$239 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 8/27. 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 Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$468
Montego Bay
Montego Bay1 stop$402
Nassau
Nassau1 stop$420
Punta Cana
Punta Cana1 stop$468
Montego Bay
Montego Bay1 stop$402
Nassau
Nassau1 stop$420

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

Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:55 pm - 2:38 pm
CRW
-
SJU
19h 43m
2 stops
American Airlines Logo
6:00 am - 6:25 pm
SJU
-
CRW
12h 25m
2 stops
$278American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
5:14 pm - 11:43 pm
CRW
-
SJU
6h 29m
1 stop
American Airlines Logo
6:00 am - 6:25 pm
SJU
-
CRW
12h 25m
2 stops
$278American Airlines
Sat, Aug 22 - Sun, Aug 30
American Airlines Logo
6:55 pm - 2:38 pm
CRW
-
SJU
19h 43m
2 stops
American Airlines Logo
6:00 am - 6:25 pm
SJU
-
CRW
12h 25m
2 stops
$336American Airlines
Sat, Aug 22 - Sun, Aug 30
American Airlines Logo
5:14 pm - 11:43 pm
CRW
-
SJU
6h 29m
1 stop
American Airlines Logo
6:00 am - 6:25 pm
SJU
-
CRW
12h 25m
2 stops
$336American Airlines
Tue, Aug 25 - Tue, Sep 1
Delta Logo
2:52 pm - 10:29 pm
CRW
-
SJU
7h 37m
1 stop
Delta Logo
2:59 pm - 11:31 pm
SJU
-
CRW
8h 32m
1 stop
$342Delta
Mon, Oct 19 - Fri, Oct 23
Delta Logo
6:00 am - 1:49 pm
CRW
-
SJU
7h 49m
1 stop
Delta Logo
12:50 pm - 11:30 pm
SJU
-
CRW
10h 40m
1 stop
$352Delta
Mon, Aug 17 - Fri, Aug 21
Multiple Airlines Logo
10:59 am - 12:41 am
CRW
-
SJU
13h 42m
1 stop
Multiple Airlines Logo
5:37 pm - 1:42 pm
SJU
-
CRW
20h 05m
2 stops
$392Multiple Airlines
Fri, Sep 4 - Tue, Sep 8
Multiple Airlines Logo
10:59 am - 12:56 am
CRW
-
SJU
13h 57m
1 stop
Multiple Airlines Logo
8:43 pm - 2:03 pm
SJU
-
CRW
41h 20m
2 stops
$399Multiple Airlines
Mon, Oct 19 - Fri, Oct 23
Delta Logo
6:00 am - 11:51 am
CRW
-
MBJ
6h 51m
1 stop
Delta Logo
1:16 pm - 11:30 pm
MBJ
-
CRW
9h 14m
1 stop
$402Delta
Mon, Jan 25 - Mon, Feb 8
United Airlines Logo
5:59 pm - 12:07 pm
CRW
-
MBJ
18h 08m
2 stops
United Airlines Logo
2:48 pm - 4:51 pm
MBJ
-
CRW
26h 03m
1 stop
$463United 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 $324, 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 September, when tickets cost $0 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is $1,610 and $948 respectively.

Good to know

Low season

March

Cheapest flight

$239
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 50% lower on average.
Flight from Charleston to Punta Cana

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 airlines flying 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.
7.8
DeltaOverall score based on 8497 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.2Food
7.8Entertainment
Airline reviews

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.

2.0 MediocreAidan, Jul 2026
RDU - BOS
Read more Delta reviews

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.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

The flight was done by SkyWest only WIFI no entertainment center are available on the CRJ

Your survey needs a N/A option. I didn’t use the entertainment or eat food.

The flight was over 2 hours late.. once we finally got boarded things were fine

Poor communication, we sat on the plane for an hour before pushing back. They were oversold and with a full plane kept looking for someone to step off for someone else to board. So after an hour wait at the gate we missed our departure window and proceeded to spend an additional hour on the tarmac waiting for a refiled flight plan according to the pilots. Occasional updates, somewhat insensitive crew to passengers needing to use the lavatory (it was 2 hrs beyond what anyone expected). Overall just poor execution...especially when the flight was listed as "arriving early" up until about 30 minutes past our departure time.

No tv. No free wifi. They need to ipgrade these planes - especially on a 2 hour flight.

Flight was delayed for about an hour but overall good experience

Staff is friendly and helpful but flight was delayed by one hour from Detroit, making for tight window in Toronto to clear Canada Customs and pass through security screening in order to get to connecting flight on time.

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

This flight 1810 on 7/30 from EWR to DFW got 4 hours delay. this round trip experience is bad, my AA flight 618 from DFW to EWR on 7/28 was redirected to PIT and totally delayed about 9 hours due to mixed of weather and AA IT outage and then on the way back delayed for 4 hours. Lucky, i changed my flight to UA on the way back. i don't like AA anymore. i will consider other airline options in the future.

Bad experience going to DFW with an IT outage then bad on the way back with a nearly 5 hour delay that’s started as maintenance then caused us to wait further due to weather - which would not have happened if we had left on time.

IT issues created a mess had you change my flight and your system never changed it

Horrible experience flying with American. Flight was delayed due to inbound flight delay. Fine, it happens. Then, we were delayed an additional almost 30 minutes due to the paperwork for departure having a "clerical error." Then, upon landing at the destination airport we were stuck on the plane for an HOUR after we landed and pulled up to the gate because apparently there was another plane. An hour waiting for the gate 12:30 AM when the flight has already been delayed due to operational error feels like a complete failure of the ability to do the one thing they need to do apart from actually have the plane takeoff and land. Very disappointing.

It was a 3 hour flight from Dallas to Missoula. The aircraft did not have power plugs, internet or in-flight entertainment. When boarding, one flight attendant was "somewhere in the airport" so delayed the boarding process (not coming from another flight) although we did take off on time and landed early. In flight there was little to no service - we got the standard beverage but no real connection with the crew which feels unusual for a 3 hour flight. A passenger needed help stowing her bag and got no assistance, and actually some passive aggressive comments from the flight attendants about "she needs to remove the extender" and "she'll have to find a place for it". I have seen others be helpful and put a bag in the closet, or support assistance as the boarding door was already closed. Just not a great experience considering the cost of my round trip ticket {$1000}.

Disorganized boarding. Mandatory to gate check bags. Curt flight staff. No space for cabin bag, even when I was in first class.

On time departure & early arrival. Made a long day much better.

The ground closures and flight delays were unwelcome. I think the captain did what he could to manage expectations for the delays, but the stress level increasing in the cabin was palpable with every announcement. It may be obvious to those who fly frequently, but if the ground is closed for us to get to a gate, it's also closed for connecting flights to leave. Other passengers were so stressed they were rude. A bit further explanation could have helped.

Horrible. No AC. No Air inside the plane. We had to deplane twice! It is late almost 5 hrs in total. I almost passed out and about to call 911. I asked the crew to be honest and open the door. The lady next to me was lay down in the floor due to heat and no air inside the plane. I got headaches, can’t wait the replacement flight about midnight Dallas time. I end it up rebook for next day flight and stay overnight using my own pocket in a hotel nearby due to headaches and can’t breath. I still have a headache this morning. Still not decided yes how to file this issue to AA and/or FAA.

The Charleston, WV airport was cute. Very good staff and small enough to feel comfortable. The plane had more leg room than bigger planes. Much more comfortable.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports