HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$121+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — SJU
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
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

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 February 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/228:52 pm
CRW
-
SJU
1 stop13h 18m
Multiple Airlines
Wed 3/258:47 pm
SJU
-
CRW
1 stop23h 25m
Multiple Airlines
Deal found 2/12$273
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Tue 11/38:06 am
CRW
-
SJU
1 stop6h 48m
American Airlines
Sat 11/146:44 am
SJU
-
CRW
2 stops16h 08m
American Airlines
Deal found 2/11$304
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Wed 3/115:00 am
CRW
-
MBJ
1 stop9h 26m
American Airlines
Mon 3/1612:28 pm
MBJ
-
CRW
1 stop21h 47m
American Airlines
Deal found 2/11$313
This American Airlines deal was found by Cheapflights users on 2/12. 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 6/18:05 pm
CRW
-
MBJ
2 stops18h 55m
American Airlines
Sat 6/62:44 pm
MBJ
-
CRW
2 stops18h 48m
American Airlines
Deal found 2/12$317
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Tue 4/76:00 am
CRW
-
SJU
2 stops16h 05m
American Airlines
Tue 4/145:45 am
SJU
-
CRW
2 stops15h 45m
American Airlines
Deal found 2/12$320
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Tue 10/138:16 pm
CRW
-
MBJ
2 stops16h 39m
American Airlines
Sun 10/182:27 pm
MBJ
-
CRW
2 stops18h 57m
American Airlines
Deal found 2/11$322
This American Airlines deal was found by Cheapflights users on 2/11. 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 3/26:08 pm
CRW
-
MBJ
1 stop20h 10m
American Airlines
Fri 3/61:22 pm
MBJ
-
CRW
1 stop21h 33m
American Airlines
Deal found 2/11$328
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Sun 6/216:54 am
CRW
-
MBJ
1 stop7h 37m
American Airlines
Fri 6/2612:30 pm
MBJ
-
CRW
1 stop10h 26m
American Airlines
Deal found 2/11$332
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sat 5/96:11 pm
CRW
-
PUJ
1 stop16h 34m
American Airlines
Wed 5/1311:51 am
PUJ
-
CRW
2 stops22h 43m
American Airlines
Deal found 2/12$333
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Sat 6/2011:02 am
CRW
-
MBJ
1 stop27h 29m
American Airlines
Thu 6/2512:30 pm
MBJ
-
CRW
1 stop10h 26m
American Airlines
Deal found 2/11$333
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Fri 6/198:05 pm
CRW
-
MBJ
1 stop18h 27m
American Airlines
Wed 6/2412:30 pm
MBJ
-
CRW
1 stop21h 02m
American Airlines
Deal found 2/11$334
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Sat 7/116:35 am
CRW
-
MBJ
1 stop5h 20m
American Airlines
Wed 7/155:17 pm
MBJ
-
CRW
2 stops16h 12m
American Airlines
Deal found 2/11$337

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 February 13, 2026.

Round-trip from

$273
(Kiwi.com)

One-way from

$121
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$785
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. 10% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 13, 2026.
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

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Sat 7/18

7:59 pm-10:55 am

1 stop15h 56m

Montego Bay Sangster Intl

Sat 7/25

5:17 pm-10:29 am

2 stops16h 12m

$317

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Mon 6/1

8:05 pm-1:28 pm

2 stops18h 23m

Montego Bay Sangster Intl

Fri 6/5

2:28 pm-10:32 am

2 stops19h 04m

$317

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Thu 6/18

8:05 pm-2:00 pm

2 stops18h 55m

Montego Bay Sangster Intl

Mon 6/22

2:23 pm-10:32 am

2 stops19h 09m

$317

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Sun 7/12

7:59 pm-3:20 pm

1 stop20h 21m

Montego Bay Sangster Intl

Fri 7/17

5:17 pm-10:29 am

2 stops16h 12m

$317

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Tue 4/7

6:00 am-10:05 pm

2 stops16h 05m

San Juan Luis Munoz Marin Intl

Tue 4/14

5:45 am-9:30 pm

2 stops15h 45m

$320

CharlestonPunta Cana

CRW - PUJ

CRWPUJ

Charleston Yeager

Sat 5/9

6:11 pm-2:34 pm

2 stops20h 23m

Punta Cana

Wed 5/13

2:30 pm-10:34 am

2 stops20h 04m

$333

CharlestonMontego Bay

CRW - MBJ

CRWMBJ

Charleston Yeager

Thu 6/11

8:05 pm-11:19 am

1 stop16h 14m

Montego Bay Sangster Intl

Wed 6/17

4:20 pm-10:32 am

1 stop17h 12m

$333

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Thu 3/5

8:52 pm-2:25 pm

1 stop16h 33m

San Juan Luis Munoz Marin Intl

Sun 3/8

5:30 am-8:12 pm

1 stop14h 42m

$362

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Wed 5/6

6:00 am-6:10 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Sun 5/10

4:30 pm-11:59 pm

1 stop7h 29m

$367

CharlestonSan Juan

CRW - SJU

CRWSJU

Charleston Yeager

Mon 2/23

8:04 pm-2:25 pm

1 stop17h 21m

San Juan Luis Munoz Marin Intl

Sat 2/28

8:05 pm-9:19 am

1 stop14h 14m

$373

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 43 results
1
2
3
...
5

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 February 13, 2026.
Read through reviews of airlines operating flights from Charleston to Caribbean Islands, such as Delta and 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.
Delta
7.9
Good
8,191 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,191 reviews
Delta
7.9
Good
8,191 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,277 reviews
Delta
7.9
Good
8,191 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 $313, American Airlines can have you in Caribbean Islands from Charleston, West Virginia in 9h 26m. The distance from Charleston, West Virginia to Caribbean Islands is about 1390 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 - 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

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 Miami flights
Dulles Intl to Orlando flights
Dulles Intl to Las Vegas flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to Cancún flights
Dulles Intl to Dallas/Fort Worth flights
Dulles Intl to Tampa flights
Dulles Intl to Hobby flights
Dulles Intl to Seattle flights
Dulles Intl to Los Angeles flights
Dulles Intl to Atlanta flights
Dulles Intl to Sky Harbor Intl flights
Dulles Intl to George Bush Intcntl flights
Dulles Intl to New Orleans flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Mexico City flights
Dulles Intl to San Francisco flights
Dulles Intl to Denver flights
Dulles Intl to Austin flights
Dulles Intl to Salt Lake City flights
Pittsburgh to Orlando flights
Dulles Intl to San Diego flights
Dulles Intl to West Palm Beach flights
Pittsburgh to Fort Lauderdale flights
Dulles Intl to Nashville flights
Pittsburgh to Las Vegas flights
Dulles Intl to Fort Myers flights
Pittsburgh to Tampa flights
Dulles Intl to Midway flights
Dulles Intl to Boston flights
Dulles Intl to Charlotte flights
Dulles Intl to Cozumel flights
Dulles Intl to Ontario flights
Pittsburgh to Miami flights
Pittsburgh to Newark flights
Dulles Intl to Honolulu flights
Pittsburgh to LaGuardia flights
Pittsburgh to John F Kennedy Intl flights
Dulles Intl to Jacksonville flights
Dulles Intl to Sarasota flights
Dulles Intl to Charleston flights
Dulles Intl to Love Field flights
Dulles Intl to San Antonio flights
Dulles Intl to Detroit flights
Pittsburgh to Denver flights
Dulles Intl to Minneapolis flights
Dulles Intl to Vancouver Intl flights
Dulles Intl to Portland flights
Pittsburgh to Boston flights
Dulles Intl to St. Louis 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 February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$307Average$643FlexibilityNo cancel feeOn-time71%
DeltaCheapest$325Average$501FlexibilityNo cancel feeOn-timeN/A

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.