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$109+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
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 December 30, 2025.

This American Airlines deal was found by Cheapflights users on 12/28. 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 12/306:00 amCHO - PUJ
1 stop6h 27mAmerican Airlines
Thu 1/85:26 pmPUJ - CHO
2 stops17h 33mAmerican Airlines
Deal found 12/28$352
This American Airlines deal was found by Cheapflights users on 12/28. 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 12/306:00 amCHO - GCM
1 stop5h 57mAmerican Airlines
Fri 1/21:05 pmGCM - CHO
2 stops19h 30mAmerican Airlines
Deal found 12/28$639
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/307:57 pmCHO - STT
1 stop15h 08mAmerican Airlines
Wed 12/314:34 pmSTT - CHO
1 stop17h 01mAmerican Airlines
Deal found 12/27$689
This American Airlines deal was found by Cheapflights users on 12/27. 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 12/297:57 pmCHO - STT
1 stop15h 08mAmerican Airlines
Thu 1/14:34 pmSTT - CHO
1 stop17h 01mAmerican Airlines
Deal found 12/27$711
This United Airlines deal was found by Cheapflights users on 12/28. 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 12/306:49 amCHO - SJU
2 stops13h 37mUnited Airlines
Fri 1/25:50 pmSJU - CHO
1 stop6h 54mUnited Airlines
Deal found 12/28$761
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:00 amCHO - STT
1 stop8h 52mAmerican Airlines
Tue 12/306:36 pmSTT - CHO
2 stops24h 54mAmerican Airlines
Deal found 12/27$789
This American Airlines deal was found by Cheapflights users on 12/27. 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 12/297:57 pmCHO - STT
1 stop15h 08mAmerican Airlines
Wed 12/314:34 pmSTT - CHO
1 stop17h 01mAmerican Airlines
Deal found 12/27$821
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:49 amCHO - STT
2 stops9h 53mUnited Airlines
Wed 12/311:02 pmSTT - CHO
1 stop7h 37mUnited Airlines
Deal found 12/27$825
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:00 amCHO - STT
1 stop8h 52mAmerican Airlines
Thu 1/14:34 pmSTT - CHO
1 stop17h 01mAmerican Airlines
Deal found 12/27$859
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Wed 12/316:01 pmCHO - STT
1 stop17h 04mAmerican Airlines
Thu 1/14:34 pmSTT - CHO
1 stop17h 01mAmerican Airlines
Deal found 12/27$902
This American Airlines deal was found by Cheapflights users on 12/27. 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 12/297:57 pmCHO - STT
1 stop15h 08mAmerican Airlines
Tue 12/304:34 pmSTT - CHO
1 stop6h 18mAmerican Airlines
Deal found 12/27$921
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Mon 12/298:15 pmCHO - STT
2 stops19h 03mUnited Airlines
Wed 12/315:20 pmSTT - CHO
1 stop21h 29mUnited Airlines
Deal found 12/27$949

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 December 30, 2025.

Round-trip from

$231
(American Airlines)

One-way from

$109
(Delta)

Popular in

August

Cheapest in

May

Average price

$658
From Charlottesville Albemarle to Caribbean
Search Deals
One-way flight from Charlottesville Albemarle to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 30, 2025.
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

6:06 pm-11:40 am

1 stop16h 34m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:00 am-4:25 pm

2 stops10h 25m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Wed 3/4

2:29 pm-11:58 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:15 am-1:46 pm

1 stop7h 31m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 3/3

2:29 pm-11:58 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:15 am-1:46 pm

1 stop7h 31m

$231

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 1/20

6:00 am-1:45 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Sat 1/24

3:23 pm-11:49 pm

1 stop9h 26m

$293

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 2/26

7:57 pm-4:28 pm

2 stops19h 31m

Simpson Bay Princess Juliana

Thu 3/5

3:17 pm-8:27 am

2 stops18h 10m

$298

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 1/19

4:37 pm-2:31 pm

2 stops20h 54m

Simpson Bay Princess Juliana

Fri 1/23

2:03 pm-11:19 pm

2 stops10h 16m

$298

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

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 2/28

7:57 pm-2:20 pm

2 stops17h 23m

Punta Cana

Sat 3/7

3:20 pm-7:27 am

2 stops17h 07m

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Wed 2/18

7:17 pm-12:01 pm

2 stops15h 44m

Punta Cana

Sat 2/28

3:20 pm-8:27 am

2 stops18h 07m

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

7:09 pm-2:55 pm

2 stops18h 46m

Punta Cana

Fri 2/6

5:26 pm-9:59 am

2 stops17h 33m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 39 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, June is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $86). Flying from Charlottesville to Caribbean in December is currently the most expensive (average of $167). 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 December 30, 2025.
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
9,124 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,124 reviews
United Airlines
7.4
Good
9,124 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,074 reviews
United Airlines
7.4
Good
9,124 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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 $321, American Airlines can have you in Caribbean from Charlottesville in 6h 41m. 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 - Punta Cana, Charlottesville Albemarle - San Juan Luis Munoz Marin Intl or Charlottesville Albemarle - Montego Bay Sangster 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, June is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $86). Flying from Charlottesville to Caribbean in December is currently the most expensive (average of $167). 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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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 December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$671FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$414Average$582FlexibilityNo cancel feeOn-time69%

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