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Cheap Flights from Kingston to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cananonstop$271
Santo Domingo
Santo Domingononstop$268
Montego Bay
Montego Bay1 stop$819
Nassau
Nassaunonstop$689
Simpson Bay
Simpson Baynonstop$659
Providenciales
Providencialesnonstop$609
Port of Spain
Port of Spain1 stop$559
Bridgetown
Bridgetown1 stop$612
George Town
George Townnonstop$385
Willemstad
Willemstad3 stops$988
St. John's
St. John'snonstop$590
Punta Cana
Punta Cananonstop$271
Santo Domingo
Santo Domingononstop$268
Montego Bay
Montego Bay1 stop$819
Nassau
Nassaunonstop$689
Simpson Bay
Simpson Baynonstop$659
Providenciales
Providencialesnonstop$609
Port of Spain
Port of Spain1 stop$559
Bridgetown
Bridgetown1 stop$612
George Town
George Townnonstop$385
Willemstad
Willemstad3 stops$988
St. John's
St. John'snonstop$590
Booking Insights

KAYAK's insights & trends for Kingston to Caribbean Islands flights

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

What is the cheapest Kingston to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Kingston found in the last 5 days was to Punta Cana, at $310 round-trip. The most popular route is from Kingston (KIN) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $310.

Can I save money by flying with a layover from Kingston to Caribbean Islands?

No, with an average price for the route of $613, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Kingston to Caribbean Islands?

The cheapest month for flights from Kingston to Caribbean Islands is October, when tickets cost $430 (return) on average. On the other hand, the most expensive months are June and February, when the average cost of round-trip tickets is $596 and $578 respectively.

Good to know

Low season

March
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 9% increase in price.

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Kingston to Caribbean Islands 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 Kingston 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 from Kingston 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 Kingston 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 Kingston to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Kingston and Caribbean Islands per day?

    Each day, there are between 1 and 2 nonstop flights that take off from Kingston and land in Caribbean Islands, with an average flight time of 1h 49m. The most common departure time is 2:00 pm and most flights take off in the morning, while the most flights land at George Town. Each week, there are 9 flights. The most frequent day of departure is Monday, when 22% of all weekly flights depart. The fewest flights depart on a Tuesday.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Kingston to the following destinations at these prices or less: St. John's $377 one-way - $628 round-trip; Punta Cana $242 one-way - $392 round-trip; Santo Domingo $275 one-way - $444 round-trip

Reviews of the top 5 airlines serving from Kingston to Caribbean Islands

 
Need help choosing which airline to fly with from Kingston 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.
8.9
Cayman AirwaysOverall score based on 38 reviews
8.5Comfort
9.0Boarding
6.4Food
7.2Entertainment
9.4Crew
Airline reviews

Flight departed ahead of schedule and arrived ahead of schedule.

10.0 ExcellentJeffrey, Oct 2026
Read more Cayman Airways reviews

Flight departed ahead of schedule and arrived ahead of schedule.

Flight departed early and arrived early. Great flight crew and free rum punch!

Flight departed early and arrived early. Excellent, orderly boarding, ample legroom. Great crew and a very smooth flight.

There is no food or entertainment in this flight. Service was excellent.

Short flight. Excellent boarding and crew. Flight left early and arrived early!

Great flight on the Twin Otter. Early departure and early arrival. Hassle free flight.

Boarded 20 minutes late, dinner and beverages were provided but the "main" of dinner was freezing cold and had soggy lettuce. The seats were wildly uncomfortable! There was in-flight entertainment that you can access via your phone (vs. the TV on the seatback in front of you) but the wifi connection was weak and you could not actually play anything. With that said, the crew was very pleasant and friendly!

Flight crew made the flight very enjoyable as they were friendly, helpful and accommodating. Flight time was 3:40 compared to the 4:30 that was captured on our itinerary, so that was a pleasant surprise. In flight entertainment was good with plenty of selection, however some of the choices that my family tried were slow to load and stalled out a few times. We were able to restart and everyone finished watching their movies. Food was pretty basic: croissant, turkey or chicken lunch meat with Swiss cheese and a bag of Lay’s potato chips. Still a bonus considering most airlines offerings which is nothing but peanuts or a cookie.

Best experience ever. Crew were amazing, kept me informed throughout. Boarding was on time and spot on. Id book again most def

Food could have been better, and internet that allows texting/WhatsApp and other basics on the phone instead of just inflight entertainment would have been nice.

At check in I had to pay for my seat that I already paid for on purchasing my ticket. The flight was over an hour late and the plane smelt gross.

Flight ended up being longer than anticipated because we had to reroute to the Bahamas. So a hour and half flight turned into 5 hours. 0/10.

Crew were quite friendly. Food was very poor considering the price of the ticket and the flight time. Could not charge my phone due to USB charger not working..

STEWARDESSES WERE AWESOME! The food could be a bit better. Rice was SOGGY with gravy and the chicken was RUBBERY.

I was treated well in first class. I have no complaints. I will definitely fly with my favourite airline again this year.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

Blehh the airline just sucks sorry to say but the crew was nice.

Ground agent in geo need to know that the customers are the ones who pay their salary she had really bad attitude this was the check in counter agent. Also why does a pax with a working permit for another country needs a return ticket ? That don’t make no sense I have been traveling my whole life on a one way until ticket and never had any problem. Caribbean airline need to do better with the ground staff and on board service, asked for a glass of water I’m still waiting for it !

They didn’t have any headphones for the entertainment screen and their USB port didn’t accommodate a USB-C for more modern phones. The food was just ok. The staff was friendly but the seats were very uncomfortable for a full flight.

I had to run from the end of terminal one to the end of terminal two to make the connecting flight....probably a kilometer. No electric carts were available. I'm 76 and literally had to run to make the connection at the last minute. The connecting time was absolutely unrealistic. When Last Call was announced, I tried to get other Copa gate staff to call Gate 221 to let them know I was on my way, but they said no. I came within 1 minute of missing the flight.

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

horrible service, food was an embarrassment, no charging for cellphones, stay away

Did upgrade, travel in business it was great (more room I could sleep)

Seats not reclining, no vegetarian food option, no snacks. 7.5 hr flight should have been more comfortable. Luggage limits are unusually small. Will never fly Copa again and will tell friends and family to avoid this airline.

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

I loved my experience. Very safe, Very informative and very friendly.

Biggest issue was that they only had two restrooms in the back of the aircraft. Too many people for only two restrooms. The trash was overflowing and there was paper on the floor too. Long lines in the isle to use it. Food was also a bit meh. They don’t offer snacks with drinks, so you might want to buy a snack to hold you off on a longer trip, since the meals are very small.

la atencion en el avion fue excelente, la facilidad del checkin es muy buena.

Delayed fly, employees at the counter not professional and lack empathy to help, crew inside the plane very rude and unfriendly my fly was delayed for 2 hours. For being this the first time I will say if there is not other option then I will fly with this airline. One more thing, the pilot never said a wakes the whole fly but until we are about to descend. Not a welcome message the wether at the destination and time to arrival. It seems that the airplane was flying by itself without pilots. Terrible.

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

InterCaribbean seems to always be late. I do not recommend it if you have connecting flights with other airlines. The rates are the same as other regional carriers, but their aircraft are not very comfortable and are often quite hot.

Flew St Vincent to Barbados on an ATR-40 (?), seating about 60 passengers. Pretty tight in there. Flt. attendant was very friendly. Short flight - up & down in 40 minutes.

No food, no entertainment - half-hour flight (up & down) Smallest plane I’ve ever been on - maybe 60 passenger capacity?

I've had bad flights with InterCaribbean before (cancellations, no gate agents, etc.), but this one went perfectly smoothly!

Long delay. No AC on the flight from Barbados to St. Lucia.

Did not get to travel, you canceled my flight and left me stranded for the hole day, it's another day and I can't get to my destination. I will not recommend any one to this away, bad service

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental