$109 Find Cheap Flights from Charleston to Caribbean - 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 departing on 7/28. 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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$365
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$363
Oranjestad
Oranjestad1 stop$541
Nassau
Nassau1 stop$326
Kingston
Kingston1 stop$438
Simpson Bay
Simpson Bay1 stop$472
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown1 stop$640
George Town
George Town1 stop$469
Willemstad
Willemstad2 stops$595
Aguadilla
Aguadilla1 stop$520
Puerto Plata
Puerto Plata1 stop$705
St. John's
St. John's1 stop$753
Punta Cana
Punta Cana1 stop$365
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$363
Oranjestad
Oranjestad1 stop$541
Nassau
Nassau1 stop$326
Kingston
Kingston1 stop$438
Simpson Bay
Simpson Bay1 stop$472
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown1 stop$640
George Town
George Town1 stop$469
Willemstad
Willemstad2 stops$595
Aguadilla
Aguadilla1 stop$520
Puerto Plata
Puerto Plata1 stop$705
St. John's
St. John's1 stop$753

Book Cheap Charleston to Caribbean 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 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

Fri, Aug 28 - Mon, Aug 31
Multiple Airlines Logo
9:44 pm - 12:56 am
CHS
-
SJU
27h 12m
1 stop
Multiple Airlines Logo
5:37 pm - 9:37 am
SJU
-
CHS
16h 00m
1 stop
$257Multiple Airlines
Fri, Aug 21 - Tue, Aug 25
Multiple Airlines Logo
9:44 pm - 12:56 am
CHS
-
SJU
27h 12m
1 stop
Multiple Airlines Logo
5:37 pm - 3:28 pm
SJU
-
CHS
21h 51m
1 stop
$263Multiple Airlines
Fri, Aug 28 - Tue, Sep 1
Multiple Airlines Logo
9:44 pm - 12:56 am
CHS
-
SJU
27h 12m
1 stop
Multiple Airlines Logo
6:35 am - 6:14 pm
SJU
-
CHS
11h 39m
1 stop
$265Multiple Airlines
Sat, Jul 18 - Tue, Jul 21
American Airlines Logo
5:00 am - 5:00 pm
CHS
-
NAS
12h 00m
1 stop
American Airlines Logo
12:39 pm - 7:50 pm
NAS
-
CHS
7h 11m
1 stop
$326American Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
5:31 pm - 9:42 am
CHS
-
NAS
16h 11m
2 stops
American Airlines Logo
6:45 pm - 9:47 am
NAS
-
CHS
15h 02m
2 stops
$330American Airlines
Fri, Jul 24 - Sun, Jul 26
United Airlines Logo
6:00 am - 2:57 pm
CHS
-
NAS
8h 57m
1 stop
United Airlines Logo
3:59 pm - 10:23 am
NAS
-
CHS
18h 24m
1 stop
$333United Airlines
Thu, Aug 27 - Fri, Sep 4
JetBlue Logo
10:58 am - 10:04 am
CHS
-
SXM
23h 06m
1 stop
JetBlue Logo
3:14 pm - 7:05 pm
SXM
-
CHS
27h 51m
1 stop
$472JetBlue
Thu, Aug 20 - Fri, Aug 28
JetBlue Logo
8:14 pm - 10:04 am
CHS
-
SXM
13h 50m
1 stop
JetBlue Logo
11:20 am - 7:30 pm
SXM
-
CHS
8h 10m
1 stop
$494JetBlue
Tue, Dec 29 - Thu, Jan 7
Delta Logo
5:30 am - 12:40 pm
CHS
-
STT
6h 10m
1 stop
Delta Logo
3:10 pm - 9:46 pm
STT
-
CHS
7h 36m
1 stop
$500Delta
Sat, Sep 5 - Sat, Sep 12
United Airlines Logo
7:00 am - 7:38 pm
CHS
-
STX
12h 38m
2 stops
United Airlines Logo
9:59 am - 11:59 pm
STX
-
CHS
14h 00m
2 stops
$1,098United Airlines
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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charleston to Caribbean, 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 is December, when tickets cost $94 (return) on average. On the other hand, the most expensive months are August and September, when the average cost of round-trip tickets is $279 and $251 respectively.

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

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, 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, you should book around 3 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$109
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 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 4249 reviews
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

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

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

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

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

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.

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

The plane was not clean. Vomit was removed from seat-back pocket right in front of me. The flight attendants were rude to one another. 3 children were seated together with their parents across the aisle. The children fought physically with one slamming another’s head into the plane wall at one point. The parents were aware, but took no action to intervene. Delays occurred in Atlanta after boarding before takeoff, in the air, and in Detroit after landing (no ground crew assigned). Flight attendants offered no support for connecting flights. There were weather conditions on each end of the flight, but I didn’t mark down my ratings for these.

MSY had lots of coffee/breakfast options for morning flights. Bathrooms were clean. Lots of filling stations for water bottles. Delta flight was on time. The plane was clean. The staff was friendly and efficient.

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.

Boarded from a very small gate at LAX. Staff at gate had us line up, then waited 25 minutes to board without a word of explanation. Plane arrived on time then waited 20 minutes for a plane to vacate our gate. Majority of bags arrived after 15 minutes but it took an hour for a small number of remaining bags to be off-loaded despite my “priority” bag tag.

It's fine but Newark to Nashville was too long

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

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.

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

I liked the punctuality, the crew, and overall the whole flight

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports