$147 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 6/2. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Caribbean Islands, as well as popular online travel agencies
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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$370
Montego Bay
Montego Bay2 stops$357
Nassau
Nassau1 stop$376
Providenciales
Providenciales1 stop$586
Punta Cana
Punta Cana1 stop$370
Montego Bay
Montego Bay2 stops$357
Nassau
Nassau1 stop$376
Providenciales
Providenciales1 stop$586

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, May 9 - Fri, May 15
American Airlines Logo
7:42 am - 10:05 pm
CRW
-
SJU
14h 23m
2 stops
American Airlines Logo
5:45 am - 10:00 pm
SJU
-
CRW
16h 15m
2 stops
$272American Airlines
Sat, May 9 - Fri, May 15
American Airlines Logo
6:11 pm - 10:48 am
CRW
-
SJU
16h 37m
1 stop
American Airlines Logo
5:45 am - 10:00 pm
SJU
-
CRW
16h 15m
2 stops
$312American Airlines
Thu, Jun 18 - Mon, Jun 22
American Airlines Logo
8:05 pm - 1:55 pm
CRW
-
MBJ
18h 50m
2 stops
American Airlines Logo
2:30 pm - 10:32 am
MBJ
-
CRW
19h 02m
2 stops
$357American Airlines
Wed, Apr 29 - Wed, May 6
United Airlines Logo
7:39 pm - 3:12 pm
CRW
-
PUJ
19h 33m
1 stop
United Airlines Logo
1:50 pm - 10:49 pm
PUJ
-
CRW
8h 59m
1 stop
$370United Airlines
Mon, Apr 13 - Fri, Apr 17
American Airlines Logo
6:11 pm - 1:02 pm
CRW
-
PUJ
18h 51m
2 stops
American Airlines Logo
5:25 pm - 10:29 am
PUJ
-
CRW
17h 04m
2 stops
$373American Airlines
Wed, Apr 29 - Wed, May 6
United Airlines Logo
7:39 pm - 3:12 pm
CRW
-
PUJ
19h 33m
1 stop
United Airlines Logo
2:20 pm - 9:31 am
PUJ
-
CRW
19h 11m
2 stops
$374United Airlines
Tue, Apr 28 - Tue, May 5
American Airlines Logo
6:00 am - 11:07 am
CRW
-
NAS
5h 07m
1 stop
American Airlines Logo
11:57 am - 9:30 pm
NAS
-
CRW
9h 33m
1 stop
$376American Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
6:11 pm - 2:34 pm
CRW
-
PUJ
20h 23m
2 stops
American Airlines Logo
1:39 pm - 10:34 am
PUJ
-
CRW
20h 55m
2 stops
$378American Airlines
Wed, Jul 29 - Mon, Aug 3
Delta Logo
11:00 am - 3:54 pm
CRW
-
NAS
4h 54m
1 stop
Delta Logo
5:20 pm - 10:41 pm
NAS
-
CRW
5h 21m
1 stop
$416Delta
Mon, Jun 1 - Sun, Jun 14
JetBlue Logo
3:30 pm - 10:17 pm
CRW
-
SJU
6h 47m
1 stop
JetBlue Logo
2:40 pm - 10:41 pm
SJU
-
CRW
8h 01m
1 stop
$426JetBlue
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 $338, 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 October, when tickets cost $291 (return) on average. On the other hand, the most expensive months are July and February, when the average cost of round-trip tickets is $1,038 and $902 respectively.

Good to know

Low seasonOctober
Cheapest flight$147
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 13% lower on average.
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 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.
7.9
DeltaOverall score based on 8291 reviews
8.1Boarding
8.5Crew
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

No WiFi. Arrival was early but gate was occupied and had to sit on jet 30 min to deplane.

No WiFi on flight. Arrival was early but gate was occupied and had to sit on jet for nearly 30 min to deplane.

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Flight attendants were kind and courteous. We were a delayed due to the incoming flight; but we made it safe which is what matters. Thanks!

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports