$99 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 7/23. 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

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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$370
Santo Domingo
Santo Domingo1 stop$373
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$523
Nassau
Nassau1 stop$298
Kingston
Kingston1 stop$451
Simpson Bay
Simpson Bay1 stop$527
Providenciales
Providenciales1 stop$585
Bridgetown
Bridgetown1 stop$605
George Town
George Town2 stops$444
Willemstad
Willemstad1 stop$621
Aguadilla
Aguadilla1 stop$342
Puerto Plata
Puerto Plata1 stop$707
St. John's
St. John's1 stop$664
Punta Cana
Punta Cana1 stop$370
Santo Domingo
Santo Domingo1 stop$373
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$523
Nassau
Nassau1 stop$298
Kingston
Kingston1 stop$451
Simpson Bay
Simpson Bay1 stop$527
Providenciales
Providenciales1 stop$585
Bridgetown
Bridgetown1 stop$605
George Town
George Town2 stops$444
Willemstad
Willemstad1 stop$621
Aguadilla
Aguadilla1 stop$342
Puerto Plata
Puerto Plata1 stop$707
St. John's
St. John's1 stop$664

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, Jul 10 - Mon, Jul 13
Delta Logo
6:15 am - 11:51 am
CHS
-
NAS
5h 36m
1 stop
Delta Logo
6:04 pm - 11:19 pm
NAS
-
CHS
5h 15m
1 stop
$298Delta
Thu, Jul 23 - Thu, Jul 30
Delta Logo
5:10 am - 4:39 pm
CHS
-
NAS
11h 29m
1 stop
Delta Logo
6:04 pm - 12:26 am
NAS
-
CHS
6h 22m
1 stop
$306Delta
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
5:00 am - 2:01 pm
CHS
-
NAS
9h 01m
2 stops
American Airlines Logo
7:39 am - 6:51 pm
NAS
-
CHS
11h 12m
1 stop
$310American Airlines
Thu, Aug 20 - Tue, Aug 25
Multiple Airlines Logo
8:20 pm - 12:23 am
CHS
-
SJU
28h 03m
1 stop
Multiple Airlines Logo
6:00 am - 6:14 pm
SJU
-
CHS
12h 14m
1 stop
$314Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
6:30 pm - 1:26 pm
CHS
-
NAS
18h 56m
1 stop
American Airlines Logo
10:32 am - 11:43 pm
NAS
-
CHS
13h 11m
1 stop
$315American Airlines
Wed, Aug 5 - Tue, Aug 11
Multiple Airlines Logo
8:56 pm - 12:41 am
CHS
-
SJU
27h 45m
1 stop
Multiple Airlines Logo
6:00 am - 6:14 pm
SJU
-
CHS
12h 14m
1 stop
$325Multiple Airlines
Tue, Sep 15 - Sat, Sep 19
United Airlines Logo
5:45 am - 12:40 pm
CHS
-
PUJ
6h 55m
1 stop
United Airlines Logo
4:15 pm - 12:11 am
PUJ
-
CHS
7h 56m
1 stop
$370United Airlines
Fri, Dec 4 - Wed, Dec 9
United Airlines Logo
10:23 am - 5:25 pm
CHS
-
PUJ
6h 02m
1 stop
United Airlines Logo
5:20 pm - 9:55 am
PUJ
-
CHS
17h 35m
1 stop
$396United Airlines
Sat, Jul 4 - Thu, Jul 9
JetBlue Logo
4:37 pm - 10:35 pm
CHS
-
KIN
6h 58m
1 stop
JetBlue Logo
7:00 am - 5:39 pm
KIN
-
CHS
9h 39m
1 stop
$451JetBlue
Mon, Aug 31 - Wed, Sep 2
JetBlue Logo
5:42 pm - 9:20 pm
CHS
-
KIN
4h 38m
1 stop
JetBlue Logo
6:00 am - 4:31 pm
KIN
-
CHS
9h 31m
1 stop
$456JetBlue
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 July, when tickets cost $84 (return) on average. On the other hand, the most expensive months are August and February, when the average cost of round-trip tickets is $279 and $222 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 25% 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$99
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 8% 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 4235 reviews
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I paid for a confirmed upgraded aisle seat and was moved to a center seat in the back of the plane at the last minute.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Everything was the best it could be. Crew found me with pre- ordered food. Excellent experience!

Improve the food offerings and cabin seating. My wife would prefer to fly another airline, even with a connection for a more comfortable trip. A 737-8 should not be scheduled for a 6 hour segment, which turned into 7.5 hours due to the origin ground delay.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

Read the fine print. This was my flight home. I booked my flight for the quickest way home. Had a carry-on and a personal item. Same as my outbound flight. Apparently I needed to pre-pay extra for my carry-on. When I checked in, I was told that I had to check it. I said I’ll pay for it, and was told that this wasn’t an option anymore. They said I still had to pay $50 to check my carry-on. I told them I’ll pay whatever to just carry it in as intended. I was not allowed, so eventually I paid $50 to check my carry-on under a plane that was half full, with overhead compartments that were even less full. My white carry-on suitcase was practically destroyed getting from Idaho falls to Denver to Orange County. The low price air fair was a bait and switch. Got me to the gate, made me pay extra, then didn’t even allow me to pay for a carry on. Not to mention that I paid the $8 for WiFi that didn’t work. All to get my suitcase destroyed. I don’t think I’m going to even keep my Untied mileage plus membership and card. Apparently, membership does not have its privileges for this one.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

I flew from Santa Fe to Denver to catch a flight to London and the transfer of my luggage on arrival at Denver to the London flight worked perfectly. The crew on the ground and on board for the London flight were so friendly and efficient.

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Food is what you expect on a plane. Nothing gluten free. But that is expected. Drinks, apple juice, was fine. Seat, what I expected. Fine.

The check in agents in PHL and gate agents had to have been the rudest women that I have ever encountered; the agent weighing the bags at check in screamed continuously at all of the guests as did the woman at the gate.I have Executive Platinum status with AA and fly a lot with AA but these ladies were the absolute worst I had the displeasure to encounter!

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

The flight was delayed for more than 3 hours the flight attendant was so angry, it was my first flight with JetBlue but i don’t think I flight with them again.

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

Since we started at syr the service, crews, and flights were just excellent

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports