$100 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 3/3. 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$312
Santo Domingo
Santo Domingo1 stop$267
Montego Bay
Montego Bay1 stop$281
Oranjestad
Oranjestad1 stop$311
Nassau
Nassau1 stop$325
Kingston
Kingston1 stop$438
Simpson Bay
Simpson Bay1 stop$324
Providenciales
Providenciales2 stops$434
Bridgetown
Bridgetown1 stop$518
George Town
George Town1 stop$289
Willemstad
Willemstad3 stops$538
St. John's
St. John's1 stop$653
Puerto Plata
Puerto Plata1 stop$569
Aguadilla
Aguadilla1 stop$259
Punta Cana
Punta Cana1 stop$312
Santo Domingo
Santo Domingo1 stop$267
Montego Bay
Montego Bay1 stop$281
Oranjestad
Oranjestad1 stop$311
Nassau
Nassau1 stop$325
Kingston
Kingston1 stop$438
Simpson Bay
Simpson Bay1 stop$324
Providenciales
Providenciales2 stops$434
Bridgetown
Bridgetown1 stop$518
George Town
George Town1 stop$289
Willemstad
Willemstad3 stops$538
St. John's
St. John's1 stop$653
Puerto Plata
Puerto Plata1 stop$569
Aguadilla
Aguadilla1 stop$259

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

Sat, Apr 11 - Sat, Apr 18
Spirit Airlines Logo
8:07 am - 3:28 pm
CHS
-
STT
7h 21m
1 stop
Spirit Airlines Logo
4:40 pm - 10:41 pm
STT
-
CHS
6h 01m
1 stop
$183Spirit Airlines
Wed, Apr 1 - Wed, Apr 8
Spirit Airlines Logo
8:07 am - 6:55 pm
CHS
-
SJU
10h 48m
1 stop
Spirit Airlines Logo
12:55 pm - 10:13 pm
SJU
-
CHS
9h 18m
1 stop
$188Spirit Airlines
Wed, Apr 1 - Wed, Apr 8
Spirit Airlines Logo
8:07 am - 6:55 pm
CHS
-
SJU
10h 48m
1 stop
Spirit Airlines Logo
12:55 pm - 10:13 pm
SJU
-
CHS
9h 18m
1 stop
$199Spirit Airlines
Mon, Feb 23 - Fri, Feb 27
American Airlines Logo
7:03 pm - 12:55 pm
CHS
-
SJU
16h 52m
1 stop
American Airlines Logo
8:40 am - 11:51 pm
SJU
-
CHS
16h 11m
1 stop
$222American Airlines
Thu, Feb 19 - Mon, Feb 23
JetBlue Logo
9:20 am - 4:59 pm
CHS
-
NAS
7h 39m
1 stop
JetBlue Logo
6:04 pm - 1:54 pm
NAS
-
CHS
19h 50m
1 stop
$325JetBlue
Mon, May 4 - Fri, May 8
Delta Logo
5:20 am - 11:35 am
CHS
-
PUJ
6h 15m
1 stop
Delta Logo
1:10 pm - 10:56 pm
PUJ
-
CHS
9h 46m
1 stop
$339Delta
Thu, Feb 26 - Mon, Mar 2
American Airlines Logo
6:36 pm - 12:21 pm
CHS
-
MBJ
17h 45m
1 stop
American Airlines Logo
2:33 pm - 11:59 pm
MBJ
-
CHS
9h 26m
1 stop
$340American Airlines
Mon, Mar 2 - Mon, Mar 9
Delta Logo
5:27 am - 4:21 pm
CHS
-
PUJ
9h 54m
2 stops
Delta Logo
3:50 pm - 12:16 am
PUJ
-
CHS
8h 26m
1 stop
$343Delta
Mon, Mar 2 - Mon, Mar 9
JetBlue Logo
2:25 pm - 4:27 pm
CHS
-
NAS
26h 02m
1 stop
JetBlue Logo
5:32 pm - 1:54 pm
NAS
-
CHS
20h 22m
1 stop
$363JetBlue
Fri, Apr 17 - Mon, Apr 20
United Airlines Logo
6:00 am - 4:05 pm
CHS
-
PLS
10h 05m
1 stop
United Airlines Logo
2:35 pm - 11:59 pm
PLS
-
CHS
9h 24m
1 stop
$502United Airlines
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 $306, 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 October, when tickets cost $371 (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 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 19% 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 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.
7.9
DeltaOverall score based on 8132 reviews
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
7.8Entertainment
Airline reviews

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

2.0 MediocreAlparda, Feb 2026
BOS - ICN
Read more Delta reviews

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

Although our flight was delayed the overall boarding process was very smooth and the crew was accommodating.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

It would be nice to have some low carb options in the snacks.

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

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

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.

Everything was good. On time, boarding fast, flight attendants friendly.

Great, but seats are terrible. Way too cramped for any human.

Spirit has always and will always stink. Absolute worst airline around.

It was smooth sailing snags we had a really smooth landing and a great flight!

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

Flight was cancelled. But kayak thought it was still on time.

For the cost you can't e too critical, but the inablitiy to recline the seat and minimal cushioning in the seats made for a less than comfortable flight. Other than that we had an ealry departure and arrival, boarding was smooth.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports