$115 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 9/11. 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$480
Santo Domingo
Santo Domingo1 stop$448
Montego Bay
Montego Bay1 stop$405
Oranjestad
Oranjestad1 stop$621
Nassau
Nassau1 stop$356
Kingston
Kingston1 stop$468
Simpson Bay
Simpson Bay2 stops$578
Providenciales
Providenciales1 stop$641
Bridgetown
Bridgetown1 stop$660
George Town
George Town1 stop$529
Willemstad
Willemstad1 stop$591
Aguadilla
Aguadilla1 stop$385
St. John's
St. John's1 stop$773
Puerto Plata
Puerto Plata1 stop$684
Punta Cana
Punta Cana1 stop$480
Santo Domingo
Santo Domingo1 stop$448
Montego Bay
Montego Bay1 stop$405
Oranjestad
Oranjestad1 stop$621
Nassau
Nassau1 stop$356
Kingston
Kingston1 stop$468
Simpson Bay
Simpson Bay2 stops$578
Providenciales
Providenciales1 stop$641
Bridgetown
Bridgetown1 stop$660
George Town
George Town1 stop$529
Willemstad
Willemstad1 stop$591
Aguadilla
Aguadilla1 stop$385
St. John's
St. John's1 stop$773
Puerto Plata
Puerto Plata1 stop$684

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, Sep 9 - Mon, Sep 14
Multiple Airlines Logo
6:00 am - 1:53 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
7h 53m1 stop Tampa
Multiple Airlines Logo
4:39 pm - 12:31 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
19h 52m1 stop Tampa
$238Multiple Airlines
Fri, Sep 11 - Mon, Sep 14
Multiple Airlines Logo
4:57 pm - 5:03 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
24h 06m1 stop Fort Lauderdale
Multiple Airlines Logo
4:39 pm - 12:31 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
19h 52m1 stop Tampa
$239Multiple Airlines
Fri, Aug 28 - Mon, Aug 31
American Airlines Logo
10:26 am - 11:59 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
13h 33m1 stop Charlotte Douglas
American Airlines Logo
5:10 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
6h 49m1 stop Miami
$260American Airlines
Tue, Sep 22 - Mon, Sep 28
American Airlines Logo
7:41 pm - 11:00 amCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
15h 19m2 stops Charlotte Douglas Miami
American Airlines Logo
10:16 am - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
13h 27m1 stop Miami
$260American Airlines
Sun, Sep 6 - Sat, Sep 12
United Airlines Logo
7:00 am - 3:42 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
8h 42m1 stop Houston George Bush Intcntl
United Airlines Logo
1:00 am - 9:13 amSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
8h 13m1 stop Newark
$262United Airlines
Thu, Sep 10 - Sat, Sep 12
United Airlines Logo
3:15 pm - 11:50 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
8h 35m1 stop Newark
United Airlines Logo
1:00 am - 9:13 amSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
8h 13m1 stop Newark
$262United Airlines
Tue, Jan 19 - Sat, Jan 23
Delta Logo
4:30 pm - 11:50 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
6h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:15 am - 1:47 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
8h 32m1 stop Atlanta Hartsfield-Jackson
$271Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
4:12 pm - 10:19 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
6h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 3:07 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
8h 07m1 stop Atlanta Hartsfield-Jackson
$272Delta
Thu, Nov 12 - Tue, Nov 17
Southwest Logo
7:40 am - 5:50 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
9h 10m2 stops Baltimore/Washington Orlando
Southwest Logo
6:40 am - 12:45 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
7h 05m1 stop Baltimore/Washington
$272Southwest
Sun, Sep 6 - Sun, Sep 13
Southwest Logo
7:25 am - 9:15 pmCHS  Charleston-SJU San Juan Luis Munoz Marin Intl
13h 50m2 stops Nashville Intl Orlando
Southwest Logo
5:30 am - 6:55 pmSJU  San Juan Luis Munoz Marin Intl-CHS Charleston
13h 25m1 stop Baltimore/Washington
$290Southwest
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 $327, 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 $521 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $669 and $669 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 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

Cheapest flight

$115
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 10% 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 4218 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

8.0 ExcellentDavid, Aug 2026
Read more Southwest reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

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.

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.

Stewardess was not accommodating when I requested a second drink.

The morning calzone was less than impressive and we ended up with heartburn

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.

the seat has a problem. the back had a hole.

The back to back mechanical delays from Denver to San Diego and then on my return flight from Denver to Great Falls it added extra time both ways

Really old place. Not as clean as it should be, tray tables needed better cleaning. The items, trays and some other items need to b6 engineered. Anything task you or crew may do is incredibly load, seriously engineer for quiet smooth, easy. Just opening and closing the tray table is actually dangerous and can easily injure a finger. I'm sure it happens as it happened to me! First time I used United and likely will be the last!

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

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.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The flight was on time the crew was courteous that makes for a good flight.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports