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Find cheap flights from Oakland to Caribbean from $164

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 9/23. 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
0 bags
Thu 6/27
Thu 7/4

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana2 stops$489
Montego Bay
Montego Bay3 stops$561
Santo Domingo
Santo Domingo2 stops$514
Oranjestad
Oranjestad1 stop$583
Nassau
Nassau1 stop$623
Kingston
Kingston2 stops$629
Simpson Bay
Simpson Bay1 stop$2,149
Providenciales
Providenciales1 stop$587
Bridgetown
Bridgetown3 stops$846

Good to know

Low season

January

High season

June

Cheapest flight

$164
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 5% 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 to Caribbean from Oakland 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 to Caribbean with an airline and back to Oakland 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 to Caribbean from Oakland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 101% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving 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
DeltaOverall score based on 10502 reviews
7.4Food
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

There was a loud squeaky sound the whole time we were flying.

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Honestly, I didn’t expect that I will experience this long time wait during the check in. There was only one person who was taking care of the passengers for the economy class and it took us to wait about one hour to do our check i. As a result we barely get to the airplane as the gate was at the end of the airport. That is totally not professional where one crue is working at the registration desk with economy and 3-4 crues are helping for the business class.

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

They stuck us with multiple extra fees. I will never fly spirit again

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

Kayak does not know that spirit airlines charged me $70 to fly. But the bag check-in was $89 each way. This is false advertising to lure people. Spirit airlines sends bunch of emails after flight purchases to buy wifi, better seats, priority boarding, secure reserved seats. This is false advertising. Up front pricing. I would of flown jet blue or Alaska airlines.

One hour late taking off. Concerning, very hard landing. Uncomfortable seats with no recline. Extremely slow baggage claim. Very professional, knowledgeable flight attendants. Brand new, very clean plane.

Can’t say there was anything I particularly liked. Seats were very tight, leather wrapped plastic. I followed up a much longer and cheaper trip from Honolulu on southwest, everything was phenomenal, this flight was the exact opposite. Blows my mind they charge for water of all things. One of the attendants seemed very rude, I watched a taller gentleman a couple rows forward with his knees pressed into the back of the seat ahead, while the woman in that seat leaned forward the entire flight, I’m sure because she could feel his knees. I’ll be avoiding spirit like the plague from here forward.

Didn’t make the connecting flight due to a delay on our first flight.

I felt scam to have to pay $50 additional for my carry on luggage which was free for my other airline.

Book cheap flights from Oakland to Caribbean

Recent round-trip flight deals

9/4Wed
2 stopsSpirit Airlines
11h 30mOAK-SJU
9/9Mon
2 stopsSpirit Airlines
16h 09mSJU-OAK
$315
9/5Thu
2 stopsSpirit Airlines
21h 16mOAK-SJU
9/11Wed
2 stopsSpirit Airlines
16h 32mSJU-OAK
$337
6/11Tue
2 stopsSpirit Airlines
25h 25mOAK-STT
6/18Tue
2 stopsSpirit Airlines
20h 38mSTT-OAK
$341
9/5Thu
2 stopsSpirit Airlines
21h 16mOAK-SJU
9/10Tue
2 stopsSpirit Airlines
21h 23mSJU-OAK
$344
8/18Sun
1 stopDelta
11h 27mOAK-SJU
8/23Fri
2 stopsDelta
11h 43mSJU-OAK
$424
8/19Mon
1 stopDelta
11h 27mOAK-SJU
8/24Sat
1 stopDelta
11h 45mSJU-OAK
$429
7/3Wed
2 stops
25h 25mOAK-STT
7/8Mon
3 stops
26h 52mSTT-OAK
$609
6/23Sun
2 stops
12h 30mOAK-NAS
6/30Sun
3 stops
19h 51mNAS-OAK
$715
6/10Mon
2 stopsAmerican Airlines
18h 50mOAK-PUJ
6/17Mon
2 stopsAmerican Airlines
15h 10mPUJ-OAK
$5,775
6/12Wed
2 stopsAmerican Airlines
18h 40mOAK-MBJ
6/18Tue
2 stopsAmerican Airlines
15h 20mMBJ-OAK
$5,798

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Recent one-way flight deals

9/23Mon
2 stopsSpirit Airlines
20h 26mOAK-SJU
$164
6/26Wed
3 stopsSpirit Airlines
26h 50mOAK-SJU
$166
6/10Mon
2 stopsSpirit Airlines
20h 16mOAK-SJU
$167
8/24Sat
2 stopsSpirit Airlines
11h 30mOAK-SJU
$175
6/18Tue
2 stopsSpirit Airlines
25h 25mOAK-STT
$181
6/26Wed
2 stopsSpirit Airlines
18h 28mOAK-SJU
$182
6/2Sun
3 stops
32h 33mOAK-SJU
$253
8/4Sun
1 stopDelta
11h 27mOAK-SJU
$257
8/2Fri
1 stopDelta
11h 27mOAK-SJU
$262
8/3Sat
1 stopDelta
11h 27mOAK-SJU
$306

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Last minute flights from Oakland to Caribbean

Last minute flight, train and bus deals

6/1Sat
multi-stopSpirit Airlines
18h 24mOAK-SJU
6/6Thu
multi-stopSpirit Airlines
28h 05mSJU-OAK
$745
5/31Fri
multi-stopDelta
15h 55mOAK-SDQ
6/5Wed
multi-stopDelta
20h 16mSDQ-OAK
$815
5/31Fri
multi-stopSpirit Airlines
25h 38mOAK-STT
6/2Sun
multi-stopSpirit Airlines
24h 21mSTT-OAK
$822
5/30Thu
multi-stopSpirit Airlines
17h 40mOAK-SJU
6/2Sun
multi-stopSpirit Airlines
22h 31mSJU-OAK
$830
5/31Fri
multi-stopSpirit Airlines
20h 59mOAK-SJU
6/2Sun
multi-stopSpirit Airlines
22h 31mSJU-OAK
$997
5/31Fri
multi-stopSpirit Airlines
20h 59mOAK-SJU
6/2Sun
multi-stopSpirit Airlines
21h 51mSJU-OAK
$1,003
6/2Sun
multi-stopSpirit Airlines
17h 46mOAK-SDQ
6/9Sun
multi-stopSpirit Airlines
21h 53mSDQ-OAK
$1,125

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