$130 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$487
Santo Domingo
Santo Domingo1 stop$402
Montego Bay
Montego Bay1 stop$434
Oranjestad
Oranjestad1 stop$625
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$468
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown1 stop$660
George Town
George Town1 stop$647
Aguadilla
Aguadilla1 stop$285
St. John's
St. John's1 stop$657
Puerto Plata
Puerto Plata1 stop$725
Punta Cana
Punta Cana1 stop$487
Santo Domingo
Santo Domingo1 stop$402
Montego Bay
Montego Bay1 stop$434
Oranjestad
Oranjestad1 stop$625
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$468
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown1 stop$660
George Town
George Town1 stop$647
Aguadilla
Aguadilla1 stop$285
St. John's
St. John's1 stop$657
Puerto Plata
Puerto Plata1 stop$725
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 $488 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $650 and $618 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 24% 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

$130
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Charleston to San Juan

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 4215 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

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.

They announced a mechanical issue prior to boarding Said it was fixed, we boarded Waited Then learned it was not fixed Had to deplane and go to new gate Bought wifi on plane and it never worked

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

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.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Very Poor. Significant delays getting to Chicago and then very poor communication on delays in Chicago to Cleveland. We could have rented a car and driven there faster than the delays ended up being.

A little more friendliness from that crew of the day.

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

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.

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.

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

It was my worse flying experience. It was my first time and last time flying with Jet Blue.

The wifi didn't work and I needed to do some work. This was a business trip.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports