HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$109+ 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
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Charleston to Caribbean Islands 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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 14, 2025.

Round-trip from

$348
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$509
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. 13% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:00 amCRW - SJU
2 stops17h 59mAmerican Airlines
Wed 10/224:45 pmSJU - CRW
1 stop6h 23mAmerican Airlines
Deal found 8/12$270
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/14:03 pmCRW - MBJ
1 stop23h 47mAmerican Airlines
Fri 11/73:50 pmMBJ - CRW
1 stop18h 50mAmerican Airlines
Deal found 8/13$348
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sun 9/288:07 pmCRW - NAS
2 stops15h 03mAmerican Airlines
Sun 10/56:40 pmNAS - CRW
2 stops15h 49mAmerican Airlines
Deal found 8/14$381
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 10/118:05 pmCRW - MBJ
2 stops18h 25mAmerican Airlines
Sat 10/1812:22 pmMBJ - CRW
2 stops21h 07mAmerican Airlines
Deal found 8/14$397
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/278:05 pmCRW - MBJ
2 stops16h 55mAmerican Airlines
Sun 11/24:05 pmMBJ - CRW
2 stops19h 45mAmerican Airlines
Deal found 8/12$402
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:38 pmCRW - PUJ
1 stop21h 47mAmerican Airlines
Tue 9/303:25 pmPUJ - CRW
1 stop20h 44mAmerican Airlines
Deal found 8/13$415
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:39 amCRW - NAS
1 stop6h 26mAmerican Airlines
Sun 9/146:48 pmNAS - CRW
2 stops17h 21mAmerican Airlines
Deal found 8/12$428
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/188:07 pmCRW - PUJ
2 stops18h 27mAmerican Airlines
Mon 9/221:35 pmPUJ - CRW
2 stops22h 34mAmerican Airlines
Deal found 8/13$471
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/118:07 pmCRW - PLS
2 stops16h 23mAmerican Airlines
Tue 9/163:20 pmPLS - CRW
2 stops8h 39mAmerican Airlines
Deal found 8/14$474
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:00 amCRW - SJU
2 stops14h 32mAmerican Airlines
Mon 11/246:25 amSJU - CRW
2 stops16h 27mAmerican Airlines
Deal found 8/12$480
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:09 pmCRW - SJU
1 stop7h 23mAmerican Airlines
Tue 11/252:05 pmSJU - CRW
2 stops8h 47mAmerican Airlines
Deal found 8/12$510
This United Airlines deal was found by Cheapflights users on 8/13. 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 9/272:00 pmCRW - PUJ
1 stop25h 05mUnited Airlines
Sat 10/41:50 pmPUJ - CRW
1 stop23h 35mUnited Airlines
Deal found 8/13$535

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 August 14, 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

Wed 10/15

6:00 am-11:59 pm

2 stops17h 59m

San Juan Luis Munoz Marin Intl

Wed 10/22

4:45 pm-11:08 pm

1 stop6h 23m

$270

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Sat 11/1

4:03 pm-2:50 pm

1 stop23h 47m

Montego Bay Sangster Intl

Fri 11/7

3:50 pm-10:40 am

1 stop18h 50m

$348

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Sun 9/28

8:07 pm-11:10 am

2 stops15h 03m

Nassau Intl

Sun 10/5

6:40 pm-10:29 am

2 stops15h 49m

$381

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Thu 1/29

6:10 pm-10:15 am

1 stop16h 05m

Montego Bay Sangster Intl

Wed 2/4

11:50 am-9:36 pm

1 stop9h 46m

$393

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Sat 10/11

8:05 pm-1:30 pm

2 stops18h 25m

Montego Bay Sangster Intl

Sat 10/18

12:22 pm-10:29 am

2 stops21h 07m

$397

CharlestonProvidenciales

CRW - PLS

CRWPLS

Charleston Yeager

Tue 1/6

6:10 pm-10:10 am

1 stop16h 00m

Providenciales

Tue 1/13

3:40 pm-9:36 pm

1 stop5h 56m

$398

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Mon 10/27

8:05 pm-12:00 pm

2 stops16h 55m

Montego Bay Sangster Intl

Sun 11/2

4:05 pm-11:50 am

2 stops19h 45m

$402

CharlestonPunta Cana

CRW - PUJ

CRWPUJ

Charleston Yeager

Fri 9/26

5:38 pm-3:25 pm

1 stop21h 47m

Punta Cana

Tue 9/30

3:25 pm-12:09 pm

1 stop20h 44m

$415

CharlestonNassau

CRW - NAS

CRWNAS

Charleston Yeager

Thu 9/11

6:39 am-1:05 pm

1 stop6h 26m

Nassau Intl

Sun 9/14

6:48 pm-12:09 pm

2 stops17h 21m

$428

CharlestonPunta Cana

CRW - PUJ

CRWPUJ

Charleston Yeager

Thu 9/18

8:07 pm-11:59 am

1 stop15h 52m

Punta Cana

Mon 9/22

1:35 pm-12:09 pm

2 stops22h 34m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 18 results
1
2

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 $254). Flying from Charleston, West Virginia to Caribbean Islands in June is currently the most expensive (average of $339). 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 August 14, 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
10,000 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Comfort

7.2

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Comfort

7.2

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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.

  • 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 - Nassau 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, September is the cheapest month in which you can book a flight from Charleston, West Virginia to Caribbean Islands (average of $254). Flying from Charleston, West Virginia to Caribbean Islands in June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Charleston to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Dallas/Fort Worth flights
Dulles Intl to Cancún flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Miami flights
Dulles Intl to Los Angeles flights
Dulles Intl to Las Vegas flights
Dulles Intl to San Francisco flights
Dulles Intl to Atlanta flights
Dulles Intl to Seattle flights
Dulles Intl to Orlando flights
Dulles Intl to Minneapolis flights
Dulles Intl to Midway flights
Dulles Intl to Boston flights
Dulles Intl to Mexico City flights
Dulles Intl to Denver flights
Dulles Intl to New Orleans flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to Tampa flights
Dulles Intl to Detroit flights
Dulles Intl to Austin flights
Pittsburgh to LaGuardia flights
Dulles Intl to Honolulu flights
Dulles Intl to Hobby flights
Dulles Intl to San Diego flights
Dulles Intl to Pearson Intl flights
Dulles Intl to George Bush Intcntl flights
Dulles Intl to Sky Harbor Intl flights
Dulles Intl to Charleston flights
Dulles Intl to Portland flights
Dulles Intl to Love Field flights
Dulles Intl to Providence flights
Pittsburgh to Boston flights
Dulles Intl to Salt Lake City flights
Dulles Intl to Fort Myers flights
Dulles Intl to Nashville flights
Dulles Intl to John F Kennedy Intl flights
Dulles Intl to Portland flights
Pittsburgh to Minneapolis flights
Pittsburgh to Orlando flights
Dulles Intl to Ontario flights
Pittsburgh to John F Kennedy Intl flights
Dulles Intl to Charlotte flights
Dulles Intl to Vancouver Intl flights
Dulles Intl to Jacksonville flights
Dulles Intl to LaGuardia flights
Pittsburgh to Las Vegas flights
Pittsburgh to Hobby flights
Dulles Intl to West Palm Beach flights
Pittsburgh to Dallas/Fort Worth flights
Pittsburgh to Fort Lauderdale flights

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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$301Average$485FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$370Average$627FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.