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Find cheap flights from Oakland to Caribbean Islands from $162

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 Islands departing on 5/20. 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 6/6
Thu 6/13

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cana2 stops$519
Montego Bay
Montego Bay2 stops$573
Santo Domingo
Santo Domingo2 stops$736
Nassau
Nassau3 stops$525
Kingston
Kingston1 stop$698
Simpson Bay
Simpson Bay2 stops$891
Providenciales
Providenciales1 stop$582
Willemstad
Willemstad2 stops$5,792

Good to know

Low season

September

High season

June

Cheapest flight

$162
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Oakland to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Oakland to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 3 airlines serving from Oakland to Caribbean Islands

 
Need help choosing which airline to fly with from Oakland to Caribbean Islands? 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 10818 reviews
8.6Crew
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

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

6.0 GoodEliza, Apr 2024SAN - LAX
Read more about Delta reviews

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).

You need to be a hacker to get the (Free) WiFi

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

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.

Enjoyed the experience, on time flights, friendly staff the WiFi was intros d kept cutting out.

Awful experience. Both flights were delayed several times with weather but also crew members being the official cause. The vouchers are unusable and insufficient ($50 voucher to fly the same crappy airline is a joke for putting me on a red-eye that landed at 3:00 am). The aircrafts were old and uncomfortable (have a real pocket on the seat, for crying out loud!).

Its so random that they only allow 40 pounds on checked bags when all airlines take 55. They then charge you for each 10 extra pounds, so my checked suitcase was $130 and the flight $30 ... its like whattt, im for sure not traveling with Spirit again

It wasn’t as horrible as I would have expected, however, to not provide water and change so much for bags is a ripoff to say the least.

Book cheap flights from Oakland to Caribbean Islands

Recent round-trip flight deals

6/1Sat
2 stopsSpirit Airlines
20h 24mOAK-SJU
6/5Wed
2 stopsSpirit Airlines
19h 49mSJU-OAK
$264
6/1Sat
2 stopsSpirit Airlines
20h 24mOAK-SJU
6/4Tue
2 stopsSpirit Airlines
21h 53mSJU-OAK
$266
6/1Sat
2 stopsSpirit Airlines
20h 24mOAK-SJU
6/4Tue
3 stopsSpirit Airlines
21h 53mSJU-OAK
$279
6/4Tue
2 stopsSpirit Airlines
18h 28mOAK-SJU
6/11Tue
2 stopsSpirit Airlines
13h 01mSJU-OAK
$287
5/26Sun
3 stops
18h 15mOAK-SJU
5/29Wed
2 stops
24h 28mSJU-OAK
$343
5/26Sun
2 stops
18h 20mOAK-SJU
5/29Wed
2 stops
24h 28mSJU-OAK
$346
10/6Sun
1 stopDelta
10h 02mOAK-SJU
10/10Thu
1 stopDelta
10h 10mSJU-OAK
$472
7/21Sun
1 stopDelta
10h 49mOAK-PLS
8/1Thu
1 stopDelta
10h 45mPLS-OAK
$582
5/24Fri
2 stopsAmerican Airlines
24h 00mOAK-CUR
5/29Wed
3 stopsAmerican Airlines
30h 28mCUR-OAK
$5,792
5/24Fri
2 stopsAmerican Airlines
19h 10mOAK-SJU
5/28Tue
2 stopsAmerican Airlines
26h 14mSJU-OAK
$5,796

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Recent one-way flight deals

5/20Mon
2 stopsSpirit Airlines
35h 17mOAK-SJU
$162
6/4Tue
3 stopsSpirit Airlines
26h 55mOAK-PUJ
$189
6/19Wed
2 stopsSpirit Airlines
18h 28mOAK-SJU
$193
6/5Wed
3 stopsSpirit Airlines
29h 14mOAK-PUJ
$195
6/5Wed
2 stopsSpirit Airlines
21h 14mOAK-PUJ
$196
7/5Fri
2 stops
12h 30mOAK-NAS
$227
7/5Fri
3 stops
20h 25mOAK-NAS
$281
6/22Sat
2 stopsDelta
20h 26mOAK-SJU
$311
7/5Fri
1 stopDelta
15h 07mOAK-NAS
$353
5/20Mon
3 stopsAmerican Airlines
19h 10mOAK-SJU
$1,207

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Last minute flights from Oakland to Caribbean Islands

Last minute flight, train and bus deals

5/9Thu
multi-stopSpirit Airlines
35h 52mOAK-SJU
5/13Mon
multi-stopSpirit Airlines
38h 13mSJU-OAK
$796
5/7Tue
multi-stopDelta
17h 15mOAK-SDQ
5/9Thu
multi-stopDelta
12h 21mSDQ-OAK
$855
5/9Thu
multi-stopSpirit Airlines
35h 52mOAK-SJU
5/13Mon
multi-stopSpirit Airlines
17h 05mSJU-OAK
$883
5/7Tue
multi-stopDelta
17h 15mOAK-SDQ
5/9Thu
multi-stopDelta
25h 26mSDQ-OAK
$895
5/10Fri
multi-stopSpirit Airlines
20h 59mOAK-SJU
5/12Sun
multi-stopSpirit Airlines
21h 51mSJU-OAK
$996
5/9Thu
multi-stopSpirit Airlines
35h 52mOAK-SJU
5/12Sun
multi-stopSpirit Airlines
24h 30mSJU-OAK
$1,020
5/9Thu
multi-stopAmerican Airlines
22h 35mOAK-SJU
5/13Mon
multi-stopAmerican Airlines
28h 21mSJU-OAK
$2,739
5/9Thu
multi-stopAmerican Airlines
22h 35mOAK-SJU
5/12Sun
multi-stopAmerican Airlines
21h 31mSJU-OAK
$2,781
5/9Thu
multi-stopAmerican Airlines
22h 35mOAK-SJU
5/13Mon
multi-stopAmerican Airlines
15h 03mSJU-OAK
$2,968

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Oakland - Caribbean Islands Flights

Departure:

Oakland (OAK)United States

Return flight deals:

Caribbean Islands - Oakland

Cabin classes:

$318
$297
$190
$51