$177+ Cheap flights from Charleston, WV (CRW) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — SJU
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Charleston to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Charleston to CaribbeanExplore the most affordable flight options available from Charleston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
Explore the most affordable flight options available from Charleston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:17 pm -
2 stops16h 03m
Tue 10/276:30 am -
2 stops12h 17m
Deal found 9/14![American Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:13 am -
1 stop11h 00m
Sun 12/206:30 am -
1 stop6h 19m
Deal found 9/15![Delta logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:59 pm -
1 stop15h 19m
Tue 10/203:12 pm -
1 stop7h 46m
Deal found 9/16![American Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:37 pm -
2 stops18h 20m
Thu 10/812:41 pm -
1 stop6h 48m
Deal found 9/14![American Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:08 pm -
2 stops19h 29m
Fri 12/184:37 pm -
2 stops25h 55m
Deal found 9/15![American Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:05 am -
2 stops11h 23m
Tue 12/812:56 pm -
2 stops12h 32m
Deal found 9/13![United Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop7h 25m
Tue 10/64:05 pm -
1 stop7h 25m
Deal found 9/14![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop8h 32m
Fri 10/22:08 pm -
2 stops20h 19m
Deal found 9/11![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop10h 49m
Tue 10/277:15 am -
1 stop6h 43m
Deal found 9/14![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop8h 32m
Thu 10/14:00 pm -
1 stop7h 20m
Deal found 9/11![Delta logo]()
$488
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:50 pm -
2 stops22h 23m
Tue 11/33:20 pm -
2 stops21h 55m
Deal found 9/11![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop8h 32m
Tue 10/64:05 pm -
1 stop7h 25m
Deal found 9/14![Delta logo]()
$502
Best flights from Charleston to CaribbeanDiscover carefully curated flight deals from Charleston to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Charleston to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/256:00 am -
1 stop6h 05m
Sun 1/316:15 am -
1 stop9h 26m
Deal found 9/14![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:59 pm -
1 stop15h 19m
Tue 10/203:12 pm -
1 stop7h 46m
Deal found 9/16![American Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:05 am -
2 stops11h 23m
Tue 12/812:56 pm -
2 stops12h 32m
Deal found 9/13![United Airlines logo]()
$426
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:59 pm -
1 stop15h 06m
Mon 11/211:51 am -
1 stop7h 36m
Deal found 9/11![American Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/213:25 pm -
1 stop7h 25m
Sun 1/246:15 am -
1 stop9h 26m
Deal found 9/15![Delta logo]()
$421
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:50 pm -
2 stops22h 23m
Tue 11/33:20 pm -
2 stops21h 55m
Deal found 9/11![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop7h 25m
Thu 10/14:00 pm -
1 stop7h 20m
Deal found 9/11![Delta logo]()
$488
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:05 pm -
2 stops22h 23m
Wed 10/285:35 pm -
2 stops19h 40m
Deal found 9/15![United Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop8h 32m
Tue 10/64:05 pm -
1 stop7h 25m
Deal found 9/14![Delta logo]()
$502
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2010:35 am -
1 stop9h 25m
Sat 1/307:40 am -
2 stops14h 29m
Deal found 9/14![United Airlines logo]()
$521
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:05 pm -
2 stops19h 28m
Tue 10/62:35 pm -
2 stops19h 08m
Deal found 9/11![United Airlines logo]()
$577
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop7h 25m
Mon 10/54:00 pm -
1 stop7h 20m
Deal found 9/14![Delta logo]()
$581
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:54 pm -
1 stop23h 38m
Wed 12/26:09 pm -
2 stops16h 14m
Deal found 9/15![American Airlines logo]()
$739
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/211:50 pm -
2 stops24h 24m
Wed 12/21:25 pm -
2 stops35h 03m
Deal found 9/13![United Airlines logo]()
$590
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:05 pm -
1 stop20h 55m
Sat 10/32:20 pm -
2 stops19h 23m
Deal found 9/11![United Airlines logo]()
$601
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:12 am -
1 stop8h 36m
Sat 1/235:21 pm -
2 stops27h 48m
Deal found 9/15![United Airlines logo]()
$627
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:50 pm -
2 stops23h 30m
Thu 10/295:06 pm -
2 stops44h 07m
Deal found 9/15![United Airlines logo]()
$633
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:05 pm -
2 stops28h 47m
Wed 10/76:00 am -
2 stops27h 43m
Deal found 9/12![United Airlines logo]()
$637
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/215:12 am -
2 stops15h 12m
Sat 1/232:05 am -
2 stops20h 04m
Deal found 9/15![United Airlines logo]()
$643
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/810:35 am -
1 stop27h 13m
Fri 2/123:20 pm -
2 stops29h 29m
Deal found 9/15![United Airlines logo]()
$689
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:50 pm -
2 stops26h 10m
Mon 11/95:06 pm -
2 stops20h 09m
Deal found 9/15![United Airlines logo]()
$701
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2210:35 am -
1 stop26h 43m
Sat 1/307:40 am -
2 stops14h 29m
Deal found 9/14![United Airlines logo]()
$746
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:29 am -
2 stops13h 21m
Fri 10/23:56 pm -
1 stop17h 35m
Deal found 9/13![United Airlines logo]()
$752
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:05 am -
2 stops32h 12m
Thu 12/105:06 pm -
2 stops31h 22m
Deal found 9/13![United Airlines logo]()
$845
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:05 am -
2 stops15h 19m
Sun 12/2010:15 am -
2 stops14h 46m
Deal found 9/11![United Airlines logo]()
$856
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:05 pm -
2 stops19h 40m
Thu 10/84:55 pm -
2 stops16h 48m
Deal found 9/11![United Airlines logo]()
$868
Last-minute flights from Charleston to CaribbeanDiscover last-minute flight deals from Charleston to Caribbean. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Charleston to Caribbean. Data last updated September 16, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:54 pm -
1 stop16h 48m
Fri 10/22:08 pm -
2 stops25h 44m
Deal found 9/15![Delta logo]()
$508
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:00 am -
1 stop7h 27m
Fri 10/21:50 pm -
2 stops19h 41m
Deal found 9/12![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop7h 25m
Tue 10/64:05 pm -
1 stop7h 25m
Deal found 9/14![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop8h 32m
Fri 10/22:08 pm -
2 stops20h 19m
Deal found 9/11![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop8h 32m
Thu 10/14:00 pm -
1 stop7h 20m
Deal found 9/11![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop8h 32m
Tue 10/64:05 pm -
1 stop7h 25m
Deal found 9/14![Delta logo]()
$502
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:37 pm -
2 stops18h 20m
Thu 10/812:41 pm -
1 stop6h 48m
Deal found 9/14![American Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:59 pm -
1 stop15h 19m
Tue 10/203:12 pm -
1 stop7h 46m
Deal found 9/16![American Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:17 pm -
2 stops16h 03m
Tue 10/276:30 am -
2 stops12h 17m
Deal found 9/14![American Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop10h 49m
Tue 10/277:15 am -
1 stop6h 43m
Deal found 9/14![Delta logo]()
$474
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:05 pm -
2 stops22h 23m
Wed 10/285:35 pm -
2 stops19h 40m
Deal found 9/15![United Airlines logo]()
$520
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:50 pm -
2 stops22h 23m
Tue 11/33:20 pm -
2 stops21h 55m
Deal found 9/11![United Airlines logo]()
$489
One-way flights from Charleston to CaribbeanSearch for one-way flight options from Charleston to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Charleston to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1611:20 am -
2 stops12h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$177
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:08 pm -
3 stops20h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$1,391
Find flight deals from Charleston to Caribbean
Keep the following information in mind while searching for Charleston to Caribbean flight deals. Data was last updated September 16, 2026.
Round-trip from | $316 (Delta) |
|---|---|
One-way from | $177 (Delta) |
Cheapflights Fare Finder
Customize your flight search to find flights from Charleston to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 16, 2026.
Use the filters below to find and compare flights from Charleston to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
CharlestonSantiago de los Caballeros
CRW Charleston Yeager - STI Santiago de los Caballeros
CRWSTI
Charleston Yeager
Mon 11/16
11:20 am-12:59 am
2 stops12h 39m
Santiago de los Caballeros
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$177
CharlestonSan Juan
CRW Charleston Yeager - SJU San Juan Luis Munoz Marin Intl
CRWSJU
Charleston Yeager
Mon 1/25
6:00 am-1:05 pm
1 stop6h 05m
San Juan Luis Munoz Marin Intl
Sun 1/31
6:15 am-2:41 pm
1 stop9h 26m
$392
CharlestonNassau
CRW Charleston Yeager - NAS Nassau Intl
CRWNAS
Charleston Yeager
Fri 10/16
7:59 pm-11:18 am
1 stop15h 19m
Nassau Intl
Tue 10/20
3:12 pm-10:58 pm
1 stop7h 46m
$400
CharlestonNassau
CRW Charleston Yeager - NAS Nassau Intl
CRWNAS
Charleston Yeager
Mon 10/26
7:59 pm-11:05 am
1 stop15h 06m
Nassau Intl
Mon 11/2
11:51 am-7:27 pm
1 stop7h 36m
$408
CharlestonSan Juan
CRW Charleston Yeager - SJU San Juan Luis Munoz Marin Intl
CRWSJU
Charleston Yeager
Thu 1/21
3:25 pm-11:50 pm
1 stop7h 25m
San Juan Luis Munoz Marin Intl
Sun 1/24
6:15 am-2:41 pm
1 stop9h 26m
$421
CharlestonPunta Cana
CRW Charleston Yeager - PUJ Punta Cana
CRWPUJ
Charleston Yeager
Tue 12/1
5:05 am-5:28 pm
2 stops11h 23m
Punta Cana
Tue 12/8
12:56 pm-12:28 am
2 stops12h 32m
$426
CharlestonPunta Cana
CRW Charleston Yeager - PUJ Punta Cana
CRWPUJ
Charleston Yeager
Tue 9/29
6:00 am-1:25 pm
1 stop7h 25m
Punta Cana
Thu 10/1
4:00 pm-11:20 pm
1 stop7h 20m
$488
CharlestonMontego Bay
CRW Charleston Yeager - MBJ Montego Bay Sangster Intl
CRWMBJ
Charleston Yeager
Tue 10/27
1:50 pm-11:13 am
2 stops22h 23m
Montego Bay Sangster Intl
Tue 11/3
3:20 pm-1:15 pm
2 stops21h 55m
$489
CharlestonPunta Cana
CRW Charleston Yeager - PUJ Punta Cana
CRWPUJ
Charleston Yeager
Tue 9/29
6:00 am-2:32 pm
1 stop8h 32m
Punta Cana
Tue 10/6
4:05 pm-11:30 pm
1 stop7h 25m
$502
CharlestonPunta Cana
CRW Charleston Yeager - PUJ Punta Cana
CRWPUJ
Charleston Yeager
Sat 10/24
6:05 pm-4:28 pm
2 stops22h 23m
Punta Cana
Wed 10/28
5:35 pm-1:15 pm
2 stops19h 40m
$520
Showing 1-10 of 28 resultsSorted by cheapest first
Best time to book a flight from Charleston to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Charleston with our price prediction graph.
CRW-STI
CRW-SJU
CRW-NAS
CRW-PUJ
CRW-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Charleston to Caribbean
CRW-0CB
CRW-STI
CRW-SJU
CRW-NAS
CRW-PUJ
What is the cheapest month to book a flight from Charleston, West Virginia to Caribbean?
Currently, March is the cheapest month in which you can book a flight from Charleston, West Virginia to Caribbean (average of $346). Flying from Charleston, West Virginia to Caribbean in November is currently the most expensive (average of $1,610). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated September 16, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from Charleston to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
Find useful and relevant information for your journey from Charleston to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Charleston to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Charleston to Caribbean by cabin class
Find flights from Charleston to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Charleston and Caribbean flights
Browse other Charleston and Caribbean flight options. Last updated on September 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Charleston to Caribbean flights
Consider these flights traveling from Charleston to Caribbean.
Top airline flying from Charleston to Caribbean
Discover the top airline that operate flights from Charleston to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$312 | Average$731 | FlexibilityNo cancel fee | On-time71% |