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$156+ 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 20 — Jan 271
Tue 1/20
Tue 1/27
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 21, 2025.

This American Airlines deal was found by Cheapflights users on 12/19. 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 stop9h 44mAmerican Airlines
Thu 1/84:09 pmPUJ - CHO
2 stops18h 50mAmerican Airlines
Deal found 12/19$314
This United Airlines deal was found by Cheapflights users on 12/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:10 amCHO - SXM
1 stop6h 40mUnited Airlines
Tue 12/234:55 pmSXM - CHO
1 stop7h 49mUnited Airlines
Deal found 12/18$453
This United Airlines deal was found by Cheapflights users on 12/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:10 amCHO - SXM
1 stop6h 40mUnited Airlines
Mon 12/224:55 pmSXM - CHO
1 stop17h 56mUnited Airlines
Deal found 12/18$459
This United Airlines deal was found by Cheapflights users on 12/19. 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.
Fri 12/266:10 amCHO - NAS
1 stop5h 40mUnited Airlines
Tue 12/301:05 pmNAS - CHO
1 stop6h 34mUnited Airlines
Deal found 12/19$617
This United Airlines deal was found by Cheapflights users on 12/19. 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 12/2010:50 amCHO - SXM
2 stops28h 07mUnited Airlines
Tue 12/234:55 pmSXM - CHO
1 stop7h 49mUnited Airlines
Deal found 12/19$641
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Fri 12/196:01 pmCHO - SXM
2 stops19h 09mAmerican Airlines
Tue 12/233:28 pmSXM - CHO
2 stops18h 07mAmerican Airlines
Deal found 12/18$682
This American Airlines deal was found by Cheapflights users on 12/19. 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.
Fri 12/197:57 pmCHO - SXM
1 stop17h 02mAmerican Airlines
Mon 12/222:59 pmSXM - CHO
1 stop7h 53mAmerican Airlines
Deal found 12/19$707
This American Airlines deal was found by Cheapflights users on 12/20. 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 12/277:57 pmCHO - NAS
1 stop20h 16mAmerican Airlines
Sat 1/36:45 pmNAS - CHO
2 stops13h 50mAmerican Airlines
Deal found 12/20$1,048
This American Airlines deal was found by Cheapflights users on 12/21. 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 - GCM
2 stops16h 08mAmerican Airlines
Sat 1/37:30 amGCM - CHO
2 stops14h 22mAmerican Airlines
Deal found 12/21$1,129
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/286:00 amCHO - SJU
1 stop6h 54mAmerican Airlines
Sun 1/46:15 pmSJU - CHO
1 stop15h 20mAmerican Airlines
Deal found 12/21$1,143
This United Airlines deal was found by Cheapflights users on 12/19. 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.
Sun 12/216:49 amCHO - STT
1 stop8h 29mUnited Airlines
Mon 1/55:20 pmSTT - CHO
2 stops21h 22mUnited Airlines
Deal found 12/19$1,173
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Sun 12/282:45 pmCHO - SJU
2 stops8h 51mUnited Airlines
Sun 1/48:30 amSJU - CHO
1 stop6h 19mUnited Airlines
Deal found 12/21$1,191

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 21, 2025.

Round-trip from

$231
(Delta)

One-way from

$156
(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 21, 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

Thu 1/22

11:58 am-8:58 pm

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:30 am-2:12 pm

1 stop7h 42m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sun 1/25

5:39 pm-6:11 am

2 stops11h 32m

San Juan Luis Munoz Marin Intl

Thu 1/29

8:10 am-1:54 pm

1 stop6h 44m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Thu 1/22

11:58 am-8:58 pm

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:30 am-2:12 pm

1 stop7h 42m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sat 1/24

4:00 pm-11:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-2:12 pm

1 stop7h 42m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sun 1/25

3:02 pm-11:45 pm

1 stop7h 43m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-2:12 pm

1 stop7h 42m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sat 1/24

11:58 am-11:45 pm

1 stop10h 47m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:51 pm

1 stop7h 56m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Fri 1/23

3:02 pm-11:45 pm

1 stop7h 43m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:51 pm

1 stop7h 56m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 4/28

2:29 pm-10:54 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Thu 4/30

6:15 am-1:49 pm

1 stop7h 34m

$265

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 1/20

7:09 pm-4:28 pm

2 stops20h 19m

Simpson Bay Princess Juliana

Sat 1/24

2:03 pm-9:59 am

2 stops20h 56m

$298

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Mon 1/12

5:20 pm-12:05 pm

2 stops18h 45m

George Town Owen Roberts Intl

Thu 1/15

3:45 pm-11:58 am

2 stops20h 13m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

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, 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 $165). 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 December 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Charlottesville to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight in the morning.

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 21, 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
9,100 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

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
9,100 reviews
United Airlines
7.4
Good
9,100 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

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
11,050 reviews
United Airlines
7.4
Good
9,100 reviews

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

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 $231, Delta can have you in Caribbean from Charlottesville in 8h. 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 - Nassau 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 $165). 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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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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$675FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$414Average$606FlexibilityNo cancel feeOn-time69%

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