$111 Find Cheap Flights from Charleston to Caribbean Islands

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 1/1. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Caribbean Islands.
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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$318
Santo Domingo
Santo Domingo1 stop$311
Montego Bay
Montego Bay1 stop$321
Oranjestad
Oranjestad1 stop$273
Nassau
Nassau1 stop$339
Kingston
Kingston1 stop$364
Simpson Bay
Simpson Bay1 stop$245
Providenciales
Providenciales1 stop$466
Bridgetown
Bridgetown1 stop$464
George Town
George Town1 stop$270
Willemstad
Willemstad1 stop$555
St. John's
St. John's1 stop$612
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla1 stop$252
Punta Cana
Punta Cana1 stop$318
Santo Domingo
Santo Domingo1 stop$311
Montego Bay
Montego Bay1 stop$321
Oranjestad
Oranjestad1 stop$273
Nassau
Nassau1 stop$339
Kingston
Kingston1 stop$364
Simpson Bay
Simpson Bay1 stop$245
Providenciales
Providenciales1 stop$466
Bridgetown
Bridgetown1 stop$464
George Town
George Town1 stop$270
Willemstad
Willemstad1 stop$555
St. John's
St. John's1 stop$612
Puerto Plata
Puerto Plata1 stop$518
Aguadilla
Aguadilla1 stop$252

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

Fri, Jan 9 - Thu, Jan 15
Multiple Airlines Logo
5:05 pm - 3:13 am
CHS
-
SJU
9h 08m1 stop
Multiple Airlines Logo
6:00 am - 5:36 pm
SJU
-
CHS
12h 36m1 stop
$160Multiple Airlines
Fri, Jan 9 - Thu, Jan 15
Multiple Airlines Logo
6:35 pm - 4:14 pm
CHS
-
SJU
20h 39m2 stops
Multiple Airlines Logo
6:00 am - 5:36 pm
SJU
-
CHS
12h 36m1 stop
$192Multiple Airlines
Thu, Feb 5 - Sat, Feb 7
Spirit Airlines Logo
6:35 pm - 9:47 am
CHS
-
SJU
14h 12m2 stops
Spirit Airlines Logo
2:59 am - 5:36 pm
SJU
-
CHS
15h 37m2 stops
$241Spirit Airlines
Mon, Feb 23 - Fri, Feb 27
JetBlue Logo
11:47 am - 7:24 pm
CHS
-
SJU
6h 37m1 stop
JetBlue Logo
11:59 pm - 10:56 am
SJU
-
CHS
11h 57m1 stop
$263JetBlue
Thu, Feb 5 - Thu, Feb 12
JetBlue Logo
1:35 pm - 8:02 pm
CHS
-
SJU
5h 27m1 stop
JetBlue Logo
6:00 am - 8:30 am
SJU
-
CHS
27h 30m1 stop
$264JetBlue
Thu, Jan 22 - Sun, Jan 25
Spirit Airlines Logo
6:35 pm - 2:27 pm
CHS
-
SDQ
18h 52m1 stop
Spirit Airlines Logo
3:32 pm - 5:36 pm
SDQ
-
CHS
27h 04m1 stop
$311Spirit Airlines
Fri, Feb 6 - Tue, Feb 10
American Airlines Logo
6:00 am - 3:45 pm
CHS
-
PUJ
8h 45m1 stop
American Airlines Logo
6:07 pm - 8:47 am
PUJ
-
CHS
15h 40m1 stop
$318American Airlines
Fri, Jan 16 - Fri, Jan 23
Delta Logo
5:25 am - 11:13 am
CHS
-
MBJ
5h 48m1 stop
Delta Logo
12:38 pm - 7:18 pm
MBJ
-
CHS
6h 40m1 stop
$321Delta
Wed, Mar 18 - Tue, Mar 31
American Airlines Logo
8:08 pm - 9:00 am
CHS
-
SDQ
12h 52m1 stop
American Airlines Logo
2:05 pm - 11:59 pm
SDQ
-
CHS
9h 54m1 stop
$322American Airlines
Sat, Feb 21 - Wed, Feb 25
Delta Logo
6:30 am - 1:33 pm
CHS
-
NAS
7h 03m1 stop
Delta Logo
1:15 pm - 7:56 pm
NAS
-
CHS
6h 41m1 stop
$389Delta
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 $320, 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 January, when tickets cost $348 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $579 and $570 respectively.

What’s the cheapest day of the week to fly from Charleston to Caribbean Islands?

The average price of all round-trip flights from Charleston to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

When flying from Charleston to Caribbean Islands, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Charleston, you’ll find the best rates on Mondays and the most expensive ones on Saturdays.

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 5 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$102
Most popular time to fly with an average 11% 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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $321 on average. Morning departures are around 6% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $455.

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.
7.9
DeltaOverall score based on 8014 reviews
8.1Boarding
7.3Food
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

2.0 MediocrePeter, Dec 2025
JFK - MEM
Read more Delta reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

Gate agent at Frankfurt was terrible. She denied PRE boarding even as it was printed on the boarding pass. Refused to look at the boarding pass and literally shouting for no reason. Frankfurt airport has horrible and rude staff who avoids trying to answer any question at all. Overall, horrible experience.

The Crew and the food was the worst I ever had in Business Class. First they told us there were no space for carry on. It was plenty of space over our 2 row seats, we had to ask to let us travel with it which was accepted. They were aware that we had to run for the connection due to the previous flight delay. Have us one hour waiting for more customers and not even offer a glass of water. Then started the service and they started to serve other passengers drinks in business and did not offer any drinks until they serve our pre ordered meal and I ask for something to drink. I had to wait until they finished to serve all passengers until Inget something. The crew was the worts I ever had for Business Class in my life.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

Flight was late - I was downgraded from first class to coach

Not good - outbound flight was delayed and missed my connection even though I got to the gate after running through the airport - the agent would not let me on because the door was closed (flight had not left). There was no notification from United - overall experience was very disappointing. Additionally, I was downgraded from first class to coach on the alternative flight

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

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

First time in a decade I threw up on the flight, turbulence was terrible!! The staff were kinda rude at times.

Boarding was good, clearly explained and efficient. Staff were helpful, I would've liked a place to get coffee that wasn't Starbucks

The most horrible flight ever not only Spirit delayed our flight 2 hours departure time for a 1 hour flight — that I could have driven FLL to TPA and spend less time on the road —- and they did the same on the return with 2-hr delay again!!! Then to top all, the rubber like and most unconfortable seats in the industry with no leg room!!! There should be an award for these kinds of companies measuring % of returning customers!!!

The flight was cancelled and Spirit said they could not rebook me on another flight for six days. They said they couldn't do anything for another six days.

Flight was on time, Newark staff, especially Nathan, very helpful, and plane crew to RDU very good without being pushy. We arrived early, and had a gentle landing.

See my last comment for the first leg. That should’ve been in here

Horrible. Arrived at my gate at 6:37 for a 6:50 flight and was denied by staff to board. Literally watched my flight leave from the window and it didn’t take off until after 7am. Tried to talk to staff and they were rude beyond compare. Will never fly with this airline again.

Our flight got rescheduled 48 hours later, the airline didn’t pay a penny for our expenses.

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports