$115 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$464
Santo Domingo
Santo Domingo1 stop$406
Montego Bay
Montego Bay1 stop$418
Oranjestad
Oranjestad1 stop$636
Nassau
Nassau1 stop$376
Kingston
Kingston2 stops$651
Providenciales
Providenciales1 stop$588
Bridgetown
Bridgetown1 stop$701
George Town
George Town1 stop$615
Aguadilla
Aguadilla1 stop$387
Puerto Plata
Puerto Plata1 stop$693
St. John's
St. John's1 stop$743
Punta Cana
Punta Cana1 stop$464
Santo Domingo
Santo Domingo1 stop$406
Montego Bay
Montego Bay1 stop$418
Oranjestad
Oranjestad1 stop$636
Nassau
Nassau1 stop$376
Kingston
Kingston2 stops$651
Providenciales
Providenciales1 stop$588
Bridgetown
Bridgetown1 stop$701
George Town
George Town1 stop$615
Aguadilla
Aguadilla1 stop$387
Puerto Plata
Puerto Plata1 stop$693
St. John's
St. John's1 stop$743
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 $520 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $683 and $665 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 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

September

Cheapest flight

$115
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 4% 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.
8.0
SouthwestOverall score based on 4214 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
Airline reviews

Every single flight I take with southwest is delayed by at least one hour. Unbelievable

2.0 MediocreMatthew, Nov 2026
Read more Southwest reviews

Every single flight I take with southwest is delayed by at least one hour. Unbelievable

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

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.

Be on time. No issues with weather etc. entirely on airline.

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.

Set on the plane for two hours before pushing off the gate due to the power source issue being fixed which was known before letting people board the plane. On top of that it was very hot as AC was not working properly. Terrible experience and limited communication provided by the crew on the status of the issue. They should let people deplane while issue is addressed instead of frying them and glued to the seats.

I am United’s newest fan. The planes are clean, the staff is so friendly and snacks are more than just old pretzel crumbles. The captain came and said hello! Truly amazing experience

1 person checking us as we boarded, left gate on time, 12.30 we are told we were held for 15 mins as other flights were waiting to take off, captain due to rain … they were having a longer gap between take offs , 3pm we took off , they went land route via New Orleans in to Florida landed at 5.45pm offered coffee and a biscuit

Service was slow Flight was very loud at back of plane

There was no internet on the flight. As an executive flying during prime business hours, having internet is critical for a smooth experience. This impacted productivity and time that will need to be spent later to do the work I could have done on flight.

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.

Plane was very comfortable,ore legroom, help yourself snack are so weren't disturbed by staff passing up and down cabin, gluten free food availability and really efficient and friendly staff . Boarding and good to time. Highly recommend t

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

Flight was fine, but I was annoyed to have to pay for luggage again. We had paid for our luggage on our first two connecting flights with SATA Azores Airlines, but had to pay for luggage again with JetBlue at JFK airport. For one trip we paid over $500 for two suitcases to travel from Azores to San Francisco.

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