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Flight Deals
Cheap Flights from Charleston to Caribbean
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook 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
Sat, Oct 31 - Wed, Nov 4
6:00 am - 5:01 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
11h 01m1 stop Tampa
8:45 am - 7:14 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
11h 29m1 stop Fort Lauderdale
$226Multiple Airlines
Sat, Oct 31 - Wed, Nov 4
6:00 am - 5:01 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
11h 01m1 stop Tampa
8:45 am - 7:14 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
11h 29m1 stop Fort Lauderdale
$230Multiple Airlines
Fri, Dec 11 - Sat, Dec 19
12:43 pm - 11:30 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
9h 47m1 stop New York John F Kennedy Intl
12:30 pm - 6:48 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
7h 18m1 stop Fort Lauderdale
$318JetBlue
Sat, Dec 12 - Sat, Dec 19
12:43 pm - 10:00 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
8h 17m1 stop New York John F Kennedy Intl
12:30 pm - 6:48 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
7h 18m1 stop Fort Lauderdale
$318JetBlue
Tue, Feb 2 - Sat, Feb 6
8:05 am - 6:25 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
9h 20m2 stops Charlotte Douglas Miami
7:22 am - 7:39 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
13h 17m1 stop Miami
$322American Airlines
Sat, Dec 12 - Thu, Dec 17
8:12 pm - 9:36 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
12h 24m1 stop Miami
3:06 pm - 12:50 amSJU San Juan Luis Munoz Marin Intl-CHS Charleston
10h 44m1 stop Miami
$322American Airlines
Tue, Jan 19 - Sat, Jan 30
5:30 am - 1:05 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
6h 35m1 stop Atlanta Hartsfield-Jackson
6:15 am - 11:26 amSJU San Juan Luis Munoz Marin Intl-CHS Charleston
6h 11m1 stop Atlanta Hartsfield-Jackson
$322Delta
Tue, Jan 19 - Sat, Jan 30
6:30 am - 1:05 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
5h 35m1 stop Atlanta Hartsfield-Jackson
6:15 am - 11:26 amSJU San Juan Luis Munoz Marin Intl-CHS Charleston
6h 11m1 stop Atlanta Hartsfield-Jackson
$322Delta
Wed, Dec 2 - Sat, Dec 5
11:00 am - 10:25 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
10h 25m2 stops Nashville Intl Tampa
5:40 am - 4:40 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
12h 00m2 stops Orlando Nashville Intl
$322Southwest
Tue, Feb 2 - Sat, Feb 6
11:00 am - 11:05 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
11h 05m2 stops Nashville Intl Baltimore/Washington
6:55 am - 5:45 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
11h 50m2 stops Tampa Nashville Intl
$322Southwest
Recent one-way flight deals from Charleston to Caribbean
Sat, Oct 31
7:52 pm - 1:25 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
17h 33m1 stop Fort Lauderdale
$115Multiple Airlines
Tue, Dec 8
1:21 pm - 7:57 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
5h 36m1 stop Tampa
$121Multiple Airlines
Tue, Jan 5
6:00 am - 7:30 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
12h 30m1 stop Miami
$161American Airlines
Fri, Dec 11
8:12 pm - 10:44 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
13h 32m1 stop Miami
$161American Airlines
Wed, Apr 7
5:30 am - 11:45 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
6h 15m1 stop Atlanta Hartsfield-Jackson
$161Delta
Thu, Dec 31
3:52 pm - 11:30 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
6h 38m1 stop Atlanta Hartsfield-Jackson
$161Delta
Thu, Nov 19
3:35 pm - 12:36 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
8h 01m1 stop Newark
$161United Airlines
Tue, Dec 8
11:00 am - 9:55 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
9h 55m2 stops Nashville Intl Orlando
$161Southwest
Thu, Nov 19
1:30 pm - 11:25 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
8h 55m1 stop Baltimore/Washington
$161Southwest
Mon, Oct 26
7:04 pm - 11:13 amCHS Charleston-MBJ Montego Bay Sangster Intl
17h 09m1 stop Newark
$223United Airlines
Recent last minute flight deals from Charleston to Caribbean
Thu, Oct 22 - Thu, Oct 29
2:13 pm - 1:53 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
11h 40m1 stop Orlando
6:15 am - 4:11 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
9h 56m1 stop Fort Lauderdale
$342Multiple Airlines
Fri, Oct 23 - Mon, Oct 26
4:57 pm - 9:55 pmCHS Charleston-SJU San Juan Luis Munoz Marin Intl
28h 58m1 stop Fort Lauderdale
7:44 pm - 8:38 amSJU San Juan Luis Munoz Marin Intl-CHS Charleston
12h 54m1 stop Orlando
$353Multiple Airlines
Thu, Oct 22 - Thu, Oct 29
4:45 pm - 1:25 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
8h 40m2 stops Baltimore/Washington Orlando
6:30 am - 4:10 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
9h 40m2 stops Orlando Nashville Intl
$511Southwest
Sat, Oct 24 - Sun, Nov 1
4:52 pm - 10:39 amCHS Charleston-PUJ Punta Cana
17h 47m1 stop Charlotte Douglas
4:51 pm - 11:59 pmPUJ Punta Cana-CHS Charleston
8h 08m1 stop Miami
$524American Airlines
Wed, Oct 21 - Wed, Oct 28
7:00 am - 4:12 pmCHS Charleston-MBJ Montego Bay Sangster Intl
10h 12m1 stop Dallas/Fort Worth
5:13 pm - 12:33 pmMBJ Montego Bay Sangster Intl-CHS Charleston
18h 20m2 stops Miami Philadelphia
$524American Airlines
Fri, Oct 23 - Mon, Oct 26
2:35 pm - 12:25 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
9h 50m2 stops Nashville Intl Orlando
6:30 am - 4:10 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
9h 40m2 stops Orlando Nashville Intl
$536Southwest
Sat, Oct 24 - Wed, Oct 28
7:00 am - 10:46 pmCHS Charleston-SDQ Santo Domingo Las Americas
15h 46m1 stop Newark
5:00 am - 1:22 pmSDQ Santo Domingo Las Americas-CHS Charleston
8h 22m1 stop Newark
$643United Airlines
Thu, Oct 22 - Mon, Oct 26
7:53 pm - 12:40 pmCHS Charleston-PUJ Punta Cana
16h 47m1 stop Washington, D.C. Dulles Intl
6:30 pm - 9:12 amPUJ Punta Cana-CHS Charleston
14h 42m1 stop Newark
$672United Airlines
Thu, Oct 22 - Fri, Oct 23
5:30 am - 11:40 amCHS Charleston-SJU San Juan Luis Munoz Marin Intl
6h 10m1 stop Atlanta Hartsfield-Jackson
2:59 pm - 10:51 pmSJU San Juan Luis Munoz Marin Intl-CHS Charleston
7h 52m1 stop Atlanta Hartsfield-Jackson
$1,767Delta
Thu, Oct 22 - Thu, Oct 29
6:30 am - 12:40 pmCHS Charleston-PLS Providenciales
6h 10m1 stop Atlanta Hartsfield-Jackson
2:05 pm - 11:59 pmPLS Providenciales-CHS Charleston
9h 54m1 stop Atlanta Hartsfield-Jackson
$2,422Delta
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.
Prices
Airlines
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 February, when tickets cost $498 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $659 and $650 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 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.
Good to know
Low season | September |
|---|---|
High season | June |
Cheapest flight | $115 |
FAQs - booking Caribbean flights
Reviews of the top 5 airlines serving from Charleston to Caribbean
7.9
SouthwestOverall score based on 4209 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews
It’s too cold like fridge and they don’t offer a blanket with expensive price
6.0 GoodJiana, Oct 2026
It’s too cold like fridge and they don’t offer a blanket with expensive price
Boarding now takes twice as long since going with assigned seats.
Smooth flights, connection, and friendly crew in the air and at the gate.
Flight was delayed again. I fly out every other weekend and lately the flight is delayed 3 out of five times 🤷🏻♀️
A List preferred boarding was nice Asked for a mask and cheerfully received Denver bag check-in is tricky. Not near other checking desk. Have to navigate to east security and up to level six for bag checkin. TSA busy and 20 minutes process thru pre lines Denver train to gates quick but one more thing to plan time for and long concourse walk to gate
Not exactly Southwest’s problem, but the new Burbank airport is not great. No restaurants open and tons of work still to be completed. Can’t believe they opened the airport in that condition.
You made me miss my connecting flight. I can not go to Cleveland on teh revised flight you are sending as I will the entire meeting. I have no option that to fly back. I hope you compensate me for the loss.
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.
Everything was great, from the flight and crew to the seating and snacks.
Two of the flight attendants were cranky and seemed like they didn’t want to be there. Not up to normal Delta standards. And our bags didn’t make flight to Italy from Amsterdam resulting in having to make a trip back to airport which cost me 75 euros.
Delta staff was exceptionally helpful and considerate. However, the first two of three flight legs were delayed making connections tentative and stressful.
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.
United, from whom we bought this code-shared flight, mid-flight canceled our tickets for the rest of our itinerary, without explanation. After long delay they tried to re-issue the tickets, but Air Canada could not find the re-issue. It finally resolved after escalation to several layers of supervisors.
Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!
The WiFi went out an hour before the flight was due to land so I did not get my money's worth.
I have been flying united for a long time but now I’m done
It's not United, but TSA security at Terminal A in Newark is a disaster and seriously makes me consider switching to flying out of JFK. The touchless TSA pre-check had a line of over 50 people and the bag screening was so slow that it limited the flow of people through the facial recognition process. It is the only airport that I frequent that has this issue and makes me reconsider whether I should fly out of Newark given the wasted time and frustration it causes. As I said, it is not a United issue but will impact United if people choose to stop utilizing Newark airport because of the poor experience.
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.
I am always very pleased with the service u receive from JetBlue employees
Your Jet Blue representative at the check in desk in Boston on Sunday morning, October 13, was unkind and unhelpful. For that reason alone I will avoid JetBlue airlines in the future. No food or beverage on the flight due to turbulence (not your fault). However I paid extra to sit in the upgraded section in the front and did not benefit from most amenities.
we used to fly with a different airline but it shut down. We had to find an alternative airline that we like in order to make domestic trips and this fits the bill. Not only is it a similar price but the customer service and the experience overall is much much better. We will be using JetBlue again.
Uncomfortable seat. No help for my disability. Staff refused to help me put my carry-on in the overhead bin. So I had to check the bag.
Terrible. Quality has gone down significantly. Plane was delayed. No instructions from the staff. Will try to avoid in the future!
The flight left unexpectedly early. Although I checked in at the gate, the crew made no attempt to contact me to inform me that what had been a delayed flight was now departing before the scheduled departure time. No announcement on the PA, no phone call. When I checked back at the gate for the delay status just before the scheduled departure time, I was told the doors were already locked and the flight had left.
Late boarding, had to check the bag even though there was space on the flight and I was I row 7
Our seats were moved for no reason. The plane was old and wifi and tv were slow. The flight was delayed over an hour for a paperwork issue. Only bright spot was the flight attendants good service.
Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.
The crew did not ensure the Evermore seats had their carry on space available. When my family and I boarded, we saw people putting their carry on suitcases in the overhead spaces above our seats and then proceed to the rear part of the plane. This resulted in us having to check our bags and being late to our meetings/events.
I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American
The first flight was delayed by an hour and a half, so we missed the second flight. They rebooked us on the later flight and I have to sit in the middle for more than 5 hours. Terrible experience. No more American Airlines.
Flight was fine, but not having WiFi was a major negative
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.
More options for your flight to Caribbean
Complete your trip to Caribbean with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Charleston
Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Charleston
Flights from all regions of Charleston to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to popular destinations in Caribbean
Flights to Antigua And Barbudafrom $743
Flights to Arubafrom $646
Flights to Barbadosfrom $953
Flights to British Virgin Islandsfrom $1,015
Flights to Cayman Islandsfrom $718
Flights to Cubafrom $336
Flights to Curaçaofrom $939
Flights to Dominican Republicfrom $425
Flights to Grenadafrom $790
Flights to Haitifrom $1,360
Flights to Jamaicafrom $465
Flights to Puerto Ricofrom $271
Flights to Saint Kitts and Nevisfrom $633
Flights to Saint Luciafrom $759
Flights to St. Maartenfrom $589
Flights to The Bahamasfrom $403
Flights to Trinidad and Tobagofrom $1,486
Flights to Turks and Caicos Islandsfrom $593
Flights to U.S. Virgin Islandsfrom $389