$137 Find Cheap Flights from Charleston to Caribbean - Compare and Save

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Cheap Flights from Charleston to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$465
Santo Domingo
Santo Domingo1 stop$402
Montego Bay
Montego Bay1 stop$425
Oranjestad
Oranjestad2 stops$622
Nassau
Nassau1 stop$404
Kingston
Kingston1 stop$611
Providenciales
Providenciales1 stop$648
Bridgetown
Bridgetown1 stop$661
George Town
George Town1 stop$576
Aguadilla
Aguadilla1 stop$302
Puerto Plata
Puerto Plata1 stop$697
St. John's
St. John's1 stop$698
Punta Cana
Punta Cana1 stop$465
Santo Domingo
Santo Domingo1 stop$402
Montego Bay
Montego Bay1 stop$425
Oranjestad
Oranjestad2 stops$622
Nassau
Nassau1 stop$404
Kingston
Kingston1 stop$611
Providenciales
Providenciales1 stop$648
Bridgetown
Bridgetown1 stop$661
George Town
George Town1 stop$576
Aguadilla
Aguadilla1 stop$302
Puerto Plata
Puerto Plata1 stop$697
St. John's
St. John's1 stop$698
Booking Insights

KAYAK's insights & trends for Charleston to Caribbean flights

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

What is the cheapest month to fly from Charleston to Caribbean?

The cheapest month for flights from Charleston to Caribbean is February, when tickets cost $498 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is $649 and $645 respectively.

How far in advance should I book a flight from Charleston to Caribbean?

To get a below average price on the flight from Charleston to Caribbean, you should book around 3 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

September

Cheapest flight

$137
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 5% increase in price.
Flight from Charleston to Nassau

FAQs - booking Caribbean flights

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

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

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

Reviews of the top 5 airlines serving from Charleston to Caribbean

 
Need help choosing which airline to fly with from Charleston 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.
7.9
SouthwestOverall score based on 4215 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

2.0 MediocreBrittney, Oct 2026
Read more Southwest reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

Your computers were down and took a long time to check baggage

Southwest has lost most of what made it special. The flight attendants all used to seem fun and like they were having fun. Now they seem just miserable. They do NOT seem happy to give you your pretzels and drinks. They stick it in your hand or on your tray like it's an annoyance. They bark safety instructions at you. It's not just this flight but the last few SW flights I've had to SNA and SAN as well and it's not just me. I've informally surveyed my colleagues (business and leisure travelers) and these feelings are consistent. The tickets are similarly priced to other carriers and the seat assignments make boarding slower. The free luggage and free ability to change flights is still a differentiator. You lose that and there's virtually nothing special left.

Flight attendant skipped about 6 rows for drink service. I got a side eye when I asked for a drink - like it was an inconvenience or my mistake. He shouldn't be on a flight if he doesn't like his job and doesn't have customer service first attitude.

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

They did not fix the wifi that they knew was an issue on an earlier flight. The flight was filled with business people that were clearly frustrated not being able to work. That can’t happen on a 3 1/2 hour flight. Would rather have been delayed a bit.

The WiFi did not work three hours of productivity lost. 15 people from the firm were on the flight. Loss of revenue

Very good. Exactly what I expected. We did have a slight delay.

I think Southwest can offer a whole can of beverage instead of such a small cup

I like the boarding procedure. Handle the bird strike issue well.

On time, quick boarding, so nice of them to honor active and retired military with early boarding. Attendants were nice . Plane was clean. A bit crowded like all flights.

Two of the flight attendants were cranky and seemed like they didn’t want to be there. Not up to normal Delta standards. And our bags didn’t make flight to Italy from Amsterdam resulting in having to make a trip back to airport which cost me 75 euros.

Delta staff was exceptionally helpful and considerate. However, the first two of three flight legs were delayed making connections tentative and stressful.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

I just can’t understand why are you sell to many tickets ???? We had to wait 2 hours before 13 people from our flight take money and go to next day flight!

The only real hiccups in the flight were things beyond Delta’s control - turbulence which delayed food service and a departure delay caused by some VIP plane which stopped all departures and landings for 30 minutes - and was never explained to us by the crew. Otherwise good flight. I would fly Delta again.

The plane was frigid, and leaked water from the ceiling all over me and my seat.

A couple flight attendants in business class had bad attitudes and provided poor service. They did provide drinks or refill drinks. They talked to certain passengers for long periods of time and ignored others.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

1) United economy seats barely recline. 2) I have yet to get United WiFi to work, after numerous flights.

Flight attendants need to know their plane. Seated in first row yesterday. The seat had about a 1 inch recline that was not adjustable. I don't appreciate being awakened to raise a seat that can't go any further forward and such a small recline is either irrelevant or the plane needs to be repaired. Not the way to treat any customer and especially the ones who have paid that level of money for the seats.

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

The attendant were friendly. I suggest you have a medical attendant on board every flight so that in case someone is sick , he/she will help them.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

The crew did not ensure the Evermore seats had their carry on space available. When my family and I boarded, we saw people putting their carry on suitcases in the overhead spaces above our seats and then proceed to the rear part of the plane. This resulted in us having to check our bags and being late to our meetings/events.

Crew was friendly. Free headphones would be nice. Free new movies would be better.

Diana at the gate was unhelpful which was fine, but she was also rude which I did not appreciate at all.

Multiple delays, poor communication, dismissive staff, chaotic boarding, broken seat back entertainment. Not really much to like.

The crew was friendly and helpful. The entertainment system in my row did not work for movies and TV shows and the Direct TV cut off in parts and stopped showing the baseball playoff game.

Non-stop commercials were frustrating when trying to view direct TV

Forced to check bag, even though plenty of space in overhead bins. Did not appreciate having to wait at baggage claim to retrieve suitcase.

Great. I was in mint class. Security was spectacular. A lot of room on the flight! And the WiFi worked this time- it didn’t work the last time and I am on a business trip so that was a problem.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American

The first flight was delayed by an hour and a half, so we missed the second flight. They rebooked us on the later flight and I have to sit in the middle for more than 5 hours. Terrible experience. No more American Airlines.

Flight was fine, but not having WiFi was a major negative

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

Would have thought that they would gas up plane before everyone got on board

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

American switched my flight to a 5 hour layover then cancelled my whole reservation with no notice and refused refund. Won’t fly with them again.

We sat on runway for an 1 hour because they were short handed at key west airport was not fun

The WiFi and app don’t work as easily as other airlines

Late. Then next flight was an hour late due to mx.

More options for your flight to Caribbean

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