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Caribbean Islands

$155+ Cheap flights from Charlottesville (CHO) to Caribbean Islands

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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Find flight deals from Charlottesville to Caribbean Islands

Cheapest flights from Charlottesville to Caribbean Islands
Explore the most affordable flight options available from Charlottesville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2025.

This American Airlines deal was found by Cheapflights users on 11/5. 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 11/156:03 pmCHO - PUJ
1 stop16h 37mAmerican Airlines
Sat 11/225:44 pmPUJ - CHO
1 stop15h 46mAmerican Airlines
Deal found 11/5$318
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/125:38 pmCHO - MBJ
2 stops20h 51mUnited Airlines
Wed 11/193:36 pmMBJ - CHO
2 stops18h 44mUnited Airlines
Deal found 11/5$324
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:09 pmCHO - SJU
1 stop7h 11mDelta
Wed 12/107:00 amSJU - CHO
1 stop11h 23mDelta
Deal found 11/4$335
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/126:05 amCHO - MBJ
1 stop6h 56mAmerican Airlines
Wed 11/192:01 pmMBJ - CHO
1 stop9h 34mAmerican Airlines
Deal found 11/5$379
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Mon 12/84:33 pmCHO - SJU
2 stops16h 36mAmerican Airlines
Wed 12/108:20 amSJU - CHO
1 stop9h 30mAmerican Airlines
Deal found 11/3$420
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Fri 11/78:10 pmCHO - MBJ
2 stops18h 19mUnited Airlines
Fri 11/143:36 pmMBJ - CHO
2 stops21h 59mUnited Airlines
Deal found 11/4$445
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:57 pmCHO - NAS
1 stop20h 16mAmerican Airlines
Sun 12/285:15 pmNAS - CHO
1 stop15h 20mAmerican Airlines
Deal found 11/4$516
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Fri 12/196:10 amCHO - MBJ
1 stop10h 02mUnited Airlines
Fri 12/265:14 pmMBJ - CHO
1 stop6h 30mUnited Airlines
Deal found 11/3$518
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/2110:50 amCHO - NAS
2 stops26h 43mUnited Airlines
Sun 12/281:05 pmNAS - CHO
1 stop10h 39mUnited Airlines
Deal found 11/4$519
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/86:10 amCHO - SJU
1 stop6h 07mUnited Airlines
Tue 12/92:05 amSJU - CHO
2 stops12h 29mUnited Airlines
Deal found 11/3$532
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Wed 11/196:10 amCHO - SJU
2 stops14h 16mUnited Airlines
Sat 11/222:05 amSJU - CHO
2 stops15h 53mUnited Airlines
Deal found 11/4$573
This American Airlines deal was found by Cheapflights users on 11/4. 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 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 12/233:39 pmPUJ - CHO
2 stops17h 56mAmerican Airlines
Deal found 11/4$582

Cheap flight deals from Charlottesville to Caribbean Islands

Keep the following information in mind while searching for Charlottesville to Caribbean Islands flight deals. Data was last updated November 5, 2025.

Round-trip from

$235
(Delta)

One-way from

$167
(United Airlines)

Popular in

August

Cheapest in

December

Average price

$528
From Charlottesville Albemarle to Caribbean Islands
Search Deals
One-way flight from Charlottesville Albemarle to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Charlottesville to Caribbean Islands 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 November 5, 2025.
Use the filters below to find and compare flights from Charlottesville to Caribbean Islands that are best for you.

Fly from

Charlottesville

Fly to

Caribbean Islands

Route

Depart

Return

Price

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 1/27

6:00 am-1:08 pm

1 stop6h 08m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:55 pm-9:59 am

1 stop17h 04m

$235

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 1/27

8:15 am-12:36 am

2 stops15h 21m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-1:42 pm

2 stops12h 37m

$283

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 2/21

7:57 pm-2:55 pm

2 stops17h 58m

Punta Cana

Tue 3/3

5:57 pm-9:43 am

2 stops16h 46m

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Wed 1/21

7:09 pm-2:55 pm

2 stops18h 46m

Punta Cana

Sat 1/24

3:43 pm-9:59 am

2 stops19h 16m

$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-11:58 am

2 stops18h 56m

$306

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Fri 1/16

7:00 am-11:00 am

2 stops28h 00m

George Town Owen Roberts Intl

Fri 1/23

3:55 pm-2:50 pm

2 stops22h 55m

$315

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Wed 1/7

7:09 pm-11:50 am

2 stops16h 41m

George Town Owen Roberts Intl

Wed 1/14

3:45 pm-11:58 am

2 stops20h 13m

$315

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 1/31

5:20 pm-12:58 pm

2 stops18h 38m

Simpson Bay Princess Juliana

Sat 2/7

2:03 pm-9:59 am

2 stops20h 56m

$316

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 11/15

6:03 pm-11:40 am

1 stop16h 37m

Punta Cana

Sat 11/22

5:44 pm-8:30 am

1 stop15h 46m

$318

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 1/30

4:37 pm-12:58 pm

2 stops19h 21m

Simpson Bay Princess Juliana

Sun 2/8

2:03 pm-11:58 am

2 stops22h 55m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 37 results
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Best time to book a flight from Charlottesville to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Charlottesville to Caribbean Islands?

Currently, June is the cheapest month in which you can book a flight from Charlottesville to Caribbean Islands (average of $87). Flying from Charlottesville to Caribbean Islands 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 EPX?

Find hourly flight availability from Charlottesville to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 5, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 24% on flights from Charlottesville to Caribbean Islands by exploring options for tickets in the evening.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated November 5, 2025.
Read through reviews of airlines operating flights from Charlottesville to Caribbean Islands, such as United Airlines and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,002 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,002 reviews
United Airlines
7.4
Good
9,002 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,042 reviews
United Airlines
7.4
Good
9,002 reviews

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from Charlottesville to Caribbean Islands. 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 Islands?

    If you book a flight to Caribbean Islands from Charlottesville, you will be flying from Albemarle, which is the city’s only airport. Charlottesville Albemarle (CHO) is located 7.6 mi from the center of Charlottesville.

  • How long is the flight from Charlottesville to Caribbean Islands?

    Departing from Charlottesville to Caribbean Islands will take you 6h 08m. Airlines will cover a distance of 1553 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Charlottesville to Caribbean Islands one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $155. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Charlottesville to Caribbean Islands for a low price.

  • What are the most popular routes from Charlottesville to Caribbean Islands?

    While some choose either Charlottesville Albemarle - Santo Domingo Las Americas or Charlottesville Albemarle - San Juan Luis Munoz Marin Intl, Charlottesville Albemarle - Punta Cana is the most popular route from Charlottesville to Caribbean Islands.

  • Can I find deals for flights from Charlottesville to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Charlottesville to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Charlottesville to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Charlottesville to Caribbean Islands.

  • Can I find deals for business class flights from Charlottesville to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Charlottesville to Caribbean Islands 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 Islands?

    Currently, June is the cheapest month in which you can book a flight from Charlottesville to Caribbean Islands (average of $87). Flying from Charlottesville to Caribbean Islands 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

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Top 3 airlines flying from Charlottesville to Caribbean Islands

Discover the top 3 airlines that operate flights from Charlottesville to Caribbean Islands. 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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$261Average$582FlexibilityNo cancel feeOn-time69%
DeltaCheapest$311Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$688FlexibilityNo cancel feeOn-time71%

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