$119 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 9/19. 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.
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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$420
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$374
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$326
Kingston
Kingston1 stop$476
Simpson Bay
Simpson Bay1 stop$504
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown1 stop$620
George Town
George Town1 stop$469
Willemstad
Willemstad2 stops$595
Aguadilla
Aguadilla1 stop$318
Puerto Plata
Puerto Plata1 stop$747
St. John's
St. John's1 stop$668
Punta Cana
Punta Cana1 stop$420
Santo Domingo
Santo Domingo1 stop$408
Montego Bay
Montego Bay1 stop$374
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$326
Kingston
Kingston1 stop$476
Simpson Bay
Simpson Bay1 stop$504
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown1 stop$620
George Town
George Town1 stop$469
Willemstad
Willemstad2 stops$595
Aguadilla
Aguadilla1 stop$318
Puerto Plata
Puerto Plata1 stop$747
St. John's
St. John's1 stop$668

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

Thu, Sep 10 - Mon, Sep 14
Multiple Airlines Logo
9:39 pm - 11:57 pm
CHS
-
SJU
26h 18m
1 stop
Multiple Airlines Logo
4:39 pm - 12:31 pm
SJU
-
CHS
19h 52m
1 stop
$228Multiple Airlines
Fri, Sep 11 - Mon, Sep 14
Multiple Airlines Logo
4:57 pm - 11:38 pm
CHS
-
SJU
6h 41m
1 stop
Multiple Airlines Logo
4:39 pm - 12:31 pm
SJU
-
CHS
19h 52m
1 stop
$254Multiple Airlines
Mon, Aug 24 - Thu, Aug 27
Southwest Logo
1:15 pm - 11:50 pm
CHS
-
SJU
10h 35m
2 stops
Southwest Logo
6:00 am - 3:25 pm
SJU
-
CHS
9h 25m
2 stops
$262Southwest
Tue, Aug 25 - Thu, Aug 27
Multiple Airlines Logo
4:04 pm - 12:56 am
CHS
-
SJU
8h 52m
1 stop
Multiple Airlines Logo
6:35 am - 1:04 pm
SJU
-
CHS
6h 29m
1 stop
$264Multiple Airlines
Fri, Jul 31 - Mon, Aug 3
American Airlines Logo
5:00 am - 11:39 am
CHS
-
NAS
6h 39m
1 stop
American Airlines Logo
12:39 pm - 10:03 pm
NAS
-
CHS
9h 24m
1 stop
$326American Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
5:31 pm - 9:42 am
CHS
-
NAS
16h 11m
2 stops
American Airlines Logo
6:45 pm - 9:47 am
NAS
-
CHS
15h 02m
2 stops
$330American Airlines
Thu, Oct 22 - Wed, Oct 28
Delta Logo
8:00 am - 1:41 pm
CHS
-
SDQ
5h 41m
1 stop
Delta Logo
7:49 pm - 1:46 pm
SDQ
-
CHS
17h 57m
1 stop
$408Delta
Thu, Oct 22 - Wed, Oct 28
Delta Logo
7:10 pm - 12:24 pm
CHS
-
SDQ
17h 14m
2 stops
Delta Logo
7:49 pm - 11:00 am
SDQ
-
CHS
15h 11m
1 stop
$413Delta
Fri, Aug 21 - Tue, Aug 25
JetBlue Logo
5:59 pm - 11:59 pm
CHS
-
SDQ
6h 00m
1 stop
JetBlue Logo
5:01 am - 4:33 pm
SDQ
-
CHS
11h 32m
1 stop
$425JetBlue
Fri, Aug 21 - Fri, Aug 28
JetBlue Logo
8:25 pm - 10:04 am
CHS
-
SXM
13h 39m
1 stop
JetBlue Logo
11:20 am - 7:30 pm
SXM
-
CHS
8h 10m
1 stop
$504JetBlue
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 December, when tickets cost $94 (return) on average. On the other hand, the most expensive months are August and September, when the average cost of round-trip tickets is $279 and $251 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 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

September

Cheapest flight

$119
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 12% 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.
8.0
SouthwestOverall score based on 4242 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

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.

I missed the flight because the Minneapolis flight was 49 minutes LATE, and the Boise flight LEFT 24 minutes EARLY!

Our flight was delayed multiple times and then canceled at almost 1 in the morning. We are a family of 7, traveling with 5 young children. When the flight we were supposed to fly on finally arrived after waiting all day after an international flight into JFK we were informed our flight was in need of a copilot and once they located one we would take off. Then our flight was cancelled because the copilot was over his hours and they couldn't locate another. They knew before taking off from the previous location that the copilot would be unable to fly. They could have communicated the cancellation of the flight hours in advance. Once they cancelled and the pilot and copilot got off the flight, they joked about it. While there are understandably limits on flight time for pilots, they can still handle the situation in a professional manner. The late cancellation resulted in angry passengers that required police intervention in the airport. It also occurred so late and included other delta flights that after trying 15 different hotels, we were unable to secure a hotel room, they were all booked. No rental cars were available in the area either. We ended up staying in the airport with the 5 children. We made it home after 54 hours of travel with maybe 2 hours of sleep. Our luggage was lost and had to be claimed at the airport at our final destination. This was the worst trip I have ever taken and the worst airport I have ever spent time in. I met two individuals in the airport that were kind and helpful; Tonya Maingot Williams from the can we hel desk that worked to help get us rebooked and home, as well as provide us with care bags for our extended stay in the airport. The other individual was Danielle from Buffalo Wild Wings that was so very kind when we found a place to take our family we were traveling with to eat, all 11 of us and we were able to sit down together to enjoy a meal during such a stressful time.

My flight home from Knoxville, TN, included a layover in Atlanta. I boarded the aircraft in Zone 5 and although there was limited overhead space, I was able to put my 'backpack' style roller-bag above my seat. Unfortunately, due to continued bad weather, we had to deplane. There were many people who would have missed their connection, so they rebooked. When we were re-boarding, the gate agent welcomed zone 5 and then made an announcement: All roller-bags for zone 5 passengers and higher will need to be gate checked. I promptly pushed the telescoping handle in and held my bag like a backpack. I was able to bring it on board, which was a relief. Upon entering the aircraft it became apparent that there was easily 40% open overhead space. There were audible signs of angry passengers who felt duped into checking their bags when in fact there were noticeably LESS passengers on the aircraft and TONS of overhead space. I'm not sure what kinds of parameters are used to determine when to cut off roller-bags from being brought on board, but it seemed deceptive and underhanded to have so many people get stuck checking their bags when clearly there was ample room for at least one more zone.

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.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

I bought this ticket for my daughter. She had to pay for her carry on bag to be checked. My understanding is that transatlantic flights included carry on and personal item The nickeling and diming fo legacy carriers has stooped to an all time low. So sad.

Worst service- attendants dont want to help and sat us in front of bathroom

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

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.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

Flight was fine, but not having WiFi was a major negative

Everything was excellent and I enjoyed myself. Thank for everything

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.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

It was a smooth flight and the pilot was very pleasant

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

Flight is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

Horrible. Flight was cancelled, jet blue app not working to rebook, no phone number available to call Jet Blue, 400 ish people in line for the help desk, stuck in Boston for 2 more days had to book new flight with a different airline and still not sure if I will be able to get any refund.

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

I liked the punctuality, the crew, and overall the whole flight

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports