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$107+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/3. 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 12/186:01 pmCHO - PUJ
2 stops17h 09mAmerican Airlines
Tue 12/231:15 pmPUJ - CHO
2 stops20h 20mAmerican Airlines
Deal found 12/3$616
This United Airlines deal was found by Cheapflights users on 12/3. 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 12/318:15 pmCHO - SXM
1 stop16h 35mUnited Airlines
Wed 1/72:52 pmSXM - CHO
2 stops24h 02mUnited Airlines
Deal found 12/3$666
This United Airlines deal was found by Cheapflights users on 12/4. 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 12/145:33 pmCHO - SDQ
2 stops20h 33mUnited Airlines
Wed 12/172:53 pmSDQ - CHO
2 stops19h 58mUnited Airlines
Deal found 12/4$737
This United Airlines deal was found by Cheapflights users on 12/3. 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 12/155:33 pmCHO - SDQ
2 stops20h 33mUnited Airlines
Thu 12/184:18 pmSDQ - CHO
2 stops18h 33mUnited Airlines
Deal found 12/3$744
This United Airlines deal was found by Cheapflights users on 12/2. 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 12/176:10 amCHO - SJU
2 stops13h 50mUnited Airlines
Sun 12/218:10 amSJU - CHO
2 stops12h 29mUnited Airlines
Deal found 12/2$757
This American Airlines deal was found by Cheapflights users on 12/3. 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 12/246:00 amCHO - SXM
2 stops30h 26mAmerican Airlines
Sun 12/283:28 pmSXM - CHO
2 stops18h 07mAmerican Airlines
Deal found 12/3$766
This United Airlines deal was found by Cheapflights users on 12/4. 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 12/97:00 amCHO - SDQ
2 stops15h 46mUnited Airlines
Fri 12/126:00 amSDQ - CHO
2 stops15h 48mUnited Airlines
Deal found 12/4$770
This American Airlines deal was found by Cheapflights users on 12/2. 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 - NAS
2 stops16h 05mAmerican Airlines
Sun 1/46:45 pmNAS - CHO
2 stops13h 50mAmerican Airlines
Deal found 12/2$776
This United Airlines deal was found by Cheapflights users on 12/2. 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 12/242:45 pmCHO - SJU
1 stop6h 37mUnited Airlines
Wed 12/318:10 amSJU - CHO
2 stops12h 29mUnited Airlines
Deal found 12/2$822
This Delta deal was found by Cheapflights users on 12/2. 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.
Wed 12/318:15 amCHO - NAS
1 stop6h 15mDelta
Sun 1/48:10 amNAS - CHO
1 stop5h 35mDelta
Deal found 12/2$822
This American Airlines deal was found by Cheapflights users on 12/3. 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 12/136:04 pmCHO - SDQ
2 stops17h 24mAmerican Airlines
Sat 1/104:47 pmSDQ - CHO
2 stops18h 12mAmerican Airlines
Deal found 12/3$834
This United Airlines deal was found by Cheapflights users on 12/2. 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 12/242:45 pmCHO - SJU
1 stop6h 37mUnited Airlines
Mon 12/298:10 amSJU - CHO
1 stop27h 05mUnited Airlines
Deal found 12/2$887

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 4, 2025.

Round-trip from

$231
(Delta)

One-way from

$107
(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. 7% potential increase in price ($46 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
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 December 4, 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 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

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 1/31

5:20 pm-4:28 pm

2 stops22h 08m

Simpson Bay Princess Juliana

Wed 2/4

3:31 pm-11:58 am

2 stops21h 27m

$298

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 1/29

7:09 pm-3:22 pm

2 stops19h 13m

Simpson Bay Princess Juliana

Mon 2/2

5:33 pm-11:58 am

2 stops19h 25m

$298

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 1/23

4:37 pm-12:58 pm

2 stops19h 21m

Simpson Bay Princess Juliana

Mon 1/26

4:24 pm-11:19 pm

1 stop7h 55m

$298

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 1/30

7:09 pm-2:22 pm

1 stop18h 13m

Simpson Bay Princess Juliana

Tue 2/3

3:31 pm-11:58 am

2 stops21h 27m

$304

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 1/30

7:09 pm-2:22 pm

1 stop18h 13m

Simpson Bay Princess Juliana

Mon 2/2

5:33 pm-9:59 am

2 stops17h 26m

$304

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 1/24

3:13 pm-1:42 pm

1 stop21h 29m

Simpson Bay Princess Juliana

Tue 1/27

5:33 pm-9:59 am

2 stops17h 26m

$304

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 2/21

7:57 pm-11:38 am

1 stop14h 41m

Punta Cana

Tue 3/3

1:04 pm-9:49 am

2 stops21h 45m

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Wed 2/18

7:17 pm-2:58 pm

2 stops18h 41m

Punta Cana

Sat 2/28

3:34 pm-8:35 am

2 stops18h 01m

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

7:09 pm-12:55 pm

1 stop16h 46m

Punta Cana

Fri 2/6

6:02 pm-9:59 am

2 stops16h 57m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 49 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 $87). Flying from Charlottesville to Caribbean in September is currently the most expensive (average of $160). 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 4, 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 4, 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
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,011 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,066 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,047 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 $346, Delta can have you in Caribbean from Charlottesville in 7h 07m. The distance from Charlottesville to Caribbean is about 906 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 $87). Flying from Charlottesville to Caribbean in September is currently the most expensive (average of $160). 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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Alternative routes for Charlottesville to Caribbean

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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$261Average$609FlexibilityNo cancel feeOn-time69%
DeltaCheapest$311Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$681FlexibilityNo cancel feeOn-time71%

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