$111 Find Cheap Flights from Caribbean Islands to Charleston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Charleston departing on 2/20. 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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Everything you should know

Cheapest round-trip
$228
Typical prices: $283-$628
American Airlines
Thu 2/19Mon 2/23
SJU - CHS • 1 stop
Cheapest one-way
$171
Typical prices: $278-$363
Multiple Airlines
Fri 2/20
SJU - CHS • 2 stops
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean Islands to Charleston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Charleston 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 Caribbean Islands to Charleston

Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
5:18 pm - 11:51 pm
SJU
-
CHS
7h 33m
1 stop
American Airlines Logo
5:10 am - 11:40 am
CHS
-
SJU
5h 30m
1 stop
$228American Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
7:04 pm - 9:53 pm
SJU
-
CHS
27h 49m
1 stop
Multiple Airlines Logo
6:35 pm - 3:06 pm
CHS
-
SJU
19h 31m
2 stops
$257Multiple Airlines
Tue, Feb 17 - Wed, Feb 25
United Airlines Logo
2:05 am - 8:59 am
SJU
-
CHS
7h 54m
1 stop
United Airlines Logo
10:20 am - 9:00 pm
CHS
-
SJU
9h 40m
1 stop
$266United Airlines
Mon, Mar 9 - Tue, Mar 10
United Airlines Logo
1:05 am - 9:15 am
SJU
-
CHS
8h 10m
1 stop
United Airlines Logo
2:48 pm - 9:22 pm
CHS
-
SJU
6h 34m
1 stop
$271United Airlines
Sat, Mar 7 - Mon, Mar 16
Multiple Airlines Logo
10:12 pm - 1:04 pm
SJU
-
CHS
15h 52m
1 stop
Multiple Airlines Logo
12:05 pm - 8:30 pm
CHS
-
SJU
8h 25m
1 stop
$274Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
American Airlines Logo
4:40 pm - 11:59 pm
SJU
-
CHS
8h 19m
1 stop
American Airlines Logo
6:00 am - 11:34 pm
CHS
-
SJU
16h 34m
1 stop
$281American Airlines
Fri, Feb 6 - Fri, Feb 27
Delta Logo
7:31 am - 8:57 pm
SDQ
-
CHS
14h 26m
2 stops
Delta Logo
6:00 am - 7:14 pm
CHS
-
SDQ
12h 14m
1 stop
$321Delta
Wed, Feb 4 - Sat, Feb 7
Delta Logo
3:46 pm - 11:55 pm
SDQ
-
CHS
9h 09m
1 stop
Delta Logo
6:30 am - 2:21 pm
CHS
-
SDQ
6h 51m
1 stop
$326Delta
Tue, Mar 3 - Sat, Mar 7
JetBlue Logo
10:35 pm - 10:57 am
SDQ
-
CHS
13h 22m
1 stop
JetBlue Logo
12:36 pm - 1:58 am
CHS
-
SDQ
12h 22m
1 stop
$331JetBlue
Sat, Mar 7 - Sat, Mar 14
JetBlue Logo
11:06 pm - 9:58 am
STI
-
CHS
11h 52m
1 stop
JetBlue Logo
12:35 pm - 1:47 am
CHS
-
STI
13h 12m
1 stop
$339JetBlue
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$170
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from San Juan to Charleston

FAQs for booking flights from Caribbean Islands to Charleston

  • How does KAYAK find such low prices on flights from Caribbean Islands to Charleston?

    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 Caribbean Islands to Charleston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Charleston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Charleston from 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 Caribbean Islands to Charleston?

    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 to Charleston with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Charleston?

    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 to Charleston from 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 3 airlines serving from Caribbean Islands to Charleston

 
Need help choosing which airline to fly with from Caribbean Islands to Charleston? 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 8088 reviews
7.8Entertainment
8.1Boarding
7.2Food
7.9Comfort
8.5Crew
Airline reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

4.0 OkayJohn, Jan 2026
DAL - ATL
Read more Delta reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

My requested wheelchair never appeared. So many entertainment choices yet, I found little of interest and no internet option to search on my own. Both were minor issues.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

No enough space plus only allowing one laggage instead of two like other airlines.

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The comfort of Business Class made this trip far more comfortable. I was indeed surprised when I asked one of the flight attendant to help me set up my "bed", she responded that "We don't make beds in Business Class any longer...only First Class" I believe her name was Giselle, but I'm not certain. She did instruct me how to adjust the seat, place the hooded cover and I clearly understood how to place the blanket and the cover. Additionally, the meal I was served (a beef dish) was almost inedible. The beef was tough and odd tasting. I didn't mention it as I was hoping to quickly settle down and try to get some sleep.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

When I got to the waiting area, it was full but when the time came to board, rgete was no plane. The women where you would show your ticket, gave the news saying there was a maintenance problem and that it be an extra half hour wait. We never did see the plane but ultimately, Noone ever saw the plane because there was a fire on one engine. Needless to say, the wait time before it was announced what really happened, was a few hours. Many, many missed their plane transfer because they entered their first train. Also, the electronic info panels up on the different wall for all to see the status of each flight, never stated anything having to do with the long, long hold up. Many people had major problems because they had to swith planes during their trip and that never happened...

It was a good trip. Flight Attendants were friendly and responsive.

Extra legroom with my upgrade bundle. Clean aircraft, on-time departure, early arrival. Good value for the price.

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Even though the plane was delayed from the previous airport, the staff recognized this and kept us informed. The flight crew was absolutely awesome from on my flight from Ft. Meyers to AC. Great experience all around!

Flight was delayed would have liked it to have been on time. I didn't experience the food or entertainment but the boarding process was smooth and the flight crew worked well together and did a great job!

Not seat assigned because overbooking. We could go because some people decided to give their seats.

Spirit loves to pick and choose when to harass you about your personal item. I’ve flown numerous times with the same bag with no problem yet flying out of Orlando they forced me to pay $99 for a carry on and then ran out of overhead space. Do better!

For the price of the fare, there really isn’t much to complain about.

didn't order food on board. there's no way to hold a water botton on the way. otherwise it was a pleasant flight, thanks to the crew.

Even though there was a delay the crew was exceptional.

Even though there was a delay the crew was exeptional

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