$119 Find Cheap Flights from Charleston to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charleston to Caribbean Islands departing on 9/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Charleston to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$434
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$394
Oranjestad
Oranjestad1 stop$555
Nassau
Nassau1 stop$326
Kingston
Kingston1 stop$458
Simpson Bay
Simpson Bay1 stop$555
Providenciales
Providenciales1 stop$613
Bridgetown
Bridgetown1 stop$620
George Town
George Town1 stop$489
Willemstad
Willemstad1 stop$656
Aguadilla
Aguadilla1 stop$326
Puerto Plata
Puerto Plata1 stop$720
St. John's
St. John's1 stop$668
Punta Cana
Punta Cana1 stop$434
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$394
Oranjestad
Oranjestad1 stop$555
Nassau
Nassau1 stop$326
Kingston
Kingston1 stop$458
Simpson Bay
Simpson Bay1 stop$555
Providenciales
Providenciales1 stop$613
Bridgetown
Bridgetown1 stop$620
George Town
George Town1 stop$489
Willemstad
Willemstad1 stop$656
Aguadilla
Aguadilla1 stop$326
Puerto Plata
Puerto Plata1 stop$720
St. John's
St. John's1 stop$668

Book Cheap Charleston to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Charleston to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Charleston to Caribbean Islands

Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
9:39 pm - 11:57 pm
CHS
-
SJU
26h 18m
1 stop
Multiple Airlines Logo
4:39 pm - 12:31 pm
SJU
-
CHS
19h 52m
1 stop
$228Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
9:39 pm - 11:57 pm
CHS
-
SJU
26h 18m
1 stop
Multiple Airlines Logo
4:39 pm - 12:31 pm
SJU
-
CHS
19h 52m
1 stop
$244Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
9:39 pm - 11:57 pm
CHS
-
SJU
26h 18m
1 stop
Multiple Airlines Logo
4:39 pm - 12:31 pm
SJU
-
CHS
19h 52m
1 stop
$246Multiple Airlines
Mon, Aug 24 - Thu, Aug 27
Southwest Logo
1:15 pm - 10:50 pm
CHS
-
SJU
9h 35m
1 stop
Southwest Logo
6:00 am - 3:25 pm
SJU
-
CHS
9h 25m
2 stops
$262Southwest
Fri, Aug 7 - Wed, Aug 12
American Airlines Logo
7:33 am - 2:12 pm
CHS
-
NAS
6h 39m
1 stop
American Airlines Logo
6:45 pm - 11:59 pm
NAS
-
CHS
5h 14m
1 stop
$326American Airlines
Fri, Aug 14 - Mon, Aug 17
American Airlines Logo
6:00 am - 1:36 pm
CHS
-
NAS
7h 36m
1 stop
American Airlines Logo
3:35 pm - 11:54 pm
NAS
-
CHS
8h 19m
1 stop
$346American Airlines
Sat, Aug 29 - Sat, Sep 5
Delta Logo
6:00 am - 2:03 pm
CHS
-
STX
8h 03m
1 stop
Delta Logo
3:08 pm - 11:59 pm
STX
-
CHS
8h 51m
1 stop
$436Delta
Wed, Jan 13 - Wed, Feb 10
Delta Logo
5:30 am - 2:35 pm
CHS
-
STX
8h 05m
1 stop
Delta Logo
3:35 pm - 9:46 pm
STX
-
CHS
7h 11m
1 stop
$536Delta
Sat, Sep 5 - Sat, Sep 12
JetBlue Logo
7:56 pm - 2:43 pm
CHS
-
AUA
18h 47m
1 stop
JetBlue Logo
4:10 pm - 10:15 am
AUA
-
CHS
18h 05m
1 stop
$555JetBlue
Sun, Sep 20 - Sun, Sep 27
JetBlue Logo
7:25 pm - 2:00 pm
CHS
-
SXM
18h 35m
1 stop
JetBlue Logo
2:45 pm - 10:15 am
SXM
-
CHS
19h 30m
1 stop
$555JetBlue
Booking Insights

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

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

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $321, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charleston to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Charleston to Caribbean Islands is February, when tickets cost $521 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $671 and $641 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Charleston to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Charleston to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 29% 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

$119
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Charleston to San Juan

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Charleston 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 Charleston 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 Charleston 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 Charleston 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 Charleston to Caribbean Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Charleston to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Charleston 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.
8.0
SouthwestOverall score based on 4241 reviews
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

10.0 ExcellentTamara, Jul 2026
MCO - DEN
Read more Southwest reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

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.

Seat was too small for someone as tall as I am. I was behind an exit row making my leg room even less. There flights were delayed by multiple hours. Some weather related and others staff related. The plane was hot. Horrible experience.

The Atlanta airport had thunderstorms, which caused our flight to be delayed by multiple hours. Once we were able to board.the gate agent was rude and was trying to rush us onto the plane because the team in the plane was about to run out of hours once we were all aboard the plane they ran into an issue where the catering truck was filling up the back of the plane and they left and had to come back because they didn’t fill it up all the way, causing even more of a delay. My seat was very tight. I didn’t have a lot of legroom overall this was a miserable experience.

Flight delayed due to ground hold. Republic airways did a great job.

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.

We flew business fares. Was amazing. However, the check in didn't offer business fares preboarding which is less hectic. 8/10 due to this. Staff compared to Canadian carriers go above and beyond. Would gladly fly United again.

It was extremely hot in the cabin the entire flight, vent air was worn

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

Comfortable seating POS to IAH. Food options were satisfactory. Good seat from IAH to ANC. Food options could be better.

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.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

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

Everything was excellent and I enjoyed myself. Thank for everything

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.

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

It was a smooth flight and the pilot was very pleasant

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

Flight is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

Horrible. Flight was cancelled, jet blue app not working to rebook, no phone number available to call Jet Blue, 400 ish people in line for the help desk, stuck in Boston for 2 more days had to book new flight with a different airline and still not sure if I will be able to get any refund.

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports