Find cheap flights from Oakland to Caribbean

Find cheap flights from Oakland to Caribbean

Round-trip
Economy
Oakland (OAK)
Caribbean
Wed 11/25
Wed 12/2
Any month
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Good to know

Low season

July Best time to beat the crowds with an average 6% drop in price.

High season

November Most popular time to fly with an average 24% increase in price.

Average price round-trip

$627 (avg. price over the last 2 weeks)

Good deal round-trip

$358 or less

Good deal one-way

$164 or less

Top tips for finding cheap flights to Caribbean

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean is August.
  • Morning departure is around 146% 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

FAQs - booking Caribbean flights

How long is the flight to Caribbean from Oakland?

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How does KAYAK find such low prices on flights to Caribbean?

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Top airlines flying Oakland to Caribbean

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,783 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Definitely pick comfort plus on this flight if you can. You can walk around a lot more on this flight compared to other flights. Food was really good! Recommend the overnight flights...."
Cons: "More leg room would have been nice..."

Pros: "Flight attendants were excellent."
Cons: "Satisfied with flight. It was as expected."

Cons: "I think all was very good"

Cons: "Communicating take off time!!! It changed multiple times by one three hours and ended up flying the next day!"

Cons: "long delay in boarding"

Cons: "Flight was delayed"

Pros: "Yes crew was great"
Cons: "More leg space"

Pros: "Crew attentive and helpful"
Cons: "N/a"

Cons: "They sent my luggage to a completely different state! Now I have to wait till it gets to LGA and then they’ll send it to me."

Cons: "Let passengers know from JFK there is a shuttle or air tram to your actual gate of departure. This could help with what the passenger may have as carry on item"

Cons: "It was perfect."

Cons: "Everything was excellent."

Pros: "Great flight"

Cons: "Crew at the gate made us return to get our immigration forms without our boarding passes. This forced us to miss the connecting flight to detroit and delay our arrival by 7 hours. Awful experience."

Cons: "I checked two bags and paid for them. The flight was full. I dutifully got in line for zone two. Next thing you know, at least 25 people got to board early and have free bag check. Really? I should get $35 dollar refund."

Pros: "Delta was OK"
Cons: "Lack of attention by the fly stuard in Virgin Australia Virgin had a 45´delay"

Pros: "Nothing."
Cons: "I missed check in (not flight) by 5 minutes. Delta did nothing. I called Aeromexico. After 30 minutes on hold they told me there was nothing they could do. Called Kayak, you guys said you couldn’t do anything. Finally I got some 3rd party phone number I was given by Kayak. I called the number and it was not in service. In all my years using this app this was the biggest disappointment ever!!!!"

Pros: "Comfortable, but expensive flight from Seattle to Gdansk via Amsterdam. The airport is large with many shops to search for chocolate."
Cons: "The 3-hour layover was long. 2 would be nicer."

Pros: "Charging stations, roomy seats"
Cons: "One attendant was a bit snarky."

Pros: "Nothing"
Cons: "Flight was horrible"

Pros: "Staff"

Pros: "Very good flight. Nice staff that seemed to enjoy their jobs. Great smiles and personable. Modern and clean plane with WiFi and charging outlets"
Cons: "There was a mechanical issue that delayed departure. Fortunately I did not have a connection to make. The crew made sure to communicate with everyone onboard frequently so we were aware of the situation and progress. They handled everything well which was reassuring for my peace of mind."

Pros: "And arrived early, too.☺"

Pros: "It got me home, eventually."
Cons: "Poor communication, a 6 hour delay followed by a 7 hour layover (during which we had to sleep on an airport floor because Delta couldn't offer us any hotel vouchers). Gate agents disappeared after 7pm becuase they were due to be done with their shifts when our flight was originally supposed to leave at 6 pm. It felt like we were trapped in the movie The Terminal. Oh! And our bag was misrouted, because that was just how things went those 2 days. All in all a 6 hour trip turned into 18 hours. I could have driven home in that amount of time!"

Pros: "Customer service was great"

Pros: "Helpful DCA counter personnel, cabin crew and comfy aircraft. On time both ways!"

Pros: "Great service, free movies, nice crew."

Cons: "They change schedule day before we flight, the change schedule 2 time while were flighting"

Pros: "Could be among the best landings ever. I felt nothing as we touched down in Salt Lake!!!"

Cons: "Rude staff"

Pros: "We didn’t order food and there was no in flight tv/entertainment"

Cons: "The plane bathroom was old and junky"

Pros: "Two Delta agents a kiosk assistance were not aware of the Hurricane Irma policy of waiving baggage fees to my destination. I informed them that the website indicated it would waive baggage fees to certain destinations if checked in at the airport before a certain date. Another Delta agent nearby had to show them a copy of the policy before I could get my baggage fees waived."

Cons: "There is just not enough leg room for a flight that long and the seats don't recline enough to be comfortable unless you upgrade and the tickets were already overpriced."

Pros: "NOTHING AT ALL!!!!"
Cons: "everything 1st of all i didnt like the fact that the stuff could act so unprofessional and very disrespectful and not knowing what type of info to give that made me lose my flight and at the end they all told me they couldnt help me to get my flight or anything not even try.."

Pros: "Good Snacks, crew is friendly, toilet was clean and we arrived on time"
Cons: "Nothing"

Cons: "Very dated plane. First class seat was worn, crooked, and uncomfortable. No entertainment offered. Almonds or biscuit cookies were the only food options."

Pros: "The flight left on time and landed earlier than anticipated"
Cons: "The seats were narrow and very upright"

Cons: "I didnt like that my flight was canceled and rebooked for no reason. This created me big problem in Athens that they couldnt find my ticket in delta. Also I didnt like that i had to stand and wait for 3 hours in the line because my flight was canceled but no one could let us know if there gonna be any flights within the day. I slept in the airport because i couldnt find a hotel to spend the night close to the airport. They were all full and i had no time to find one since I was waiting there for 3 hours with no informational. I slept on the floor and delta didnt even offer us a blanket. That was my worst trip ever."

Pros: "Flight was very comfortable and had a lot of space to move around"
Cons: "The gentleman indicating on the loud speakers what zones will be loading first was very rude."

Pros: "First we had a mechanical after boarding. I was rerouted through Atlanta. That flight is now delayed by 2hours. I then had to reroute to West Palm Beach instead of Ft Lauderdale. I will leave 9 hours after my original flight time and arrive 8 hours later. Just ridiculous"
Cons: "See above"

Cons: "My email read check into Aeromexico I could not check in the Aeromexico using my phone I was dropped off at the Aeromexico terminal after standing in line for half an hour I find I was in the wrong terminal I needed to be in a different terminal with Delta because Aeromexico even on my reservation read that does not fly to Tampa. I had to find a shuttle to another terminal the shuttlesare not marked it was very confusing"

Pros: "good movie selection."
Cons: "fat guy in the middle constantly moving seat barrier up to get more room."

Cons: "Took 8 hours to get from Oakland to Los Angeles. Flight delayed then cancelled at Oakland. Driven from there to San Francisco. That flight delayed by 45 minutes. Got on board and then they neede 4 people to get off the plane since it was overweight. That took another hour. Bad day of travel."

Pros: "shorter flight"
Cons: "Entertainment system is not working."

Pros: "The tv in the back of every seat makes any seat a good seat."

Pros: "Gate agent arranged flight via Salt Lake City and also gave me $15 lunch coupon for my troubles. She was awesome!"
Cons: "Dealing with West Jet to refund a mistake on the ticket purchase."

Pros: "Everything was great. Boarding agents time arrival clean planes all good"

Pros: "Ability to change planes with a 30 minute layover."

Pros: "Got from point a to pount b cheaply and fast"

Pros: "Seats are horrible, don’t even have water for free. Terrible."
Cons: "Everything"

Cons: "Good"

Cons: "Paying $45 for a carry-on bag is ridiculous as well as $50 for a checked in bag. Everything about this flight was cheap and was just dirty/uncomfortable. Will NEVER fly with spirit again."

Pros: "Delayed fight"

Pros: "Clean and simple"
Cons: "To pay for absolutely everything"

Cons: "Double booking of seats"

Pros: "Not much. The flight was fast and we got there safe."
Cons: "We were delayed 3 hours because of a smoke detector, throwing off my plans for the day. Then they were rude and tried to pretend they couldn't refund people who missed their connection or didn't want to keep waiting around for who knows how long until we could board. Bad airline"

Cons: "$58 per bag. &$ food charged at 10$,,,,Ripped off"

Cons: "It was my first time to pay for a baggage, $90.00 . Because of this, I am not happy about Spirit Airlines! :("

Cons: "Spirit is horrible- do yourself a favor and spend more to fly with another airline"

Cons: "thought that reasonable price but will realize even expensive... how come they charge $65.00 for hand carry unexpectable and never understand and no make sense please disregard spirit your compare listing...please"

Pros: "There was adequate leg room, and someone won a free ticket on our flight!"
Cons: "We were delayed by an hour, but the crew was really great about the delay. No entertainment system."

Pros: "Plenty of time to nap. In a uncomfortable chair"
Cons: "Same"

Pros: "There were no wait times for boarding"
Cons: "The seats are very very very crammed."

Pros: "Cheap, on time."

Cons: "Crew food boarding check in employ not profesional"

Pros: "The pilot did a good job."
Cons: "The bag fees were more than the flight. The travel insurance that I purchased on Spirits website with the tickets, even though they had emailed me a copy of the policy, had no record of the purchase when I called them with a question. Spirits website lists the size limits of carry on bags and the fees. They explain that it's more at the gate. I paid in advance for my laptop bag after measuring it and finding it did not meet the requirements of free carry on. At the gate I found out the laptop bag would be no charge. Spirits policy? No refunds of course. Just a $90 credit if I ever use their crappy airline in the future. I requested and paid extra for seats that were not over the wing (my wife takes pictures). We were over a wing. I paid for early boarding. It was never called ( the attendant asked for passengers with special needs). In closing, I am very disappointed that Kayak would even associate themselves with these scam artists. Low cost has limits. It's still supposed to be a service industry. Spirit is atrocious, but I became entangled with them through Kayak. I wont forget that."

Cons: "i didn't like the fact that every little detail cost money my flight started at 200. ended over 300. windsor ca to vagus i will never use spirit again and i will tell all me Friends to stay away"

Pros: "Nothing"
Cons: "When the flight was canceled, no amenities were given for lost time and opportunity. Staff was rude about this situation"

Cons: "Flight delayed then cancelled"

Pros: "The boarding was 20 minutes later than scheduled on both legs of my trip, but the upside was that once we boarded the plane, we took off within 10-15 minutes."
Cons: "Everything has an extra price with Spirit... Every. Thing."

Pros: "Not much"
Cons: "The seat selection process, seat room/comfort, and flight crew. I'm 6'-4" and was put in the last row in the corner. I asked the flight attendant to check if there were other available seats and she rudely stated no. I physically could not sit in my seat. I found a free seat and moved."

Pros: "Easy, plane was clean. Super efficient"
Cons: "That you get nickel and dimed for everything"

Pros: "Went well."

Pros: "The extra charges are obscene and it wasn't like the original flight cost was even that cheap. $45 for a Carry on. And $100 for the same carry on if you forgot to pay in advance."

Pros: "I like nothing."
Cons: "Scam! You have to pay for everything, check in, every luggage including carrying on, seat etc. I was asked to change my seat, out of goodness of my heart, I changed seat and sat were I was told to seat. Minutes later, another crew member upset told me that was not my seat and got me out of the plane until she could find a seat, and of course the crew member that caused the messed was nowhere to be found. I will never use this airline again, first and last. I don't recommend this airline and you're better off paying a little more for the airplane ticket from another airline."

Pros: "Great price! Quick and easy!"
Cons: "Seats are uncomfortable, not a big deal on a short flight."

Pros: "Nothing!"
Cons: "My flight from LA to Oakland was cancelled 3 hours before flight time. No flight available for 48 hours ! Ad to book flight on another much better airline. Also they charge 55 dollars for my 1 carry on. What a rip off! I am working on refund for trip. The inconvenience ruined my trip!!!"

Pros: "being Ontime is the most important thing on the flights"
Cons: "there was some kids making unwanted noise - so annoying & lost peace"

Pros: "price and ala carte on everything else"
Cons: "the delay arriving affected my connecting flight and resulted in my missing it"

Cons: "Flight got canceled. There were no contingency plans."

Cons: "I was in the airport 30 mins before flight and they dont let me take it. Have to pay $92 for a re-book and $50 for my lugage. I had to wait 5 hours in the airport. You can lay back in the plane because cannot recline the seats. Very unconfortable. Worst experience ever"

Pros: "Once I booked and when it was time to check in, I had to pay an extra fee for my seat - anywhere from $10 a leg to $25 a leg. All of a sudden, their price is now not a "good deal". When was Kayak or Sprint going to disclose that getting a seat is an additional fee over and above what is listed on Kayak or Sprint."

Cons: "Seats don't recline on a long flight"

Pros: "Low price"
Cons: "They charge for every single bag other than purse or small bag. $35 each way if u pay ahead... $100 at gate. Print your own boarding pass or pay an extra $10. Seat don't recline even an inch. Tray table is about 4"x8". they will try to sell you everything you get for free on any other airline. Before landing you must listen to a 10 minute pitch for their credit card. This is like a time share presentation in the sky that you cannot get away from. After baggage fees and all other things considered Southwest would have been a cheaper option"

Cons: "Nobody wants to help in difficult situation or late flights..."

Pros: "Nice people, good landing, good flight in general"
Cons: "I didn't like the repetition at the gate that they would charge $100 for oversized carryons. I think they could avoid this by making it very clear on the computer screens when you buy your ticket"

Pros: "The only thing I liked was that the airfare was very inexpensive."
Cons: "I did not like the fact that they charge you for everything that you need (even for a carry-on piece of luggage or a soda). With all the hidden costs, it is more expensive to fly on Spirit than other airlines that I have taken in the past. If you do not have any luggage, then there is not much of a problem. However, if you do have luggage, you are screwed. I do not think that I will ever fly Spirit Airlines again."

Cons: "Super expensive bag check, everything had a hidden cost"

Cons: "When purchasing our tickets we were unaware of the extra cost from luggage and seats. We had to pay for our seats and carry on luggage. It felt like one huge scam. One of the flight attendants was closing the bins and didn't even try to close the bin correctly (there was a string block the latch) she made the passenger get up and close the bin, which the passenger did easily. They are the worst airline I've ever flown with."

Pros: "From start to finish they are such a con artist deceptive hidden fees horrible customer service unorganizedthey need to be shut down"

Pros: "I have been traveling to so many places, both domestic and international with frequent flyer miles from several airlines. What made me book Spirit on a one way flight from Sfco to Lax was to make sure that my wife will get her regular dialysis treatment as soon as we land in Los Angeles. To my surprise, I did not realize only when we arrived at Sfco airport that my boarding pass was for Oakland airport, hence we missed our flight. In my desperation to make it to my wife's fixed schedule , I had to purchase another tickets for both of us, including my daughter at twice the fare $225.00 one way. The problem is this, I had specifically typed Sfco airport (meaning not Oakland) on the kayak website so in my busy travel schedule did not bother to check that it automatically gave me Oakland as departure location. I ask for a refund. Sincerely Silverio Baranda"

Pros: "They charged $50 for a very small roller suitcase. That was the only luggage I carried. It could have been easily considered as a cabin luggage free of cost, but they did not even give me a chance to speak or negotiate. I felt it was a bad customer service."

Cons: "El costo del equipaje es execivo, Y esta muy limitado por pasajero por el precio del pasaje deben ofrecer agua, sodas y jugos gratis, no vuelvo a viajar con Spirit."

Pros: "Pilot did a good job - smooth flight from that perspective"
Cons: "The staff was terrible. As we boarded, there were rules and penalties thrown out to make the experience feel more like entering prison vs. what should be a relaxing comfortable flight. On board, the staff continued to put out rules and regulations, and one point brining the book of regulations to a poor woman passenger who had paid for "first class" seats only to find out she couldn't have an infant on her lap. Initial word was she'd have to leave the plane which completely upset her. She said, "Why did you allow me to purchase this ticket if it wasn't allowed to bring my baby?" Later they said it was OK for her to go to a different seat further back for take off and landing. Later, the flight attendant took it upon himself to say that we are welcomed to purchase food on board, but that it is against federal regulations to remove the food and eat it anywhere else. Really?? Even if that is a law, is it really necessary to put all of this negative information out there? I've flown for 30 years and never had this kind of negative experience. The comfort of the seats were terrible. I'm a fit, thin person, and by the end of the flight, my bottom hurt so bad, it took 2 days to feel normal again. I am having to face a flight back to OAK on Spirit and am actually considering purchasing a different ticket to get out of ever stepping on one these planes again! I am telling every one I know NEVER to fly Spirit. This was my first experience and it was the worse flight in my entire life, filled with mean-spirited people and super uncomfortable seats."

Cons: "Just spend 50 more dollars and fly another airline. It's worth it because you'll end up spending that money (and more) anyways by paying for your carryons (45 dollars each bag EACH WAY)"

Cons: "Dried throw-up on the seat back next to me, on the floor and in my seat belt. Also had to pay for my carry on."

Pros: "Baggage...toooo expensive to check. Seats are too narrow. No reclin I ng room or leg room Everything costs...even water and it wasn't pleasant at all."

Pros: "Everything from checking to landing. It was on time, friendly staff, clean plan.it's amazing. Airlines"

Read more about Delta

Book cheap flights from Oakland to Caribbean

Recent round-trip flight deals

12/10
Thu
2 stops
Spirit Airlines
27h 33m
OAK - SJU
12/16
Wed
3 stops
Spirit Airlines
29h 14m
SJU - OAK
12/10
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Spirit Airlines
30h 59m
OAK - SJU
12/16
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Spirit Airlines
21h 35m
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12/7
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Spirit Airlines
25h 39m
OAK - STT
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29h 11m
STT - OAK
12/10
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Multiple Airlines
20h 31m
OAK - SJU
12/15
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34h 32m
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12/10
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Multiple Airlines
29h 51m
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12/16
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26h 41m
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26h 15m
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17h 05m
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12/10
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12/10
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Multiple Airlines
21h 43m
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17h 05m
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26h 30m
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20h 31m
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17h 55m
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12/7
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Delta
51h 00m
OAK - NAS
12/11
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Delta
12h 42m
NAS - OAK
Show more results

Recent one-way flight deals

1/19
Tue
2 stops
Spirit Airlines
16h 08m
OAK - SJU
1/19
Tue
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Spirit Airlines
16h 30m
OAK - SJU
12/12
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30h 59m
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28h 12m
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Multiple Airlines
17h 02m
OAK - SJU
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Spirit Airlines
39h 00m
OAK - SJU
12/16
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Multiple Airlines
13h 18m
OAK - SJU
1/18
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Multiple Airlines
28h 16m
OAK - SJU
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Spirit Airlines
26h 54m
OAK - SJU
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Multiple Airlines
28h 12m
OAK - SJU
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Spirit Airlines
45h 43m
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Multiple Airlines
25h 58m
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37h 00m
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27h 11m
OAK - SJU
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35h 32m
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Multiple Airlines
35h 32m
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Multiple Airlines
20h 51m
OAK - SJU
1/7
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Delta
15h 55m
OAK - NAS
12/28
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Spirit Airlines
15h 34m
OAK - STT
12/3
Thu
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Spirit Airlines
23h 40m
OAK - SDQ
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