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Caribbean Islands

$161+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — SJU
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
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 December 27, 2025.

This Delta deal was found by Cheapflights users on 12/27. 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 12/3112:25 pmCRW - MBJ
1 stop8h 16mDelta
Tue 1/132:19 pmMBJ - CRW
1 stop8h 20mDelta
Deal found 12/27$404
This American Airlines deal was found by Cheapflights users on 12/27. 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
2 stops19h 24mAmerican Airlines
Tue 1/134:16 pmMBJ - CRW
2 stops19h 38mAmerican Airlines
Deal found 12/27$442
This Delta deal was found by Cheapflights users on 12/25. 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.
Sat 12/2712:25 pmCRW - MBJ
1 stop8h 16mDelta
Wed 12/318:00 amMBJ - CRW
1 stop12h 53mDelta
Deal found 12/25$467
This American Airlines deal was found by Cheapflights users on 12/27. 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 12/277:11 amCRW - MBJ
1 stop7h 03mAmerican Airlines
Wed 12/311:25 pmMBJ - CRW
1 stop21h 16mAmerican Airlines
Deal found 12/27$632
This American Airlines deal was found by Cheapflights users on 12/26. 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 12/317:11 amCRW - SJU
1 stop13h 40mAmerican Airlines
Mon 1/56:15 pmSJU - CRW
1 stop7h 11mAmerican Airlines
Deal found 12/26$644
This American Airlines deal was found by Cheapflights users on 12/25. 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 12/265:59 pmCRW - NAS
2 stops17h 20mAmerican Airlines
Wed 12/311:12 pmNAS - CRW
1 stop4h 17mAmerican Airlines
Deal found 12/25$724
This United Airlines deal was found by Cheapflights users on 12/26. 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 12/261:57 pmCRW - SJU
2 stops31h 25mUnited Airlines
Mon 12/292:05 amSJU - CRW
2 stops12h 17mUnited Airlines
Deal found 12/26$898
This United Airlines deal was found by Cheapflights users on 12/27. 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 12/311:57 pmCRW - SJU
2 stops15h 14mUnited Airlines
Mon 1/55:50 pmSJU - CRW
2 stops24h 12mUnited Airlines
Deal found 12/27$1,087
This United Airlines deal was found by Cheapflights users on 12/25. 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 12/267:00 amCRW - SJU
1 stop13h 00mUnited Airlines
Fri 1/22:05 amSJU - CRW
2 stops12h 17mUnited Airlines
Deal found 12/25$1,107
This American Airlines deal was found by Cheapflights users on 12/26. 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 12/265:59 pmCRW - SJU
1 stop18h 55mAmerican Airlines
Tue 12/308:25 amSJU - CRW
1 stop17h 01mAmerican Airlines
Deal found 12/26$1,236

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 December 27, 2025.

Round-trip from

$271
(American Airlines)

One-way from

$161
(United Airlines)

Popular in

July

Cheapest in

October

Average price

$599
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. 18% potential increase in price ($126 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 27, 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

Mon 2/23

6:00 am-9:33 pm

2 stops14h 33m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:15 pm-10:40 am

1 stop17h 25m

$271

CharlestonPunta Cana

CRW - PUJ

CRWPUJ

Charleston Yeager

Sat 3/14

6:08 pm-11:02 am

2 stops16h 54m

Punta Cana

Wed 3/18

12:00 pm-10:55 am

2 stops22h 55m

$306

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Sat 2/7

6:00 am-11:19 am

1 stop5h 19m

Nassau Intl

Sat 2/14

12:04 pm-9:20 pm

1 stop9h 16m

$325

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Mon 2/9

5:49 am-1:20 pm

1 stop7h 31m

Nassau Intl

Mon 2/16

5:20 pm-11:13 am

1 stop17h 53m

$326

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Sat 2/28

5:35 pm-6:11 am

2 stops11h 36m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:40 am-8:38 pm

2 stops13h 58m

$331

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Sat 5/2

6:13 pm-2:15 pm

2 stops21h 02m

Montego Bay Sangster Intl

Sat 5/9

3:10 pm-10:29 am

2 stops18h 19m

$336

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Sat 2/28

11:12 am-9:33 pm

1 stop9h 21m

San Juan Luis Munoz Marin Intl

Wed 3/4

1:58 pm-11:24 pm

2 stops10h 26m

$353

CharlestonProvidenciales

CRW - PLS

CRWPLS

Charleston Yeager

Sun 1/25

5:37 pm-4:00 pm

2 stops22h 23m

Providenciales

Thu 1/29

5:06 pm-5:02 pm

2 stops23h 56m

$377

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Thu 2/19

6:00 am-9:33 pm

2 stops14h 33m

San Juan Luis Munoz Marin Intl

Thu 2/26

2:26 pm-11:24 pm

2 stops9h 58m

$393

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Sun 2/22

5:35 pm-6:11 am

2 stops11h 36m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:40 am-8:38 pm

2 stops13h 58m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 25 results
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2
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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 July is currently the most expensive (average of $832). 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 December 27, 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
11,067 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,067 reviews
American Airlines
7.2
Good
11,067 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 $271, American Airlines can have you in Caribbean Islands from Charleston, West Virginia in 14h 33m. 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 - Montego Bay Sangster Intl or Charleston Yeager - Nassau 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, 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 July is currently the most expensive (average of $832). 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.

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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 December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$301Average$485FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$381Average$639FlexibilityNo cancel feeOn-time71%

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