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$116+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. 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 4/136:20 am
CHO
-
SJU
1 stop6h 14m
United Airlines
Thu 4/161:00 am
SJU
-
CHO
2 stops8h 58m
United Airlines
Deal found 1/28$274
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 3/58:29 pm
CHO
-
MBJ
2 stops17h 17m
United Airlines
Sun 3/81:48 pm
MBJ
-
CHO
1 stop9h 21m
United Airlines
Deal found 1/27$316
This Delta deal was found by Cheapflights users on 1/27. 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.
Mon 2/237:00 am
CHO
-
NAS
1 stop8h 13m
Delta
Thu 2/264:23 pm
NAS
-
CHO
1 stop6h 24m
Delta
Deal found 1/27$322
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/216:06 pm
CHO
-
PUJ
2 stops16h 55m
American Airlines
Tue 3/33:20 pm
PUJ
-
CHO
2 stops19h 27m
American Airlines
Deal found 1/27$323
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 2/236:06 pm
CHO
-
NAS
2 stops16h 52m
American Airlines
Thu 2/266:04 pm
NAS
-
CHO
2 stops14h 23m
American Airlines
Deal found 1/27$328
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 3/27:57 pm
CHO
-
SXM
1 stop17h 19m
American Airlines
Fri 3/2712:29 pm
SXM
-
CHO
2 stops19h 58m
American Airlines
Deal found 1/27$335
This American Airlines deal was found by Cheapflights users on 1/28. 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
1 stop15h 00m
American Airlines
Tue 4/1412:51 pm
MBJ
-
CHO
2 stops18h 48m
American Airlines
Deal found 1/28$337
This Delta deal was found by Cheapflights users on 1/27. 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.
Sun 2/86:00 am
CHO
-
SJU
1 stop6h 06m
Delta
Thu 2/196:15 am
SJU
-
CHO
1 stop8h 31m
Delta
Deal found 1/27$339
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/47:09 pm
CHO
-
GCM
2 stops19h 36m
American Airlines
Sun 2/83:45 pm
GCM
-
CHO
2 stops18h 14m
American Airlines
Deal found 1/28$339
This United Airlines deal was found by Cheapflights users on 1/28. 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 4/76:20 am
CHO
-
MBJ
1 stop9h 50m
United Airlines
Tue 4/144:12 pm
MBJ
-
CHO
1 stop16h 46m
United Airlines
Deal found 1/28$340
This United Airlines deal was found by Cheapflights users on 1/28. 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 2/910:35 am
CHO
-
SJU
2 stops13h 01m
United Airlines
Tue 2/102:05 am
SJU
-
CHO
2 stops12h 37m
United Airlines
Deal found 1/28$350
This Faresmojo deal was found by Cheapflights users on 1/26. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/66:00 am
CHO
-
SJU
1 stop7h 31m
JetBlue
Sun 2/87:30 am
SJU
-
CHO
1 stop8h 18m
JetBlue
Deal found 1/26$352

Find 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 29, 2026.

Round-trip from

$232
(Delta)

One-way from

$116
(Delta)

Popular in

August

Cheapest in

May

Average price

$624
From Charlottesville Albemarle to Caribbean
Search Deals
One-way flight from Charlottesville Albemarle to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 29, 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

Mon 4/13

6:20 am-12:34 pm

1 stop6h 14m

San Juan Luis Munoz Marin Intl

Thu 4/16

1:00 am-9:58 am

2 stops8h 58m

$274

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Thu 3/5

8:29 pm-1:46 pm

2 stops17h 17m

Montego Bay Sangster Intl

Sun 3/8

1:48 pm-12:09 am

1 stop9h 21m

$316

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Mon 2/23

7:00 am-3:13 pm

1 stop8h 13m

Nassau Intl

Thu 2/26

4:23 pm-10:47 pm

1 stop6h 24m

$322

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 2/21

6:06 pm-11:34 am

1 stop16h 28m

Punta Cana

Tue 3/3

3:20 pm-9:47 am

2 stops19h 27m

$323

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Mon 2/23

6:06 pm-10:58 am

2 stops16h 52m

Nassau Intl

Thu 2/26

6:04 pm-8:27 am

2 stops14h 23m

$328

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 3/2

5:00 pm-2:19 pm

2 stops20h 19m

Simpson Bay Princess Juliana

Fri 3/27

12:29 pm-8:27 am

2 stops19h 58m

$335

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Tue 4/7

5:16 pm-11:51 am

2 stops19h 35m

Montego Bay Sangster Intl

Tue 4/14

12:51 pm-8:39 am

2 stops18h 48m

$337

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sun 2/8

6:00 am-1:06 pm

1 stop6h 06m

San Juan Luis Munoz Marin Intl

Thu 2/19

6:15 am-1:46 pm

1 stop8h 31m

$339

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Tue 4/7

6:20 am-3:10 pm

1 stop9h 50m

Montego Bay Sangster Intl

Tue 4/14

4:12 pm-9:58 am

1 stop16h 46m

$340

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 2/9

10:35 am-12:36 am

2 stops13h 01m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-1:54 pm

2 stops12h 49m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 45 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 $81). 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 29, 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
9,215 reviews

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

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
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

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
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

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 $274, United Airlines can have you in Caribbean from Charlottesville in 6h 14m. The distance from Charlottesville to Caribbean is about 1553 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 - San Juan Luis Munoz Marin Intl, Charlottesville Albemarle - Saint Thomas Island Cyril E King or Charlottesville Albemarle - Punta Cana 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 $81). 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

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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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$329Average$649FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$414Average$559FlexibilityNo cancel feeOn-time69%

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