$75 Find Cheap Flights from Charleston to Caribbean Islands

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 1/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Caribbean Islands.
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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$296
Santo Domingo
Santo Domingo1 stop$323
Montego Bay
Montego Bay1 stop$321
Oranjestad
Oranjestad1 stop$260
Nassau
Nassau1 stop$370
Kingston
Kingston1 stop$374
Simpson Bay
Simpson Bay1 stop$268
Providenciales
Providenciales1 stop$431
Bridgetown
Bridgetown2 stops$481
George Town
George Town1 stop$288
Willemstad
Willemstad1 stop$574
St. John's
St. John's1 stop$713
Aguadilla
Aguadilla1 stop$322
Punta Cana
Punta Cana1 stop$296
Santo Domingo
Santo Domingo1 stop$323
Montego Bay
Montego Bay1 stop$321
Oranjestad
Oranjestad1 stop$260
Nassau
Nassau1 stop$370
Kingston
Kingston1 stop$374
Simpson Bay
Simpson Bay1 stop$268
Providenciales
Providenciales1 stop$431
Bridgetown
Bridgetown2 stops$481
George Town
George Town1 stop$288
Willemstad
Willemstad1 stop$574
St. John's
St. John's1 stop$713
Aguadilla
Aguadilla1 stop$322

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

Mon, Jan 12 - Sat, Jan 17
Multiple Airlines Logo
5:05 pm - 3:13 am
CHS
-
SJU
9h 08m1 stop
Multiple Airlines Logo
8:00 am - 5:36 pm
SJU
-
CHS
10h 36m1 stop
$174Multiple Airlines
Mon, Feb 2 - Sat, Feb 7
Multiple Airlines Logo
5:05 pm - 5:58 pm
CHS
-
SJU
23h 53m1 stop
Multiple Airlines Logo
11:49 am - 5:39 pm
SJU
-
CHS
30h 50m2 stops
$201Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Delta Logo
1:04 pm - 11:58 pm
CHS
-
SJU
9h 54m1 stop
Delta Logo
6:15 am - 11:56 am
SJU
-
CHS
6h 41m1 stop
$221Delta
Sun, Jan 25 - Thu, Jan 29
Spirit Airlines Logo
6:35 pm - 3:35 pm
CHS
-
AUA
20h 00m1 stop
Spirit Airlines Logo
4:40 pm - 5:36 pm
AUA
-
CHS
25h 56m1 stop
$260Spirit Airlines
Thu, Jan 29 - Thu, Feb 5
Spirit Airlines Logo
6:35 pm - 2:10 pm
CHS
-
SXM
18h 35m1 stop
Spirit Airlines Logo
3:20 pm - 5:39 pm
SXM
-
CHS
27h 19m1 stop
$268Spirit Airlines
Fri, Feb 6 - Tue, Feb 10
American Airlines Logo
7:28 pm - 11:54 am
CHS
-
PUJ
15h 26m1 stop
American Airlines Logo
6:07 pm - 11:58 pm
PUJ
-
CHS
6h 51m1 stop
$319American Airlines
Wed, Jan 7 - Tue, Jan 13
American Airlines Logo
9:27 am - 2:12 pm
CHS
-
MBJ
4h 45m1 stop
American Airlines Logo
12:33 pm - 9:08 pm
MBJ
-
CHS
8h 35m1 stop
$321American Airlines
Fri, Jan 23 - Wed, Jan 28
JetBlue Logo
10:10 am - 2:03 pm
CHS
-
PLS
27h 53m1 stop
JetBlue Logo
3:11 pm - 9:20 am
PLS
-
CHS
18h 09m1 stop
$431JetBlue
Thu, Jan 29 - Thu, Feb 5
JetBlue Logo
10:10 am - 4:55 pm
CHS
-
AUA
29h 45m1 stop
JetBlue Logo
5:41 pm - 12:40 pm
AUA
-
CHS
19h 59m1 stop
$434JetBlue
Tue, Jan 20 - Fri, Jan 23
Delta Logo
6:30 am - 12:50 pm
CHS
-
PLS
6h 20m1 stop
Delta Logo
3:50 pm - 10:07 pm
PLS
-
CHS
6h 17m1 stop
$466Delta
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 $315, 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 January, when tickets cost $343 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $579 and $523 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 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$75
Most popular time to fly with an average 11% 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.
7.9
DeltaOverall score based on 8024 reviews
7.2Food
7.8Entertainment
7.9Comfort
8.5Crew
8.1Boarding
Airline reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

10.0 ExcellentAnonymous, Dec 2025
DCA - SEA
Read more Delta reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Aircraft was noisy, old and never dimmed the lights on a night flight even on business class! I flew 17 times on United and probably another 40 on other airlines United USA /Europe flights were the worst to include luggage delayed once going to europe and once coming back

Check how old the airframe is, some older ones have inoperable seat back entertainment or power.

Sitting on the runway after we land for almost two hours! Not sure if we should blame United or Just Dumpy Vance.

Hotter than Hades in August. Why, why do crews think that in the winter when we are already dressed for cold weather we need a cabin that is 82 degrees. Even the vents were blowing hot air.

Unbelievably poor service from flight attendants. They didn’t even do water service on a four hour flight. Just disrespectful.

United is an incompetent airline. They parked the plane on the tarmac for an hour after arriving because they “didn’t have a gate available” it was actually some sort of lie because as we de planed there were approximately 9 open and manned and empty gates that we walked past. Many people on the flight missed connections for the hour long sit on the tarmac. Utterly baffling and incompetent behavior from United flight ops.

Flight was delayed. De-icing took a while. When we landed had to wait for another plane to vacate our gate. Just an overall bad experience.

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

The flight was very smooth and the meal in business class was great.

The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

They cancelled our flight (and others across the country) because crews called out sick. It was a miserable experience.

They canceled the flight and didn't assist in getting a new flight on any airline. I had to spend 10 hrs in the airport after getting a ticket On Delta for twice as much. I've flown Spirit many times and this was my worst experience I've had.

The plane was supposed to leave at 12:59 Amma and another plane took us around 9:30 am. There were 7 delay announcements. We were to receive a voucher of $12 back to pay for food at any place in the airport. One passenger tried to use the voucher was denied. I did not receive the voucher for me, my son, and grandson. I went to the desk and informed them and they took my phone # and email and they told me to wait. I did and was never sent. The plane was uncomfortable, the crew was dismissive of anyone beyond the last two seats. I will NEVER fly or recommend Spirit Airlines again.

It was good. It will be nice one check Baggage cost and picking seats were free.

Sprit being a value airlines providing flights for less prices, does its basic job. Flight was on time and ride was comfortable. Its did take off and landed on time. Luggage took sometime to arrive at carousal but that could be Newark airport issue.

It ran smoothly even though we were in a high season.

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

Worst every experience travelling with Family. So much delayed while going and returning both. All airlines were time except this. not sure Spirit operational issues. No recommend Spirit. It may spoil your entire trip. Rather spent extra $ and book better airlines.

Spirit cancelled my return flight the day before travel and so I had to book a last minute flight on American Airlines.

The traffic controllers had cancelled some flights, I wish they'd done it sooner so we didn't have to sit at the airport for 3 hours.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports