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Caribbean Islands

$110+ Cheap flights from Charlottesville (CHO) 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap flight deals from Charlottesville to Caribbean Islands

Cheapest flights from Charlottesville to Caribbean Islands
Explore the most affordable flight options available from Charlottesville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.

This American Airlines deal was found by Cheapflights users on 2/9. 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 4/77:13 pm
CHO
-
MBJ
2 stops17h 38m
American Airlines
Tue 4/1412:56 pm
MBJ
-
CHO
2 stops18h 43m
American Airlines
Deal found 2/9$317
This American Airlines deal was found by Cheapflights users on 2/9. 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 2/9$319
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 2/236:00 am
CHO
-
SJU
1 stop10h 27m
Delta
Thu 2/266:15 am
SJU
-
CHO
1 stop8h 31m
Delta
Deal found 2/9$322
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 3/106:00 am
CHO
-
SJU
1 stop10h 18m
Delta
Tue 3/171:00 pm
SJU
-
CHO
1 stop9h 48m
Delta
Deal found 2/8$329
This American Airlines deal was found by Cheapflights users on 2/10. 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 5/268:00 pm
CHO
-
NAS
1 stop14h 03m
American Airlines
Tue 6/22:18 pm
NAS
-
CHO
1 stop18h 15m
American Airlines
Deal found 2/10$343
This American Airlines deal was found by Cheapflights users on 2/10. 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 5/510:19 am
CHO
-
SJU
1 stop10h 32m
American Airlines
Sun 5/104:30 pm
SJU
-
CHO
1 stop7h 24m
American Airlines
Deal found 2/10$347
This United Airlines deal was found by Cheapflights users on 2/8. 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 3/1010:45 am
CHO
-
SJU
2 stops12h 51m
United Airlines
Tue 3/177:05 am
SJU
-
CHO
1 stop6h 54m
United Airlines
Deal found 2/8$349
This American Airlines deal was found by Cheapflights users on 2/9. 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 4/168:03 pm
CHO
-
SXM
2 stops19h 19m
American Airlines
Mon 4/2012:41 pm
SXM
-
CHO
2 stops21h 13m
American Airlines
Deal found 2/9$350
This United Airlines deal was found by Cheapflights users on 2/8. 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 2/236:20 am
CHO
-
SJU
1 stop5h 57m
United Airlines
Thu 2/262:05 am
SJU
-
CHO
2 stops15h 58m
United Airlines
Deal found 2/8$352
This United Airlines deal was found by Cheapflights users on 2/10. 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 5/275:45 pm
CHO
-
SJU
2 stops11h 44m
United Airlines
Tue 6/21:00 am
SJU
-
CHO
2 stops8h 26m
United Airlines
Deal found 2/10$359
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 2/236:00 am
CHO
-
SJU
1 stop10h 27m
Delta
Tue 3/37:30 am
SJU
-
CHO
1 stop7h 16m
Delta
Deal found 2/9$363
This American Airlines deal was found by Cheapflights users on 2/9. 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 5/127:13 pm
CHO
-
MBJ
1 stop15h 00m
American Airlines
Sat 5/1612:56 pm
MBJ
-
CHO
2 stops18h 43m
American Airlines
Deal found 2/9$373

Find flight deals from Charlottesville to Caribbean Islands

Keep the following information in mind while searching for Charlottesville to Caribbean Islands flight deals. Data was last updated February 12, 2026.

Round-trip from

$317
(American Airlines)

One-way from

$110
(United Airlines)

Popular in

August

Cheapest in

May

Average price

$482
From Charlottesville Albemarle to Caribbean Islands
Search Deals
One-way flight from Charlottesville Albemarle to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($24 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 Charlottesville 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 12, 2026.
Use the filters below to find and compare flights from Charlottesville to Caribbean Islands that are best for you.

Fly from

Charlottesville

Fly to

Caribbean Islands

Route

Depart

Return

Price

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Tue 4/7

7:13 pm-9:13 am

1 stop15h 00m

Montego Bay Sangster Intl

Tue 4/14

12:56 pm-8:39 am

2 stops18h 43m

$317

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 2/23

6:20 am-1:17 pm

1 stop5h 57m

San Juan Luis Munoz Marin Intl

Wed 2/25

2:05 am-5:03 pm

2 stops15h 58m

$322

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Mon 4/20

5:05 am-12:39 pm

1 stop7h 34m

Punta Cana

Thu 4/23

2:30 pm-8:39 am

2 stops18h 09m

$333

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Tue 5/26

8:00 pm-10:03 am

1 stop14h 03m

Nassau Intl

Tue 6/2

2:18 pm-8:33 am

1 stop18h 15m

$343

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 3/10

10:45 am-11:36 pm

2 stops12h 51m

San Juan Luis Munoz Marin Intl

Tue 3/17

7:05 am-1:59 pm

1 stop6h 54m

$349

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 4/16

8:03 pm-3:22 pm

2 stops19h 19m

Simpson Bay Princess Juliana

Mon 4/20

12:41 pm-9:54 am

2 stops21h 13m

$350

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 4/16

8:03 pm-1:16 pm

2 stops17h 13m

Simpson Bay Princess Juliana

Tue 4/21

12:41 pm-12:57 pm

2 stops24h 16m

$350

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 2/23

6:20 am-1:17 pm

1 stop5h 57m

San Juan Luis Munoz Marin Intl

Thu 2/26

2:05 am-5:03 pm

2 stops15h 58m

$352

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 2/23

6:00 am-5:27 pm

1 stop10h 27m

San Juan Luis Munoz Marin Intl

Tue 3/3

7:30 am-1:46 pm

1 stop7h 16m

$363

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 2/24

11:53 am-11:58 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Tue 3/3

7:30 am-4:46 pm

1 stop10h 16m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 49 results
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Best time to book a flight from Charlottesville to Caribbean Islands

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

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

Currently, January is the cheapest month in which you can book a flight from Charlottesville to Caribbean Islands (average of $73). Flying from Charlottesville to Caribbean Islands in December is currently the most expensive (average of $163). 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 12, 2026.
Read through reviews of airlines operating flights from Charlottesville to Caribbean Islands, such as United Airlines 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.
United Airlines
7.4
Good
9,276 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

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
9,276 reviews
United Airlines
7.4
Good
9,276 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

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
11,267 reviews
United Airlines
7.4
Good
9,276 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

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 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 Charlottesville to Caribbean Islands?

    If you book a flight to Caribbean Islands from Charlottesville, you will be flying from Albemarle, which is the city’s only airport. Charlottesville Albemarle (CHO) is located 7.6 mi from the center of Charlottesville.

  • How long is the flight from Charlottesville to Caribbean Islands?

    Departing from Charlottesville to Caribbean Islands will take you 5h 57m. Airlines will cover a distance of 1553 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    While some choose either Charlottesville Albemarle - Saint Thomas Island Cyril E King or Charlottesville Albemarle - Punta Cana, Charlottesville Albemarle - San Juan Luis Munoz Marin Intl is the most popular route from Charlottesville to Caribbean Islands.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Charlottesville to Caribbean Islands (average of $73). Flying from Charlottesville to Caribbean Islands in December is currently the most expensive (average of $163). 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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Top 2 airlines flying from Charlottesville to Caribbean Islands

Discover the top 2 airlines that operate flights from Charlottesville 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 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$315Average$711FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$368Average$615FlexibilityNo cancel feeOn-time69%

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