$101 Find Cheap Flights from Charleston to Caribbean Islands - 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 Islands departing on 8/12. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

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$478
Santo Domingo
Santo Domingo1 stop$441
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$350
Kingston
Kingston1 stop$461
Simpson Bay
Simpson Bay1 stop$615
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown2 stops$646
George Town
George Town1 stop$458
Willemstad
Willemstad2 stops$620
Aguadilla
Aguadilla1 stop$345
St. John's
St. John's1 stop$773
Puerto Plata
Puerto Plata1 stop$760
Punta Cana
Punta Cana1 stop$478
Santo Domingo
Santo Domingo1 stop$441
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$350
Kingston
Kingston1 stop$461
Simpson Bay
Simpson Bay1 stop$615
Providenciales
Providenciales1 stop$608
Bridgetown
Bridgetown2 stops$646
George Town
George Town1 stop$458
Willemstad
Willemstad2 stops$620
Aguadilla
Aguadilla1 stop$345
St. John's
St. John's1 stop$773
Puerto Plata
Puerto Plata1 stop$760

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

Wed, Aug 26 - Mon, Aug 31
Multiple Airlines Logo
8:56 pm - 12:34 am
CHS
-
SJU
27h 38m
1 stop
Multiple Airlines Logo
5:37 pm - 9:37 am
SJU
-
CHS
16h 00m
1 stop
$234Multiple Airlines
Wed, Sep 16 - Tue, Sep 22
Multiple Airlines Logo
6:00 am - 2:55 pm
CHS
-
SJU
8h 55m
1 stop
Multiple Airlines Logo
6:05 pm - 1:24 pm
SJU
-
CHS
19h 19m
1 stop
$236Multiple Airlines
Tue, Aug 25 - Thu, Aug 27
American Airlines Logo
7:00 am - 2:38 pm
CHS
-
SJU
7h 38m
1 stop
American Airlines Logo
3:28 pm - 11:59 pm
SJU
-
CHS
8h 31m
1 stop
$262American Airlines
Mon, Aug 24 - Wed, Sep 2
American Airlines Logo
6:15 am - 6:30 pm
CHS
-
SJU
12h 15m
2 stops
American Airlines Logo
3:47 pm - 11:00 pm
SJU
-
CHS
7h 13m
1 stop
$262American Airlines
Thu, Sep 17 - Sat, Sep 26
Delta Logo
7:50 am - 4:49 pm
CHS
-
SJU
8h 59m
1 stop
Delta Logo
5:59 pm - 11:59 pm
SJU
-
CHS
6h 00m
1 stop
$272Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
9:32 am - 4:49 pm
CHS
-
SJU
7h 17m
1 stop
Delta Logo
7:00 am - 4:30 pm
SJU
-
CHS
9h 30m
1 stop
$272Delta
Thu, Aug 27 - Thu, Sep 3
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
$272Southwest
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
10:45 am - 10:00 pm
CHS
-
SJU
11h 15m
2 stops
Southwest Logo
5:55 am - 7:25 pm
SJU
-
CHS
13h 30m
1 stop
$272Southwest
Tue, Sep 22 - Tue, Sep 29
United Airlines Logo
7:00 am - 1:53 pm
CHS
-
SJU
6h 53m
1 stop
United Airlines Logo
4:55 pm - 12:15 am
SJU
-
CHS
7h 20m
1 stop
$272United Airlines
Wed, Sep 23 - Wed, Sep 30
United Airlines Logo
7:00 am - 1:53 pm
CHS
-
SJU
6h 53m
1 stop
United Airlines Logo
4:55 pm - 12:15 am
SJU
-
CHS
7h 20m
1 stop
$272United 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 $328, 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 February, when tickets cost $528 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $671 and $640 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 22% 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

$101
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Charleston to Nassau

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.
8.0
SouthwestOverall score based on 4229 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

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.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

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.

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

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.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports