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Caribbean Islands

$111+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — SJU
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Cheap 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 October 20, 2025.

Round-trip from

$275
(Delta)

One-way from

$111
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$291
From Charleston Yeager to Caribbean Islands
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One-way flight from Charleston Yeager to Caribbean Islands
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Highest demand for flights based on searches. 13% potential increase in price ($90 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($42 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 20, 2025.

This Delta deal was found by Cheapflights users on 10/20. 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.
Sun 12/73:49 pmCRW - SJU
1 stop6h 31mDelta
Fri 12/191:55 pmSJU - CRW
1 stop9h 54mDelta
Deal found 10/20$275
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 12/33:56 pmCRW - PUJ
2 stops18h 59mAmerican Airlines
Wed 12/105:30 pmPUJ - CRW
2 stops20h 07mAmerican Airlines
Deal found 10/19$306
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Wed 12/315:59 pmCRW - MBJ
1 stop16h 22mAmerican Airlines
Tue 1/1311:32 amMBJ - CRW
2 stops24h 22mAmerican Airlines
Deal found 10/20$366
This American Airlines deal was found by Cheapflights users on 10/17. 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.
Tue 12/27:46 amCRW - MBJ
1 stop7h 04mAmerican Airlines
Tue 12/93:48 pmMBJ - CRW
1 stop7h 06mAmerican Airlines
Deal found 10/17$410
This American Airlines deal was found by Cheapflights users on 10/17. 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.
Tue 12/305:59 pmCRW - MBJ
1 stop16h 22mAmerican Airlines
Tue 1/1311:32 amMBJ - CRW
2 stops24h 22mAmerican Airlines
Deal found 10/17$415
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 12/316:00 amCRW - MBJ
1 stop8h 13mDelta
Tue 1/138:00 amMBJ - CRW
1 stop8h 37mDelta
Deal found 10/19$424
This American Airlines deal was found by Cheapflights users on 10/19. 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 10/2710:59 amCRW - MBJ
1 stop5h 23mAmerican Airlines
Sun 11/21:40 pmMBJ - CRW
2 stops22h 10mAmerican Airlines
Deal found 10/19$431
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Sun 12/79:58 amCRW - SJU
2 stops33h 54mMultiple Airlines
Fri 12/1910:08 amSJU - CRW
1 stop9h 48mMultiple Airlines
Deal found 10/19$433
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/36:00 amCRW - SJU
2 stops16h 58mAmerican Airlines
Thu 11/62:05 pmSJU - CRW
1 stop9h 46mAmerican Airlines
Deal found 10/20$435
This United Airlines deal was found by Cheapflights users on 10/19. 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 10/275:45 pmCRW - MBJ
1 stop20h 01mUnited Airlines
Sun 11/22:48 pmMBJ - CRW
1 stop22h 35mUnited Airlines
Deal found 10/19$450
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/76:00 amCRW - SJU
2 stops15h 05mAmerican Airlines
Fri 12/198:25 amSJU - CRW
1 stop10h 04mAmerican Airlines
Deal found 10/20$516
This American Airlines deal was found by Cheapflights users on 10/19. 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 10/246:00 amCRW - SJU
2 stops16h 10mAmerican Airlines
Mon 10/277:05 amSJU - CRW
2 stops14h 29mAmerican Airlines
Deal found 10/19$536

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 October 20, 2025.
Use the filters below to find and compare flights from Charleston to Caribbean Islands that are best for you.

Fly from

Charleston

Fly to

Caribbean Islands

Route

Depart

Return

Price

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Tue 3/3

3:25 pm-11:49 pm

1 stop7h 24m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:15 am-2:42 pm

1 stop9h 27m

$275

CharlestonPunta Cana

CRW - PUJ

CRWPUJ

Charleston Yeager

Wed 12/3

3:56 pm-11:55 am

2 stops18h 59m

Punta Cana

Wed 12/10

5:30 pm-12:37 pm

2 stops20h 07m

$306

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Tue 3/10

7:00 am-8:26 pm

2 stops13h 26m

San Juan Luis Munoz Marin Intl

Wed 3/11

7:10 am-8:37 pm

2 stops13h 27m

$320

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Tue 12/30

5:59 pm-2:50 pm

2 stops20h 51m

Montego Bay Sangster Intl

Tue 1/13

11:32 am-11:54 am

2 stops24h 22m

$366

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Wed 12/31

5:59 pm-1:23 pm

2 stops19h 24m

Montego Bay Sangster Intl

Tue 1/13

11:32 am-11:54 am

2 stops24h 22m

$366

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Tue 12/2

6:00 am-2:50 pm

2 stops8h 50m

Montego Bay Sangster Intl

Tue 12/9

11:13 am-10:54 pm

2 stops11h 41m

$366

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Wed 12/31

5:59 pm-10:21 am

1 stop16h 22m

Montego Bay Sangster Intl

Thu 1/15

2:19 pm-11:54 am

2 stops21h 35m

$366

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Sun 12/7

3:49 pm-11:20 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Fri 12/19

1:55 pm-10:49 pm

1 stop9h 54m

$371

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Tue 3/3

5:39 am-11:30 pm

2 stops16h 51m

San Juan Luis Munoz Marin Intl

Thu 3/5

9:30 am-9:38 pm

1 stop13h 08m

$403

CharlestonSantiago de los Caballeros

CRW - STI

CRWSTI

Charleston Yeager

Mon 3/30

12:23 pm-12:15 pm

2 stops23h 52m

Santiago de los Caballeros

Thu 4/2

7:00 am-10:22 am

2 stops27h 22m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 29 results
1
2
3

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, September is the cheapest month in which you can book a flight from Charleston, West Virginia to Caribbean Islands (average of $206). Flying from Charleston, West Virginia to Caribbean Islands in August is currently the most expensive (average of $445). 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 October 20, 2025.
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
7.2
Good
11,024 reviews

Boarding

7.5

Food

6.4

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,024 reviews
American Airlines
7.2
Good
11,024 reviews

Boarding

7.5

Food

6.4

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 $275, Delta can have you in Caribbean Islands from Charleston, West Virginia in 7h 24m. 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 - San Juan Luis Munoz Marin Intl, Charleston Yeager - Providenciales or Charleston Yeager - Montego Bay Sangster Intl 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, September is the cheapest month in which you can book a flight from Charleston, West Virginia to Caribbean Islands (average of $206). Flying from Charleston, West Virginia to Caribbean Islands in August is currently the most expensive (average of $445). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Charleston to Caribbean Islands

Discover the top 2 airlines 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$317Average$485FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$377Average$624FlexibilityNo cancel feeOn-time71%

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