3 stops
Multiple Airlines Logo
6:15 am - 7:57 pm
PUJ
-
OAK
16h 42m
2 stops
$734Multiple 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 June, when the average cost of round-trip tickets is $925 and $653 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$208
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 6% 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 4282 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

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

2.0 MediocreDavid, Feb 2026
SAN - LAS
Read more Southwest reviews

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

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Oakland (OAK)