$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 2/16. 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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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$690
Santo Domingo
Santo Domingo2 stops$782
Montego Bay
Montego Bay2 stops$570
Oranjestad
Oranjestad2 stops$896
Nassau
Nassau2 stops$592
Saint Thomas Island
Saint Thomas Island2 stops$1,103
Kingston
Kingston2 stops$928
Simpson Bay
Simpson Bay2 stops$856
Bridgetown
Bridgetown2 stops$1,103
Willemstad
Willemstad2 stops$1,511
St. John's
St. John's2 stops$1,343
Punta Cana
Punta Cana2 stops$690
Santo Domingo
Santo Domingo2 stops$782
Montego Bay
Montego Bay2 stops$570
Oranjestad
Oranjestad2 stops$896
Nassau
Nassau2 stops$592
Saint Thomas Island
Saint Thomas Island2 stops$1,103
Kingston
Kingston2 stops$928
Simpson Bay
Simpson Bay2 stops$856
Bridgetown
Bridgetown2 stops$1,103
Willemstad
Willemstad2 stops$1,511
St. John's
St. John's2 stops$1,343

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

Mon, Feb 23 - Fri, Feb 27
Southwest Logo
8:30 am - 12:40 amOAK-SJU
12h 10m2 stops
Southwest Logo
7:00 am - 3:00 pmSJU-OAK
12h 00m2 stops
$385Southwest
Find Deal
Sun, Dec 7 - Wed, Dec 17
Southwest Logo
7:45 pm - 10:25 amOAK-SJU
10h 40m2 stops
Southwest Logo
5:45 am - 2:05 pmSJU-OAK
12h 20m2 stops
$444Southwest
Find Deal
Wed, Dec 3 - Sat, Dec 13
Southwest Logo
9:00 am - 12:35 amOAK-SJU
11h 35m2 stops
Southwest Logo
5:40 am - 2:25 pmSJU-OAK
12h 45m2 stops
$489Southwest
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
7:10 pm - 11:35 amOAK-SJU
12h 25m2 stops
Southwest Logo
5:45 am - 2:05 pmSJU-OAK
12h 20m2 stops
$509Southwest
Find Deal
Mon, Dec 15 - Fri, Dec 19
Southwest Logo
7:10 pm - 10:25 amOAK-SJU
11h 15m2 stops
Southwest Logo
7:30 am - 5:35 pmSJU-OAK
14h 05m2 stops
$521Southwest
Find Deal
Fri, Feb 27 - Sat, Mar 7
Southwest Logo
7:50 pm - 10:00 amOAK-SJU
10h 10m2 stops
Southwest Logo
3:35 pm - 12:20 amSJU-OAK
12h 45m1 stop
$531Southwest
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Wed, Dec 17 - Wed, Dec 24
Delta Logo
5:55 am - 11:09 amOAK-MBJ
26h 14m2 stops
Delta Logo
2:23 pm - 11:54 amMBJ-OAK
24h 31m2 stops
$570Delta
Find Deal
Wed, Dec 31 - Wed, Jan 7
Delta Logo
12:34 pm - 12:20 pmOAK-NAS
20h 46m2 stops
Delta Logo
1:41 pm - 10:53 pmNAS-OAK
12h 12m2 stops
$592Delta
Find Deal
Tue, Dec 16 - Thu, Dec 25
Delta Logo
4:50 pm - 1:30 pmOAK-NAS
17h 40m2 stops
Delta Logo
1:31 pm - 10:47 pmNAS-OAK
12h 16m2 stops
$619Delta
Find Deal
Tue, Jan 13 - Mon, Jan 19
Multiple Airlines Logo
7:33 pm - 12:54 amOAK-PUJ
25h 21m2 stops
Multiple Airlines Logo
10:35 pm - 10:19 pmPUJ-OAK
27h 44m3 stops
$842Multiple Airlines
Find Deal
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 January, when the average cost of round-trip tickets is $873 and $695 respectively.

Good to know

Low seasonOctober
Cheapest flight$208
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 4% increase in price.
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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $410 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $535.

Reviews of the top airlines 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 4245 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

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

10.0 ExcellentGordon, Nov 2025SAN - OAK
Read more Southwest reviews

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.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

No leg room. My knee was sore for a day.

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Flight was cancelled without warning close to flight date. Stuck witha credit has to buy a new ticket from another airline in either to get to location. Email cancelling was lost in mail.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

Unbelievable check in horrible. Asked to print tickets at the gate after a delay

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports