
Cheap Flights from Charleston to Caribbean Islands
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysKAYAK'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?
No, with an average price for the route of $375, prices are generally cheapest when you fly direct.
What is the cheapest month to fly from Charleston to Caribbean Islands?
The cheapest month for flights from Charleston to Caribbean Islands is February, when tickets cost $529 (return) on average. On the other hand, the most expensive months are November and September, when the average cost of round-trip tickets is $681 and $672 respectively.
Good to know
Low season | September |
|---|---|
High season | June |
FAQs - booking Caribbean Islands flights
Reviews of the top 5 airlines serving from Charleston to Caribbean Islands
I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.
I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.
Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.
Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.
One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.
Despite paying for an ‘upgraded’ seat in row 1, I had to put my luggage in the middle of the plane. Snacks were bleh and seat was small and uncomfortable and I am not large. Attendants were fine but not super helpful. Plane just seemed outdated.
It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.
Delayed for no reason at all originally. Then they said it was due to weather conditions. Communication between kayak and Southwest was terrible because both displayed different delays and departure times for HOURS throughout the day. The plane then had technical issues which delayed us from taking off even longer. Didn’t actually take off until 11:45pm when the original departure time was 7:35pm. I didn’t get home until 1:30am the next day. I was exhausted and pissed off. I am not confident if I’ll fly southwest in the future or use kayak to book.
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.
Flight was very delayed so I was able to get on an earlier flight via stand-by. Crew communicated effectively around delay and worked to make customers comfortable. Wifi was ok, streaming TV was great. App functionality broke down once I was moved to stand-by on earlier flight.
Two of the flight attendants were cranky and seemed like they didn’t want to be there. Not up to normal Delta standards. And our bags didn’t make flight to Italy from Amsterdam resulting in having to make a trip back to airport which cost me 75 euros.
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.
Flight delayed over an hour with plane on runway because of weather in an area of the country we were not in or flying to.
Flight was delayed almost an hour because the cleaning crew broke one of the bathroom doors.
Comfortable seats and good crew. There should be some breakfast options in menu for economy class to purchase Wifi was not working in the flight
First class flight crew was barely available. They came through 3 times while we were on the plane for nearly 4 hours.
Please stop those idiotic and unrelenting announcements, commercials and stupid credit card drivel. All together about 15 minutes of stupidness that annoys each passenger.
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.
My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.
The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.
Terrible. We originally booked a direct flight from BOS to MCO on 9/28 at 8:00pm and it was cancelled due to unforeseen circumstances and the flight we were rebooked on was on 9/29 at 7:00am with a layover in JFK. We were traveling with sick kids so leaving at such an early hour was absolutely miserable, and on top of that we all missed work which we couldn’t afford. On top of that- we paid a fortune for our flights to be direct without a layover and the flights with layovers were cheaper so at the very minimum we should have been refunded the difference. With absolutely no explanation or sympathy from JetBlue- we will avoid using them in the future due to the fact they aren’t reliable nor do they correct their mistakes.
Experience with JetBlue was poor. We were originally suppose to fly home on a direct flight on Monday the 28th at 8:00pm and we it was canceled due to “unforeseen circumstances” and we were rebooked on a 7am flight on Tuesday the 29th with a layover in JFK. Traveling with sick kids and waking up at an ungodly hour was miserable, and not only that it caused all of us to miss work. We intentionally flew our Monday on a direct flight and the direct flight was far more than the non direct flights on any given day. There was no compensation provided let alone a reasonable explanation. When you are charging people those type of prices for domestic same coast flights- you should be at least refunding the cost difference of the flights if you are rebooking them on a cheaper flight. I will never fly JetBlue again because they are unreliable and don’t correct their mistakes.
Wasn’t very happy with our flight home due to the fact it was cancelled with absolutely no reason. It was a direct flight at 8:00pm on Monday and they rebooked us for a 7am flight on Tuesday with a layover. Traveling with sick kids, getting up that early was miserable and on top of that we all missed a day of work that we couldn’t afford to with absolutely no apology or compensation from JetBlue. The original cost of the flights were astronomical because we flew out on Monday over Tuesday and also we paid extra for the direct flight then we would have for the flight with a layover. Super disappointed Jetblue truly could have cared less. Will avoid them in the future due to the fact they aren’t reliable nor compassionate for the inconvenience these changes cost their clients.
No WiFi, no power to charge phone, confusing boarding, delays
There is a considerable amount of people that use the wheel chair pre boarding along of large groups of family / friends. This is not right should be limited only to the person in need and the airline assistant. Some of these people use overhead bins that do not belong to them. The aircraft had a non functional wifi . The service was bad.
Flight was delayed 3 hours. No food on plane besides snacks
Every thing went smooth. No complaints except deplaning could have been quicker
I was grossly overcharged to change my return flight. Had to do it through Kayak because it was booked that way and I was not given the fare price listed at the time on JetBlue or kayak. Was traveling with another couple that booked directly through JetBlue and they paid the $100 change fee and the difference between what they paid originally(same as me) and the displayed fares and it was less than $400 total for two tickets. I paid almost $700 to change the same fare tickets they purchased and had to pay again for upgraded seat selection that I previously paid for on top of the almost $700 increase. Difficult to talk to the kayak representative because of his accent. Told me I had to wait for confirmation to be sure it had been changed and that I could take up to a few hours. The call itself after the wait time took almost 30 minutes, which could’ve been done directly on JetBlue in 2 to 3 minutes.. My husband and I were given separate boarding zones. They would not let us board together. I had to board in the last zone. They made me check my bag even though my husband told me that he had a spot to put my carry-on. Since he boarded before me. The flight crew tried to accommodate, but the woman that was boarding in the terminal came down and would not let me take my carry-on. She was aggressive, rude and condescending to everybody in line and told them she was being audited. When I told her that my husband had secured a spot for me to put my carry-on with his backpack, that would then move to under the seat. She told me that she couldn’t play favorites, although I was second to last to board the plane since my boarding zone was changed. They told me because I forwarded my husband his ticket that’s what separated our boarding zones, but would not allow us to board together. The volume on my TV would not work, and my upgraded seat would not go into the fully upright position so I was told repeatedly during takeoff and landing to put my chair into the upright position which was embarrassing and uncomfortable to be told assertively so many times. I will not book through kayak again.
I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American
The first flight was delayed by an hour and a half, so we missed the second flight. They rebooked us on the later flight and I have to sit in the middle for more than 5 hours. Terrible experience. No more American Airlines.
Flight was fine, but not having WiFi was a major negative
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.