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Caribbean Islands

$151+ Cheap flights from Charleston, WV (CRW) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — SJU
May 2 — May 91
Sat 5/2
Sat 5/9
1 adult, Economy
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Cheap flight deals from Charleston to Caribbean Islands

Cheapest flights from Charleston to Caribbean Islands
Explore the most affordable flight options available from Charleston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2026.

This United Airlines deal was found by Cheapflights users on 4/1. 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 4/2910:30 am
CRW
-
SJU
1 stop10h 04m
United Airlines
Tue 5/51:00 am
SJU
-
CRW
2 stops13h 46m
United Airlines
Deal found 4/1$296
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Sun 4/266:11 pm
CRW
-
SJU
1 stop16h 37m
American Airlines
Fri 5/15:45 am
SJU
-
CRW
2 stops16h 15m
American Airlines
Deal found 3/30$302
This American Airlines deal was found by Cheapflights users on 3/29. 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 4/166:00 am
CRW
-
SJU
2 stops14h 51m
American Airlines
Thu 4/2311:43 am
SJU
-
CRW
2 stops10h 17m
American Airlines
Deal found 3/29$347
This American Airlines deal was found by Cheapflights users on 3/31. 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 11/277:51 pm
CRW
-
MBJ
1 stop14h 17m
American Airlines
Fri 12/41:55 pm
MBJ
-
CRW
1 stop22h 42m
American Airlines
Deal found 3/31$353
This United Airlines deal was found by Cheapflights users on 4/1. 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 6/26:00 am
CRW
-
NAS
1 stop8h 57m
United Airlines
Tue 6/93:59 pm
NAS
-
CRW
1 stop17h 26m
United Airlines
Deal found 4/1$356
This American Airlines deal was found by Cheapflights users on 3/31. 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 6/188:05 pm
CRW
-
MBJ
2 stops18h 50m
American Airlines
Mon 6/225:17 pm
MBJ
-
CRW
2 stops16h 15m
American Airlines
Deal found 3/31$357
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/276:11 pm
CRW
-
MBJ
1 stop18h 13m
American Airlines
Mon 5/41:15 pm
MBJ
-
CRW
2 stops19h 56m
American Airlines
Deal found 3/31$358
This Faresmojo deal was found by Cheapflights users on 3/31. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:00 am
CRW
-
SJU
1 stop7h 31m
JetBlue
Sun 6/212:41 pm
SJU
-
CRW
1 stop8h 54m
JetBlue
Deal found 3/31$359
This United Airlines deal was found by Cheapflights users on 3/29. 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 4/287:39 pm
CRW
-
NAS
2 stops18h 08m
United Airlines
Tue 5/512:35 pm
NAS
-
CRW
2 stops10h 14m
United Airlines
Deal found 3/29$360
This United Airlines deal was found by Cheapflights users on 4/2. 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 5/95:50 pm
CRW
-
PUJ
1 stop21h 22m
United Airlines
Fri 5/151:50 pm
PUJ
-
CRW
1 stop8h 59m
United Airlines
Deal found 4/2$363
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:52 pm
CRW
-
SJU
1 stop26h 37m
Multiple Airlines
Thu 5/77:00 am
SJU
-
CRW
2 stops26h 26m
Multiple Airlines
Deal found 4/1$365
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/136:11 pm
CRW
-
PUJ
1 stop16h 34m
American Airlines
Fri 4/1711:45 am
PUJ
-
CRW
1 stop22h 44m
American Airlines
Deal found 3/30$370

Find flight deals from Charleston to Caribbean Islands

Keep the following information in mind while searching for Charleston to Caribbean Islands flight deals. Data was last updated April 2, 2026.

Round-trip from

$296
(United Airlines)

One-way from

$151
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$454
From Charleston Yeager to Caribbean Islands
Search Deals
One-way flight from Charleston Yeager to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston to Caribbean Islands 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 2,558,603 searches. Data last updated April 2, 2026.
Use the filters below to find and compare flights from Charleston to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Wed 4/29

10:30 am-9:24 pm

2 stops10h 54m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-2:46 pm

2 stops13h 46m

$296

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Tue 6/2

6:00 am-2:57 pm

1 stop8h 57m

Nassau Intl

Tue 6/9

3:59 pm-9:25 am

1 stop17h 26m

$356

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Thu 6/18

8:05 pm-1:08 pm

2 stops18h 03m

Montego Bay Sangster Intl

Mon 6/22

2:08 pm-10:32 am

2 stops19h 24m

$357

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Sun 6/7

6:00 am-1:31 pm

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Sun 6/21

2:41 pm-11:35 pm

1 stop8h 54m

$359

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Tue 4/28

7:39 pm-1:47 pm

2 stops18h 08m

Nassau Intl

Tue 5/5

12:35 pm-10:49 pm

2 stops10h 14m

$360

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Wed 4/29

3:22 pm-11:13 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Wed 5/6

6:15 am-2:42 pm

1 stop8h 27m

$372

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Tue 4/14

6:45 am-2:44 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:20 am-10:49 pm

2 stops15h 29m

$372

CharlestonPunta Cana

CRW - PUJ

CRWPUJ

Charleston Yeager

Fri 5/8

6:11 pm-2:34 pm

2 stops20h 23m

Punta Cana

Tue 5/12

5:25 pm-10:34 am

2 stops17h 09m

$373

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Thu 5/14

6:45 am-2:57 pm

1 stop8h 12m

Nassau Intl

Thu 5/21

3:59 pm-9:25 am

1 stop17h 26m

$377
Quickest round-trip

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Tue 4/28

6:00 am-2:03 pm

1 stop8h 03m

Nassau Intl

Tue 5/5

5:58 pm-10:56 pm

1 stop4h 58m

$386

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 36 resultsSorted by cheapest first
1
2
3
4

Best time to book a flight from Charleston to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Charleston with our price prediction graph.
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 Islands

What is the cheapest month to book a flight from Charleston, West Virginia to Caribbean Islands?

Currently, December is the cheapest month in which you can book a flight from Charleston, West Virginia to Caribbean Islands (average of $170). Flying from Charleston, West Virginia to Caribbean Islands in November is currently the most expensive (average of $434). 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 2, 2026.
Read through reviews of airlines operating flights from Charleston to Caribbean Islands, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,550 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,550 reviews
American Airlines
7.1
Good
11,550 reviews

Boarding

7.5

Comfort

7.2

Food

6.4

Entertainment

6.9

Crew

8.0

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

Related info for your journey

Find useful and relevant information for your journey from Charleston to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Charleston to Caribbean Islands?

    Charleston Yeager (CRW), located 2.7 mi from the city center, is the airport you fly out of when you book flights from Charleston to Caribbean Islands.

  • How long is the flight from Charleston, West Virginia to Caribbean Islands?

    For as low as $359, United Airlines can have you in Caribbean Islands from Charleston, West Virginia in 7h 31m. The distance from Charleston, West Virginia to Caribbean Islands is about 1665 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Charleston, West Virginia to Caribbean Islands?

    When deciding which route to take from Charleston, West Virginia to Caribbean Islands consider Charleston Yeager - Montego Bay Sangster Intl, Charleston Yeager - San Juan Luis Munoz Marin Intl or Charleston Yeager - Punta Cana as they are the most popular.

  • Can I find deals for flights from Charleston to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Charleston to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Charleston to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Charleston to Caribbean Islands.

  • Can I find deals for business class flights from Charleston to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Charleston to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Charleston, West Virginia to Caribbean Islands?

    Currently, December is the cheapest month in which you can book a flight from Charleston, West Virginia to Caribbean Islands (average of $170). Flying from Charleston, West Virginia to Caribbean Islands in November is currently the most expensive (average of $434). 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.

See more FAQs

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Top airline flying from Charleston to Caribbean Islands

Discover the top airline that operate flights from Charleston to Caribbean Islands. 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 2,558,603 searches. Data last updated April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$307Average$606FlexibilityNo cancel feeOn-time71%

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