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$215+ Cheap flights from Charlottesville (CHO) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$215
(American Airlines)

Popular in

August

Cheapest in

November

Average price

$790
From Charlottesville Albemarle to Caribbean
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($138 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 August 2025
Search Deals

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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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 10/256:01 pmCHO - SJU
1 stop5h 53mAmerican Airlines
Sat 11/13:50 pmSJU - CHO
1 stop6h 22mAmerican Airlines
Deal found 8/14$215
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/276:51 pmCHO - NAS
2 stops14h 54mAmerican Airlines
Sat 10/46:48 pmNAS - CHO
2 stops16h 00mAmerican Airlines
Deal found 8/13$376
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/274:53 pmCHO - MBJ
2 stops20h 12mAmerican Airlines
Sat 10/42:38 pmMBJ - CHO
2 stops19h 10mAmerican Airlines
Deal found 8/12$397
This American Airlines deal was found by Cheapflights users on 8/14. 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 12/95:00 amCHO - MBJ
1 stop11h 00mAmerican Airlines
Sun 12/146:00 pmMBJ - CHO
1 stop14h 37mAmerican Airlines
Deal found 8/14$398
This American Airlines deal was found by Cheapflights users on 8/13. 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 12/88:54 amCHO - SJU
1 stop10h 51mAmerican Airlines
Wed 12/104:45 pmSJU - CHO
1 stop16h 52mAmerican Airlines
Deal found 8/13$410
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/288:04 pmCHO - MBJ
2 stops17h 01mAmerican Airlines
Sun 10/53:36 pmMBJ - CHO
2 stops17h 55mAmerican Airlines
Deal found 8/14$448
This United Airlines deal was found by Cheapflights users on 8/13. 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 10/238:29 pmCHO - PUJ
2 stops17h 36mUnited Airlines
Sun 10/264:20 pmPUJ - CHO
1 stop7h 22mUnited Airlines
Deal found 8/13$457
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/285:00 amCHO - GCM
1 stop7h 22mAmerican Airlines
Sun 10/512:28 pmGCM - CHO
1 stop10h 49mAmerican Airlines
Deal found 8/14$470
This American Airlines deal was found by Cheapflights users on 8/13. 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 12/88:54 amCHO - GCM
1 stop7h 37mAmerican Airlines
Fri 12/125:35 pmGCM - CHO
1 stop15h 02mAmerican Airlines
Deal found 8/13$474
This American Airlines deal was found by Cheapflights users on 8/13. 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 10/237:57 pmCHO - PUJ
2 stops19h 20mAmerican Airlines
Sun 10/2612:35 pmPUJ - CHO
2 stops19h 56mAmerican Airlines
Deal found 8/13$476
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 9/278:29 pmCHO - NAS
2 stops17h 02mUnited Airlines
Sat 10/42:53 pmNAS - CHO
2 stops19h 00mUnited Airlines
Deal found 8/13$521
This United Airlines deal was found by Cheapflights users on 8/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:10 amCHO - GCM
2 stops34h 20mUnited Airlines
Fri 12/125:45 pmGCM - CHO
2 stops40h 08mUnited Airlines
Deal found 8/12$533

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 August 14, 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

Sat 10/25

6:01 pm-11:54 pm

1 stop5h 53m

San Juan Luis Munoz Marin Intl

Sat 11/1

3:50 pm-10:12 pm

1 stop6h 22m

$215

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

8:20 pm-11:40 am

1 stop14h 20m

Punta Cana

Fri 2/6

6:05 pm-12:30 pm

2 stops19h 25m

$366

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Sat 9/27

6:51 pm-9:45 am

2 stops14h 54m

Nassau Intl

Sat 10/4

6:48 pm-10:48 am

2 stops16h 00m

$376

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Sat 9/27

4:53 pm-12:05 pm

2 stops20h 12m

Montego Bay Sangster Intl

Sat 10/4

2:38 pm-10:48 am

2 stops19h 10m

$397

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Tue 12/9

5:00 am-4:00 pm

1 stop11h 00m

Montego Bay Sangster Intl

Sun 12/14

6:00 pm-8:37 am

1 stop14h 37m

$398

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

8:54 am-8:45 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Wed 12/10

12:45 pm-9:50 pm

1 stop10h 05m

$410

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Sun 9/28

8:04 pm-12:05 pm

2 stops17h 01m

Montego Bay Sangster Intl

Sun 10/5

3:36 pm-10:31 am

2 stops17h 55m

$448

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Sat 1/10

8:20 pm-12:00 pm

1 stop15h 40m

George Town Owen Roberts Intl

Fri 3/6

3:45 pm-11:48 pm

1 stop8h 03m

$465

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Sun 9/28

5:00 am-11:22 am

1 stop7h 22m

George Town Owen Roberts Intl

Sun 10/5

12:28 pm-12:17 am

1 stop10h 49m

$470

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Mon 12/8

5:00 am-12:05 pm

1 stop7h 05m

George Town Owen Roberts Intl

Fri 12/12

5:35 pm-8:37 am

1 stop15h 02m

$474

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 35 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, September is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $254). Flying from Charlottesville to Caribbean in June is currently the most expensive (average of $339). 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.

What is the cheapest time of day to fly from CHO to CB?

Find hourly flight availability from Charlottesville to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Charlottesville to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 August 14, 2025.
Get a feel of what it's like to fly with Delta, 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.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 - Punta Cana or Charlottesville Albemarle - Simpson Bay Princess Juliana 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, September is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $254). Flying from Charlottesville to Caribbean in June is currently the most expensive (average of $339). 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 3 airlines flying from Charlottesville to Caribbean

Discover the top 3 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$261Average$648FlexibilityNo cancel feeOn-time69%
DeltaCheapest$311Average$410FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$425Average$706FlexibilityNo cancel feeOn-time71%

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