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$98+ Cheap flights from Charlottesville (CHO) to Caribbean

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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Feb 17 — Feb 241
Tue 2/17
Tue 2/24
1 adult, Economy
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Cheap flight deals from Charlottesville to Caribbean

Keep the following information in mind while searching for Charlottesville to Caribbean flight deals. Data was last updated January 18, 2026.

Round-trip from

$232
(American Airlines)

One-way from

$98
(United Airlines)

Popular in

August

Cheapest in

May

Average price

$765
From Charlottesville Albemarle to Caribbean
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One-way flight from Charlottesville Albemarle to Caribbean
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Highest demand for flights based on searches. 5% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Charlottesville to Caribbean

Cheapest flights from Charlottesville to Caribbean
Explore the most affordable flight options available from Charlottesville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 18, 2026.

This American Airlines deal was found by Cheapflights users on 1/16. 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 2/227:57 pm
CHO
-
SJU
1 stop16h 56m
American Airlines
Thu 2/265:18 pm
SJU
-
CHO
1 stop16h 09m
American Airlines
Deal found 1/16$232
This United Airlines deal was found by Cheapflights users on 1/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:29 pm
CHO
-
SXM
1 stop16h 21m
United Airlines
Mon 3/303:50 pm
SXM
-
CHO
2 stops18h 20m
United Airlines
Deal found 1/17$290
This United Airlines deal was found by Cheapflights users on 1/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:20 am
CHO
-
SXM
1 stop6h 30m
United Airlines
Tue 3/313:50 pm
SXM
-
CHO
1 stop18h 08m
United Airlines
Deal found 1/17$291
This American Airlines deal was found by Cheapflights users on 1/18. 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 3/97:57 pm
CHO
-
GCM
1 stop16h 13m
American Airlines
Thu 3/1211:40 am
GCM
-
CHO
2 stops19h 47m
American Airlines
Deal found 1/18$302
This American Airlines deal was found by Cheapflights users on 1/18. 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 3/47:17 pm
CHO
-
GCM
1 stop16h 51m
American Airlines
Wed 3/1112:05 pm
GCM
-
CHO
2 stops19h 22m
American Airlines
Deal found 1/18$308
This American Airlines deal was found by Cheapflights users on 1/17. 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 3/245:30 pm
CHO
-
SXM
2 stops21h 58m
American Airlines
Mon 3/302:17 pm
SXM
-
CHO
2 stops19h 30m
American Airlines
Deal found 1/17$316
This American Airlines deal was found by Cheapflights users on 1/17. 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.
Thu 2/55:20 pm
CHO
-
GCM
2 stops18h 45m
American Airlines
Mon 2/912:50 pm
GCM
-
CHO
2 stops21h 09m
American Airlines
Deal found 1/17$318
This American Airlines deal was found by Cheapflights users on 1/17. 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.
Sat 2/217:57 pm
CHO
-
PUJ
1 stop14h 37m
American Airlines
Tue 3/35:41 pm
PUJ
-
CHO
1 stop17h 06m
American Airlines
Deal found 1/17$319
This American Airlines deal was found by Cheapflights users on 1/16. 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 1/317:09 pm
CHO
-
SJU
1 stop16h 59m
American Airlines
Wed 2/46:00 am
SJU
-
CHO
2 stops11h 07m
American Airlines
Deal found 1/16$322
This American Airlines deal was found by Cheapflights users on 1/17. 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.
Sun 2/17:09 pm
CHO
-
PUJ
1 stop16h 46m
American Airlines
Fri 2/65:26 pm
PUJ
-
CHO
2 stops17h 33m
American Airlines
Deal found 1/17$323
This American Airlines deal was found by Cheapflights users on 1/16. 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 2/105:20 pm
CHO
-
NAS
2 stops17h 33m
American Airlines
Fri 2/206:04 pm
NAS
-
CHO
2 stops14h 23m
American Airlines
Deal found 1/16$328
This American Airlines deal was found by Cheapflights users on 1/16. 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 3/27:57 pm
CHO
-
NAS
2 stops15h 01m
American Airlines
Mon 3/912:48 pm
NAS
-
CHO
1 stop20h 59m
American Airlines
Deal found 1/16$333

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charlottesville to Caribbean 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 January 18, 2026.
Use the filters below to find and compare flights from Charlottesville to Caribbean that are best for you.

Fly from

Charlottesville

Fly to

Caribbean

Route

Depart

Return

Price

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sun 2/22

7:57 pm-1:53 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

Thu 2/26

5:18 pm-8:27 am

1 stop16h 09m

$232

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 3/24

6:20 am-12:50 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Mon 3/30

3:50 pm-10:10 am

2 stops18h 20m

$290

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 3/23

8:29 pm-12:50 pm

1 stop16h 21m

Simpson Bay Princess Juliana

Mon 3/30

3:50 pm-10:10 am

2 stops18h 20m

$290

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Wed 3/25

6:20 am-12:50 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Tue 3/31

3:50 pm-9:58 am

1 stop18h 08m

$291

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 3/24

6:20 am-12:50 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Tue 3/31

3:50 pm-9:58 am

1 stop18h 08m

$291

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 3/30

6:20 am-12:33 pm

1 stop6h 13m

Simpson Bay Princess Juliana

Tue 3/31

3:50 pm-1:53 pm

1 stop22h 03m

$291

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Mon 3/9

7:57 pm-11:10 am

1 stop16h 13m

George Town Owen Roberts Intl

Thu 3/12

11:40 am-8:27 am

2 stops19h 47m

$302

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Wed 3/4

5:30 pm-2:45 pm

2 stops21h 15m

George Town Owen Roberts Intl

Wed 3/11

12:05 pm-8:27 am

2 stops19h 22m

$302

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 3/24

5:30 pm-11:29 am

2 stops17h 59m

Simpson Bay Princess Juliana

Tue 3/31

4:28 pm-4:31 pm

2 stops24h 03m

$316

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Wed 3/25

7:57 pm-3:28 pm

2 stops19h 31m

Simpson Bay Princess Juliana

Tue 3/31

2:17 pm-8:27 am

2 stops18h 10m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/17

Showing 1-10 of 47 results
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Best time to book a flight from Charlottesville to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Charlottesville 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 Charlottesville to Caribbean

What is the cheapest month to book a flight from Charlottesville to Caribbean?

Currently, January is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $80). Flying from Charlottesville to Caribbean in December is currently the most expensive (average of $166). 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated January 18, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Charlottesville to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,176 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,176 reviews
United Airlines
7.4
Good
9,176 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,160 reviews
United Airlines
7.4
Good
9,176 reviews

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Charlottesville to Caribbean. 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 Charlottesville to Caribbean?

    Charlottesville Albemarle (CHO), located 7.6 mi from the city center, is the airport you fly out of when you book flights from Charlottesville to Caribbean.

  • How long is the flight from Charlottesville to Caribbean?

    For as low as $290, American Airlines can have you in Caribbean from Charlottesville in 6h 30m. The distance from Charlottesville to Caribbean is about 1668 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Charlottesville to Caribbean?

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

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

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

  • How can I find direct flights from Charlottesville to Caribbean?

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

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

    Yes. Cheapflights offers flight deals from Charlottesville to Caribbean 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 Charlottesville to Caribbean?

    Currently, January is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $80). Flying from Charlottesville to Caribbean in December is currently the most expensive (average of $166). 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

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Alternative routes for Charlottesville to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Charlottesville to Caribbean

Discover the top 2 airlines that operate flights from Charlottesville to Caribbean. 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 January 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$329Average$659FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$414Average$559FlexibilityNo cancel feeOn-time69%

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