$125 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 8/7. 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

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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$404
Santo Domingo
Santo Domingo1 stop$396
Montego Bay
Montego Bay1 stop$364
Oranjestad
Oranjestad1 stop$532
Nassau
Nassau1 stop$316
Kingston
Kingston1 stop$438
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$560
Bridgetown
Bridgetown1 stop$640
George Town
George Town1 stop$459
Willemstad
Willemstad2 stops$640
Aguadilla
Aguadilla1 stop$412
Puerto Plata
Puerto Plata1 stop$726
St. John's
St. John's1 stop$753
Punta Cana
Punta Cana1 stop$404
Santo Domingo
Santo Domingo1 stop$396
Montego Bay
Montego Bay1 stop$364
Oranjestad
Oranjestad1 stop$532
Nassau
Nassau1 stop$316
Kingston
Kingston1 stop$438
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$560
Bridgetown
Bridgetown1 stop$640
George Town
George Town1 stop$459
Willemstad
Willemstad2 stops$640
Aguadilla
Aguadilla1 stop$412
Puerto Plata
Puerto Plata1 stop$726
St. John's
St. John's1 stop$753

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

Sat, Aug 22 - Tue, Aug 25
Multiple Airlines Logo
8:56 pm - 12:34 am
CHS
-
SJU
27h 38m
1 stop
Multiple Airlines Logo
5:37 pm - 3:28 pm
SJU
-
CHS
21h 51m
1 stop
$214Multiple Airlines
Wed, Sep 23 - Wed, Oct 14
Multiple Airlines Logo
6:00 am - 11:57 pm
CHS
-
SJU
17h 57m
1 stop
Multiple Airlines Logo
5:12 pm - 4:03 pm
SJU
-
CHS
22h 51m
1 stop
$236Multiple Airlines
Thu, Jul 9 - Sun, Jul 12
United Airlines Logo
6:00 am - 2:57 pm
CHS
-
NAS
8h 57m
1 stop
United Airlines Logo
2:53 pm - 10:15 pm
NAS
-
CHS
7h 22m
1 stop
$316United Airlines
Mon, Aug 10 - Thu, Aug 13
American Airlines Logo
6:15 am - 7:11 pm
CHS
-
NAS
12h 56m
2 stops
American Airlines Logo
6:45 pm - 11:59 pm
NAS
-
CHS
5h 14m
1 stop
$320American Airlines
Wed, Sep 9 - Mon, Sep 14
American Airlines Logo
7:41 pm - 11:38 am
CHS
-
NAS
15h 57m
2 stops
American Airlines Logo
6:45 pm - 9:47 am
NAS
-
CHS
15h 02m
2 stops
$325American Airlines
Tue, Aug 11 - Thu, Aug 20
Delta Logo
8:10 am - 1:57 pm
CHS
-
NAS
5h 47m
1 stop
Delta Logo
3:22 pm - 11:59 pm
NAS
-
CHS
8h 37m
1 stop
$326Delta
Fri, Jul 10 - Sun, Jul 12
Delta Logo
5:10 am - 4:39 pm
CHS
-
NAS
11h 29m
1 stop
Delta Logo
6:04 pm - 12:26 am
NAS
-
CHS
6h 22m
1 stop
$333Delta
Thu, Jul 16 - Tue, Jul 21
JetBlue Logo
10:58 am - 1:59 pm
CHS
-
STT
27h 01m
2 stops
JetBlue Logo
2:53 pm - 7:19 pm
STT
-
CHS
28h 26m
3 stops
$501JetBlue
Thu, Aug 6 - Thu, Aug 13
JetBlue Logo
5:27 pm - 3:49 pm
CHS
-
STX
22h 22m
2 stops
JetBlue Logo
4:44 pm - 7:30 pm
STX
-
CHS
26h 46m
2 stops
$515JetBlue
Thu, Jul 23 - Thu, Jul 30
United Airlines Logo
7:46 pm - 12:33 pm
CHS
-
SXM
16h 47m
1 stop
United Airlines Logo
3:50 pm - 10:11 am
SXM
-
CHS
18h 21m
1 stop
$581United Airlines
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 July, when tickets cost $84 (return) on average. On the other hand, the most expensive months are August and February, when the average cost of round-trip tickets is $279 and $222 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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$125
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 13% 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.
7.9
SouthwestOverall score based on 4246 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

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.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

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.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

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.

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was old and thus the seats were not good. No cushion left whatsoever, and it all was a bit worn out.

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

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.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was very disappointed with my experience at the United Airlines baggage check. The representative was rude and unhelpful. I was required to remove approximately 1.5 pounds from my two checked bags, even though it was a very small amount over the limit. The interaction was unnecessarily unpleasant, and I expected much better customer service. I hope United will review this incident and provide additional customer service training to its staff.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

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.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

Flight left 2 hours late with no explanation as to the delay

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports