$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$444
Santo Domingo
Santo Domingo1 stop$402
Montego Bay
Montego Bay1 stop$405
Oranjestad
Oranjestad2 stops$622
Nassau
Nassau1 stop$404
Kingston
Kingston1 stop$526
Providenciales
Providenciales1 stop$605
Bridgetown
Bridgetown1 stop$680
George Town
George Town1 stop$565
Aguadilla
Aguadilla1 stop$282
St. John's
St. John's1 stop$702
Puerto Plata
Puerto Plata2 stops$664
Punta Cana
Punta Cana1 stop$444
Santo Domingo
Santo Domingo1 stop$402
Montego Bay
Montego Bay1 stop$405
Oranjestad
Oranjestad2 stops$622
Nassau
Nassau1 stop$404
Kingston
Kingston1 stop$526
Providenciales
Providenciales1 stop$605
Bridgetown
Bridgetown1 stop$680
George Town
George Town1 stop$565
Aguadilla
Aguadilla1 stop$282
St. John's
St. John's1 stop$702
Puerto Plata
Puerto Plata2 stops$664
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 $496 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $645 and $634 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 6% increase in price.
Most popular time to fly with an average 6% 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 4200 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Unfortunately, I left my headphone's case in the bag of the front seat. I was seating on 9C. Hopefully the found it and I can get it back. I have not been able to get in contact with Southwest. Other than that, everything went fine.

8.0 ExcellentSolon Leonel, Sep 2026
Read more Southwest reviews

Unfortunately, I left my headphone's case in the bag of the front seat. I was seating on 9C. Hopefully the found it and I can get it back. I have not been able to get in contact with Southwest. Other than that, everything went fine.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wifi was terrible. I couldn't get any work done on the long flight

It's a shame that SW was previously my preferred carrier until they started imposing all these fees (luggage, seats,etc) and pulling back on other perks. I only flew with them this time due to time frame I needed to be at destination. Wasn't provided gate info during check-in, Gate info wasn't displayed at airport until last minute, gate info didn't match what SW personnel announced at fate. Kind of a mess.

Flight was fine. Only thing was flight was delayed nearly 2 hours. Flight was originally scheduled to depart at 7:50pm but didn't depart until 9:50pm. I got home around midnight. It was later than desired and I had to get up early next day to take kids to practice. I have noticed that last flight of day on West Coast for Southwest always tend to have delays.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

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.

Crew completed ignored our aisle when giving snacks and coffee

The seats were great and the service was even better. Thank you!

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.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

The united employees at the gate treated me very rudely and called me nefarious

The food was horrible. There was no. Wifi, and it was just terrible from bangkok to d. C

My flight got cancelled. Couldn’t get my luggage. It arrived at my destination ahead of me. I didn’t get my preordered meal. Had to spend the night in the airport.

The crew was good, the WiFi was amazing, but the plane was meh. Uncomfortable first class, not enough room for baggage. My stuff ended up being behind my seat, so I had to sit on the plane for 20 minutes before I could get to it after landing.

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.

Nice plane, with TV, comfortable seats and leg room. Updated regularly on time changes

Overall, it was a fantastic experience had no movies up charge for everything haven’t flown in many many years. Crew is fantastic. Flight was good overall great experience.

My sons tv wasn’t working and they didn’t give him a kids meal I have to request it prior and no one told me!!! Then the 2nd flight they split us up. My two year old can’t sit alone on the plane hello?????

What's not to like? Value?definitely. Every JetBlue member was extremely friendly on this flight. Very very nice new-ish aircraft,plenty of room. GOOD coffee. Entertainment,I didn't need it,but I think its available. What to do better? Well,there's nothing we can do about the other people, unbelievable how some folks are operating. Just don't allow people to lug all their stuff onto the aircraft. 1 bag. That's it. Be easier for you too. I personally would enjoy more options in schedule. One flight in and out a day is warranted given the local,I understand, but the times are inconvenient. Again, I completely understand why it is that way,It would however be great to have different options.

Had to wait over an hour in line for a Jet Blue agent to appear at the the counter. Ended up a customer service agent from another airline lines helped to check us in, and boarding pass,

Thought the economy premium experience would match that of the Amsterdam to Boston flight. Aircraft was older: chair didn’t lean back. I had to buy a blanket, which on the flight over was complimentary. Flight crew seemed disinterested all around.

I propose enhancing the legroom across the entire cabin seating area and expanding the snack selection. The airline companies should prioritize customer needs over the extravagant and unjustified salaries of upper management.

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

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