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Cheap Flights to Caribbean Islands

Cheapest return prices found by our users on KAYAK in the last 5 days
Kingston
Kingston2 stopsR22 968
Montego Bay
Montego Bay1 stopR21 574
George Town
George Town2 stopsR20 999
Saint Thomas Island
Saint Thomas Island1 stopR18 440
Santo Domingo
Santo Domingo1 stopR21 524
Oranjestad
Oranjestad2 stopsR20 688
Freeport
Freeport2 stopsR21 557
Kingston
Kingston2 stopsR22 968
Montego Bay
Montego Bay1 stopR21 574
George Town
George Town2 stopsR20 999
Saint Thomas Island
Saint Thomas Island1 stopR18 440
Santo Domingo
Santo Domingo1 stopR21 524
Oranjestad
Oranjestad2 stopsR20 688
Freeport
Freeport2 stopsR21 557
Booking Insights

KAYAK's insights & trends for flights to Caribbean Islands

Get data-powered insights and trends into flights to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from South Africa to Caribbean Islands?

The cheapest month for flights from South Africa to Caribbean Islands is April, when tickets cost R13 272 (return) on average. On the other hand, the most expensive months are July and August, when the average cost of round-trip tickets is R22 968 and R18 243 respectively.

How far in advance should I book a flight from South Africa to Caribbean Islands?

To get a below-average price on a flight from South Africa to Caribbean Islands, you should book around 6 weeks before departure, which saves you about 21% compared to booking last-minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

August
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly (14% more expensive on average)

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from South Africa 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 South Africa to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from South Africa to Caribbean Islands is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from South Africa to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from South Africa to Caribbean Islands 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 South Africa 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 from South Africa to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean Islands

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Caribbean Islands flight deals.

Reviews of the top 5 airlines flying to Caribbean Islands

 
Need help choosing which airline to fly with from South Africa 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.
7,3
Qatar AirwaysOverall score based on 3709 reviews
7,5Boarding
7,3Entertainment
7,9Crew
7,3Comfort
7,3Food
Airline reviews

The crew were fabulous. We travelled Doha to Miami and the crew in board we exceptional too.

10,0 ExcellentSarah, Jun 2026
Read more Qatar Airways reviews

The crew were fabulous. We travelled Doha to Miami and the crew in board we exceptional too.

Qatar was pretty OK for their services but Arangrant was awful at theirs and frankly lied to me. Qatar offers four business class fares and only three of them allow lounge access. This is a horrible policy when you pay so much for business class and shame on them for denying the simple use of their lounges for this confusion. When I requested my business class ticket with Arangrant I knew this and specifically told them I would only purchase the lowest class business seat that would still permit me lounge access on all legs of my trip. They lied to me and said I did and then I was refused this service on my return flights. I had no less than 4-8 schedule changes and got screwed by a late departure from DCA on my double connection to JNB. I lost nearly a full day on my outbound and then had little to no use of the lounges on my outbound flights. To then be denied access on my return flights made the 27 hour trip home pretty awful. Kayak should no longer work with Arangrant as they are dishonest and liars. Qatar should price all four of their business class fares to include lounge access and stop the insanity they have forced on people. My return trip home nearly ruined my entire trip to South Africa and I blame Arangrant for telling me lies and for Qatar for offering insane rules and regulations on such expensive business class fares. For the money I paid to Qatar, I did not receive the full services I was promised. I will probably never use Arangrant and their ignorant services ever again. I will question whether I ever fly on Qatar Airways again as well. When you pay so much and get such little in return, it leaves a bad taste in your mouth. Arangrant gives the whole industry a bad name and Qatar is not far behind them. I can honestly say that the wretched service and way I was treated by both have soured me on travel companies and airlines. It is bad enough that we have an idiot, felon, racist and bigoted president and administration to contend with while he has started an illegal war, I did not expect to get screwed over by Arangrant and Qatar as well. Shame on all of you.

My journey with Qatar Airways from Ahmedabad to Jacksonville on 3rd February 2026 was truly exceptional. The entire experience reflected comfort, care, and world-class service. Complimentary high-quality Wi-Fi throughout the journey was a welcome luxury, especially on a long-haul flight. The vegetarian meals were thoughtfully prepared, delicious, and served with attention to detail, along with a fine selection of snacks and beverages. What truly elevated the experience was the cabin crew — graceful, courteous, and genuinely attentive, delivering outstanding hospitality at every step. This journey perfectly showcased the premium standard Qatar Airways is known for, and it left a lasting impression. I would gladly fly with them again.

I prebooked a comfort plus seat on this flight and therefore the flight was comfy. I got the correct seat in the correct section of the plane that I have booked, that's this. Flight was comfortable. Staff were average on the flight, appearing to be rushed and short in engagement with travellers, perhaps this to maximise there rest time on the flight.

Seat experience average as they use old 777 for must flights despite full load. Qr fares are higher than other airlines for same routes so they should at least upgrade the planes . Food is average and same dishes for months on most routes I travelled at least - the Arabian rice dish “Maqboos” on every flight for months - I am sure there are other food Arabian dishes ?? It’s become boring ! Crew is always good which makes up for these things but hey confirm us what we need

As gold member there is no priority checkin. Meaning you either have to board with your zone or last with business class pax. As economy pax all the baggage bays are filled by the time you arrive

There was no phone charger, uncomfortable seats, unprofessional flight attendants, didn’t like food. Could not reserve seat in advance

You're like a poor man's Emirates Airlines. The Asian vegetarian food was awful. The entertainment selection was very limited and not contemporary at all. The seats were cramped. There was no plug for charging my phone (I refuse to plug into a USB port - A security risk). The plane itself was aged.

The flight was quite comfortable for a 12 hour flight! Food was excellent. The service was good, the entertainment was fine. All in all, one of the better long-haul flights I’ve experienced.

The food was terrible The flight attendance was sloppy and late with everything!! Never again

Crew was dismissive. Snacks and refills not offered. Poor business class experience. Bed not comfortable compared to Emirates or BA.

We were Polaris passengers and found the service poor. The food was ok but the flight attendants were not attentive and rushed the service.

It’s a service to take you from one point to another. No frills. You want it, you take it. It’s upon you to bring food, reading material, games to play, movies to watch, etc. The wifi onboard never works - so you cannot even listen to any podcasts, music, or get updated news feeds. The toilet is a mess, and a four flight does not need any hygienic interventions when people either splatter their pee all over the seats or on the floor. It’s a monopolized service and so smile and bear it.

The flight crew was fantastic. The flight attendants were incredibly considerate, kind and attentive.

Food was very very bad! Same flight from US was amazing with great food but the food prepared for the flight from Cape Town to New York was not eatable. The crew also did not smile once. They all looked like it was a shift they had not signed up for but were forced to take. :(

On time - really well operated flight. Friendly staff. Super impressed with United on this round trip.

When I purchased my ticket, I assumed it was a real ticket, as in, when I go to the airport I am guaranteed a seat. Not so. When I checked in 24 hours ahead of time, I noticed I did not have a seat assignment and my boarding pass said "Standby." I was informed at the gate that the flight was full and I may not get on that plane. I don't recall being offered the option of selecting a seat when I checked in, and apparently, for the honor of pre-selecting a seat, you must pay an additional fee. So, a ticket really isn't a ticket, it's actually a lottery and if you're lucky, you may make it on board - or you can choose to be extorted for extra money for the guarantee of a seat. It's like making reservations with the Godfather - one payment isn't enough, there's always another bribe you have to make. After the first few zones were called and I hadn't been informed of my status, I went to the gate agent and they handed me a boarding pass, for the very last row near the restrooms, in between two very large people. Apparently that was my punishment for not purchasing a seat ahead of time. Airline service has not only gotten more expensive, but the return on your money has shrunk and there is little regard for the passengers. This feels like a racket. I am not pleased, as you may have gathered.

Less packaged foods in between meals Appreciated fruits cheese platters ice cream

Flight was canceled and United offered zero assistance. Left many of us in an unsafe situation

The flight itself was fine and the pilots were great. The crew was awful - the purser WOULD NOT SHUT UP, they ran out of food, I would not serve the “beef” dinner option to my dog. The boarding process was a clusterfuck-no announcements were made about boarding groups, and when we did get on the plane, attendants were blocking the aisles taking orders for the premier lounge and not letting the poors get to their seats

The flight from American side was good, my main issue this was a part of a partner flight with gol, preventing me to use digital boarding passes and doing checking previous of the arrival to the airport.

The boarding crew was very helpful with a little special problem I had. The inflight crew - so-so.

The flight attendants were efficient and helpful. The airplane had malfunctioning equipment. Again, as was the case with my previous British Air flights, the USB port did not work. This may seem like a small detail, but in this day and age, it is important to be able to have charged electronics in order to enjoy such a long flight. Please upgrade your cabins!

The food on my AA flights was horrible, it wasn't filling either. Additionally, my bag was delayed and was damaged when delivered. However, the airline made it impossible for me to file a complaint. Had a stressful travel as multiple flights were delayed, causing unnecessary stress due to fear of missing connecting flights. Awful experience. Experience with British Airways was better than American.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

They are always late and seats was also not having working charger

The business class seats are dated and uncomfortable. The space is bare minimum and there is absolutely no privacy. For $4K, this is not what I expect.

Angela was the best fa ever. She made that 8 hour flight a breeze

After several delays and being rebooked onto a layer flight, I had to speak to three AA agents for baggage claim to get an attendant. All were in foul mode and reluctant to assist or offer any assistance.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

After we paid additional to sit in exit row, a passenger came in late with an act and sat in the exit row seat next to us. He did not pay the extra for the seat as his assigned seat was a middle seat the row before. And the did not do much to challenge him. That is not good business when you charge some people (us) additional but not others, right in front of us the customer. Not exactly looking after your customers like business schools show in countless case studies. Also on our connecting flight from Madrid to JFK, we witnessed the crew bring an already opened meal to woman sitting next to us. When she would not accept the meal, the server said that is all they had and she would have to eat. That is a blatant rejection of basic health codes. She could have gotten food poisoning if she ate the opened meal Both incidents are unacceptable. Next time the MN ame Air Europa comes up in airline selection, we will not be considering it

Need to pay for headsets, water, or any extra except air to breath.

No frills airlines. Tickets were reasonably priced for a short-term booking. But comfort is a big issue.

Food was terrible. No breakfast. Will not use this airline.

Probably will never use this air line again. Rude miserable staff. Uncomfortable seats.

The flight, the staff and the airplane were all fantastic. I highly recommend.

Impossible to check in via the App. Kept on getting emails offering upgrade. When followed through not available. Wasn't any food anyway.

Great experience, I just wish airline seats were more comfortable in general.

Totally unprofessional crew, lack of empathy and disrespectful responses. Flight got delayed for Mechanical issue for 3 hours got on the runway then back, then disembarked and just waiting with no one explaining anything and missed my connecting due to that.. the crew total lack of professionalism is totally unseen anywhere.

I was in flights from sap paulo <-> Madrid, the last one 11/15/21, That takes around 10:30 hour. Can you imagine that is served only a POOR meal after one hour of flight and nothing more??? We don’t have any service (besides in the morning a payed kart) or crew working in anything more than masks control. You need to pay for water / coffee is reasonable ? Even if you consider as low cost flights that you payed around U$ 700, courtesy and education should be showed by crew, things that Air Europe should learn to their employees on the airplane, a very rude people!!! It was not with me, but a complain for a lot people around. I have never been treated Like this before. Air Europa your journey will be short walking in this road. I, a constant traveler, will never more flight with you. I don’t need this kind of services!

They lost my luggage on my way to Namibia (I was unable to review that flight as I was in the bush/off line) It took 3 days to get my bag and I had to pay $375.00 to have it transported to my location as it was over 100 Kilometers from that Airport and the local Airlink carrier would not got that far.

Great flight, last one out the air-conditioning was far to hot and the return it was to cold and then issued blankets. On the outward bowned the headset connector didn't work properly. You had intermittent sound from the audio socket.

Terrible service especially for premium economy. Much more comfortable seats on other providers

Friendly hosts/hostesses; dinner was of acceptable, but mediocre standard

Our original booking with Kayak -our first experience -was exactly what we wanted and worked well. Updates were friendly and reassuring as were the contacts with UnderPricer so a big win-win. We learned a lot on your reliability and will definitely put you on our organisational list for the future.

It was just ok. Half the bathrooms were broke on the flight.

If they wouldn't have canceled the flight WITHOUT informing me until I looked at my ticket and saw I had 2 extra layovers in 2 different cities than the ones I paid for? That would have been nice.

Poor BA get a lot of stick and have some problems getting your bags to the same destination BUT the whole experience is very much 5 star and probably due to excellent, helpful and sooo British staff. We travelled in economy plus.

The flight was uncomfortably warm. We asked a member of the crew to adjust the temperature, and they said they would but it didn't make a noticeable difference. They really cram you into the plane, too, in economy. It was quite uncomfortable for an 11 hour flight.

The 7 hour delay in Johannesburg was extremely tiresome, with poor communication at check-in and a sad R120 voucher as compensation. All in all sitting for 10 hours on an airport was pretty bad. At arrival the baggage arrival took 2 hours. All in all, a very, very long trip.

More options for your flight to Caribbean Islands

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