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$118+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$301
(American Airlines)

One-way from

$118
(Delta)

Popular in

August

Cheapest in

December

Average price

$465
From Charlottesville Albemarle to Caribbean
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One-way flight from Charlottesville Albemarle to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($61 potential increase over avg. RT price).
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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 September 2025
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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 September 17, 2025.

This United Airlines deal was found by Cheapflights users on 9/16. 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 10/36:10 amCHO - SJU
2 stops14h 28mUnited Airlines
Tue 10/74:55 pmSJU - CHO
1 stop6h 19mUnited Airlines
Deal found 9/16$343
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/155:00 amCHO - PUJ
1 stop10h 46mAmerican Airlines
Sat 11/2212:51 pmPUJ - CHO
1 stop12h 05mAmerican Airlines
Deal found 9/15$399
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 12/84:33 pmCHO - STT
2 stops21h 53mAmerican Airlines
Wed 12/105:29 pmSTT - CHO
1 stop16h 01mAmerican Airlines
Deal found 9/14$403
This United Airlines deal was found by Cheapflights users on 9/15. 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 12/106:10 amCHO - SJU
2 stops14h 16mUnited Airlines
Sun 12/142:05 amSJU - CHO
2 stops12h 29mUnited Airlines
Deal found 9/15$405
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 9/235:40 amCHO - NAS
1 stop6h 10mDelta
Wed 9/243:14 pmNAS - CHO
1 stop8h 21mDelta
Deal found 9/16$413
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:00 amCHO - SJU
1 stop10h 23mDelta
Wed 12/103:32 pmSJU - CHO
1 stop8h 15mDelta
Deal found 9/14$420
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/12:50 pmCHO - SDQ
2 stops11h 00mUnited Airlines
Fri 10/103:20 pmSDQ - CHO
2 stops18h 33mUnited Airlines
Deal found 9/15$426
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/256:10 amCHO - SJU
1 stop6h 24mUnited Airlines
Sat 11/17:30 amSJU - CHO
1 stop6h 25mUnited Airlines
Deal found 9/15$433
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 10/2511:51 amCHO - SJU
1 stop10h 08mDelta
Sat 11/17:15 amSJU - CHO
1 stop7h 50mDelta
Deal found 9/17$435
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/188:29 pmCHO - MBJ
2 stops16h 14mUnited Airlines
Sat 10/252:40 pmMBJ - CHO
2 stops18h 13mUnited Airlines
Deal found 9/17$451
This United Airlines deal was found by Cheapflights users on 9/17. 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 11/18:10 pmCHO - PUJ
1 stop16h 49mUnited Airlines
Wed 11/512:56 pmPUJ - CHO
1 stop21h 57mUnited Airlines
Deal found 9/17$459
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:10 pmCHO - MBJ
1 stop20h 02mUnited Airlines
Fri 11/142:48 pmMBJ - CHO
2 stops28h 43mUnited Airlines
Deal found 9/14$462

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 September 17, 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

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

8:20 pm-1:20 pm

1 stop16h 00m

Punta Cana

Fri 2/6

6:20 pm-8:36 am

1 stop15h 16m

$301

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Fri 10/3

6:10 am-8:38 pm

2 stops14h 28m

San Juan Luis Munoz Marin Intl

Tue 10/7

4:55 pm-11:14 pm

1 stop6h 19m

$343

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Tue 3/10

7:00 am-2:30 pm

1 stop7h 30m

Nassau Intl

Wed 3/11

3:40 pm-10:34 pm

1 stop6h 54m

$345

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Fri 2/6

8:20 pm-9:40 am

2 stops13h 20m

Nassau Intl

Sun 2/8

7:15 pm-8:36 am

2 stops13h 21m

$366

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 11/15

5:00 am-4:46 pm

1 stop10h 46m

Punta Cana

Sat 11/22

12:51 pm-11:56 pm

1 stop12h 05m

$399

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Mon 12/8

4:33 pm-3:26 pm

2 stops21h 53m

Saint Thomas Island Cyril E King

Wed 12/10

6:17 pm-4:03 pm

2 stops22h 46m

$403

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 2/21

8:24 pm-1:35 pm

1 stop16h 11m

Punta Cana

Sat 2/28

4:40 pm-8:36 am

2 stops16h 56m

$404

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Wed 12/10

6:10 am-9:26 pm

2 stops14h 16m

San Juan Luis Munoz Marin Intl

Sun 12/14

2:05 am-1:34 pm

2 stops12h 29m

$405

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

6:00 am-5:23 pm

1 stop10h 23m

San Juan Luis Munoz Marin Intl

Wed 12/10

3:32 pm-10:47 pm

1 stop8h 15m

$420

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

4:33 pm-1:30 pm

2 stops19h 57m

San Juan Luis Munoz Marin Intl

Wed 12/10

6:00 am-4:00 pm

2 stops11h 00m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 40 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 September 17, 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 September 17, 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
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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
7,961 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

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.

  • How long is the flight from Charlottesville to Caribbean?

    For as low as $345, American Airlines can have you in Caribbean from Charlottesville in 7h 30m. 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 cheapest airlines to fly from Charlottesville to Caribbean one-way?

    The cheapest airlines for a one-way flight from Charlottesville to Caribbean are Delta ($118), United Airlines ($201), and American Airlines ($219).

  • 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 - 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, 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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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$261Average$603FlexibilityNo cancel feeOn-time69%
DeltaCheapest$311Average$364FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$425Average$690FlexibilityNo cancel feeOn-time71%

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