$126 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 9/25. 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 Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$425
Santo Domingo
Santo Domingo1 stop$448
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$376
Kingston
Kingston1 stop$468
Simpson Bay
Simpson Bay1 stop$558
Providenciales
Providenciales1 stop$628
Bridgetown
Bridgetown1 stop$587
George Town
George Town1 stop$529
Willemstad
Willemstad1 stop$616
Aguadilla
Aguadilla1 stop$436
St. John's
St. John's1 stop$773
Puerto Plata
Puerto Plata1 stop$760
Punta Cana
Punta Cana1 stop$425
Santo Domingo
Santo Domingo1 stop$448
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$376
Kingston
Kingston1 stop$468
Simpson Bay
Simpson Bay1 stop$558
Providenciales
Providenciales1 stop$628
Bridgetown
Bridgetown1 stop$587
George Town
George Town1 stop$529
Willemstad
Willemstad1 stop$616
Aguadilla
Aguadilla1 stop$436
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

Thu, Sep 17 - Mon, Sep 21
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
$233Multiple Airlines
Tue, Nov 3 - Wed, Nov 4
Multiple Airlines Logo
1:21 pm - 12:57 am
CHS
-
SJU
10h 36m
1 stop
Multiple Airlines Logo
6:12 pm - 4:03 pm
SJU
-
CHS
22h 51m
1 stop
$244Multiple Airlines
Tue, Nov 3 - Wed, Nov 4
Southwest Logo
1:35 pm - 12:45 am
CHS
-
SJU
10h 10m
2 stops
Southwest Logo
6:45 am - 12:50 pm
SJU
-
CHS
7h 05m
1 stop
$257Southwest
Tue, Nov 3 - Wed, Nov 4
Southwest Logo
11:00 am - 10:15 pm
CHS
-
SJU
10h 15m
2 stops
Southwest Logo
7:40 am - 5:05 pm
SJU
-
CHS
10h 25m
2 stops
$257Southwest
Thu, Sep 10 - Mon, Sep 14
Delta Logo
12:43 pm - 10:19 pm
CHS
-
SJU
9h 36m
1 stop
Delta Logo
5:59 pm - 11:59 pm
SJU
-
CHS
6h 00m
1 stop
$262Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
12:43 pm - 10:19 pm
CHS
-
SJU
9h 36m
1 stop
Delta Logo
7:00 am - 5:47 pm
SJU
-
CHS
10h 47m
1 stop
$262Delta
Thu, Sep 17 - Sat, Sep 19
United Airlines Logo
5:45 am - 12:54 pm
CHS
-
SJU
7h 09m
1 stop
United Airlines Logo
1:00 am - 9:13 am
SJU
-
CHS
8h 13m
1 stop
$262United Airlines
Thu, Sep 24 - Mon, Sep 28
United Airlines Logo
7:00 am - 1:45 pm
CHS
-
SJU
6h 45m
1 stop
United Airlines Logo
1:00 am - 9:14 am
SJU
-
CHS
8h 14m
1 stop
$272United Airlines
Tue, Aug 18 - Sat, Aug 22
JetBlue Logo
5:27 pm - 11:20 pm
CHS
-
SJU
5h 53m
1 stop
JetBlue Logo
9:22 am - 4:33 pm
SJU
-
CHS
7h 11m
1 stop
$273JetBlue
Fri, Aug 28 - Mon, Aug 31
JetBlue Logo
5:59 pm - 12:47 am
CHS
-
SJU
6h 48m
1 stop
JetBlue Logo
11:00 am - 5:06 pm
SJU
-
CHS
6h 06m
1 stop
$273JetBlue
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

$126
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 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.
8.0
SouthwestOverall score based on 4228 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

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

8.0 ExcellentSean, Jul 2026
HOU - LGB
Read more Southwest reviews

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.

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.

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.

First flight was delayed which resulted in missing our connecting. As a result class was downgraded to economy on a later flight.

My son’s suitcase was left behind at SFO and did not make the flight.

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

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.

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

The pilot was late so we didn’t take off til almost 2 hours late.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

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.

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

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports