$100 Find Cheap Flights from Charleston to Caribbean

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 1/26. 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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$325
Santo Domingo
Santo Domingo1 stop$323
Montego Bay
Montego Bay1 stop$340
Oranjestad
Oranjestad1 stop$324
Nassau
Nassau1 stop$403
Kingston
Kingston1 stop$384
Simpson Bay
Simpson Bay1 stop$272
Providenciales
Providenciales1 stop$487
Bridgetown
Bridgetown1 stop$482
George Town
George Town1 stop$307
Willemstad
Willemstad2 stops$514
St. John's
St. John's1 stop$607
Puerto Plata
Puerto Plata1 stop$539
Aguadilla
Aguadilla1 stop$326
Punta Cana
Punta Cana1 stop$325
Santo Domingo
Santo Domingo1 stop$323
Montego Bay
Montego Bay1 stop$340
Oranjestad
Oranjestad1 stop$324
Nassau
Nassau1 stop$403
Kingston
Kingston1 stop$384
Simpson Bay
Simpson Bay1 stop$272
Providenciales
Providenciales1 stop$487
Bridgetown
Bridgetown1 stop$482
George Town
George Town1 stop$307
Willemstad
Willemstad2 stops$514
St. John's
St. John's1 stop$607
Puerto Plata
Puerto Plata1 stop$539
Aguadilla
Aguadilla1 stop$326

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

Wed, Apr 29 - Sun, May 3
JetBlue Logo
11:00 am - 9:01 pm
CHS
-
SJU
10h 01m
1 stop
JetBlue Logo
5:01 am - 3:37 pm
SJU
-
CHS
10h 36m
1 stop
$223JetBlue
Mon, Feb 2 - Sat, Feb 7
Spirit Airlines Logo
5:05 pm - 4:22 pm
CHS
-
SJU
22h 17m
1 stop
Spirit Airlines Logo
5:50 pm - 4:10 pm
SJU
-
CHS
23h 20m
1 stop
$230Spirit Airlines
Mon, Feb 2 - Sat, Feb 7
Multiple Airlines Logo
5:05 pm - 4:22 pm
CHS
-
SJU
22h 17m
1 stop
Multiple Airlines Logo
6:11 pm - 4:10 pm
SJU
-
CHS
22h 59m
2 stops
$236Multiple Airlines
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
7:03 pm - 11:40 am
CHS
-
SJU
15h 37m
1 stop
American Airlines Logo
8:00 am - 7:22 pm
SJU
-
CHS
12h 22m
1 stop
$242American Airlines
Mon, Mar 2 - Sat, Mar 7
Multiple Airlines Logo
2:50 pm - 12:59 am
CHS
-
SJU
9h 09m
1 stop
Multiple Airlines Logo
3:59 am - 2:04 pm
SJU
-
CHS
10h 05m
1 stop
$271Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
American Airlines Logo
5:10 am - 12:08 pm
CHS
-
GCM
6h 58m
1 stop
American Airlines Logo
7:45 am - 7:22 pm
GCM
-
CHS
10h 37m
1 stop
$307American Airlines
Fri, Feb 27 - Fri, Mar 6
United Airlines Logo
6:00 am - 1:15 pm
CHS
-
GCM
7h 15m
1 stop
United Airlines Logo
2:25 pm - 11:30 pm
GCM
-
CHS
9h 05m
1 stop
$330United Airlines
Mon, Mar 2 - Mon, Mar 9
Delta Logo
6:30 am - 4:41 pm
CHS
-
PUJ
9h 11m
1 stop
Delta Logo
5:05 pm - 12:16 am
PUJ
-
CHS
7h 11m
1 stop
$339Delta
Wed, May 20 - Wed, May 27
United Airlines Logo
6:00 am - 3:10 pm
CHS
-
MBJ
10h 10m
1 stop
United Airlines Logo
4:12 pm - 9:55 am
MBJ
-
CHS
16h 43m
1 stop
$340United Airlines
Fri, Jan 30 - Wed, Feb 4
Delta Logo
5:25 am - 11:13 am
CHS
-
MBJ
5h 48m
1 stop
Delta Logo
4:45 pm - 11:55 pm
MBJ
-
CHS
7h 10m
1 stop
$342Delta
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 January, when tickets cost $363 (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 $523 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 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$100
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 11% 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.
7.9
DeltaOverall score based on 8048 reviews
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
7.9Comfort
Airline reviews

It was good because we traveled without luggage, carry on only.

8.0 ExcellentAnonymous, Jan 2026
ATL - EWR
Read more Delta reviews

It was good because we traveled without luggage, carry on only.

I usually get upgraded so my experience is usually amazing. I did not get upgraded this time - which was fine - but the wifi had issues, the monitors were going in & out, & (though not Delta's fault) one of the gentlemen next to me desperately needed a shower.

The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

Check-in, boarding and the flight from Phoenix to Houston was quick and easy. The flight from Houston to Shreveport was delayed 5 hours. It was frustrating but I think United handled it the best they could.

Some flight attendants were great others were cranky. Seats were very tight and sitting on an aisle was very hard as the carts and people walking constantly bumped shoulder and arm.

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

The professionals have excellent customer service, the seats don´t have enough space.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Bags took over and hour to come out. Delays due to wind caused rebooking.

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

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.

Liked early boarding for disabled customers. Seat comfort could have been better, would have appreciated an empty seat between my wife and I since I suffer from arthritis, neuropathy, and spinal stenosis. Also aisle seat armrest was immobile and this made it difficult to get into and out of my seat during the flight

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

It was delayed but the landing was the smoothest in a while that I’ve had.

Second time in 3 days I walked off the plane late. This time - almost an hour.

Everything went well. The flight was slightly delayed however we landed on time.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Had to pay for water if wanted it. Seats are close unless you get upgraded. Flight was fine. Will travel again with spirit.

Good! But your flight crews don’t need to ‘eat the mics’ when making announcements. If they held the mics 3 to 4 inches away from their mouths, we could understand them so much better. Otherwise, all is well.

Your flight crew and boarding area crew need to have microphone use training. They all hold the microphone right up to their mouths, way to close making understanding them almost impossible. The microphone should be held about 3 to 4 inches away from their mouths. This would provide for much better clarity through the PA system. ‘Eating the mic’ DOES NOT work.

It was the first time I flew on that airline and had a very positive experience. Nearly identical to Jetblue which consider the standard of airlines excellence.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports