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$155+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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 October 23, 2025.

Round-trip from

$295
(American Airlines)

One-way from

$155
(United Airlines)

Popular in

August

Cheapest in

December

Average price

$575
From Charlottesville Albemarle to Caribbean
Search Deals
One-way flight from Charlottesville Albemarle to Caribbean
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Highest demand for flights based on searches. 10% potential increase in price ($65 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 October 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 October 23, 2025.

This American Airlines deal was found by Cheapflights users on 10/22. 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 12/105:56 pmSJU - CHO
1 stop15h 34mAmerican Airlines
Deal found 10/22$295
This Delta deal was found by Cheapflights users on 10/22. 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 12/811:15 amCHO - SJU
1 stop11h 05mDelta
Wed 12/107:00 amSJU - CHO
1 stop8h 23mDelta
Deal found 10/22$302
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/158:07 pmCHO - PUJ
1 stop16h 27mAmerican Airlines
Sat 11/225:44 pmPUJ - CHO
1 stop15h 46mAmerican Airlines
Deal found 10/23$302
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amCHO - GCM
1 stop6h 35mDelta
Thu 11/201:50 pmGCM - CHO
1 stop8h 57mDelta
Deal found 10/21$310
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:00 pmCHO - GCM
2 stops24h 35mDelta
Mon 11/241:50 pmGCM - CHO
1 stop8h 57mDelta
Deal found 10/21$315
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Tue 11/1812:13 pmCHO - GCM
1 stop23h 52mAmerican Airlines
Sat 11/2212:55 pmGCM - CHO
1 stop9h 09mAmerican Airlines
Deal found 10/21$316
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/288:10 pmCHO - GCM
1 stop20h 25mUnited Airlines
Tue 12/95:45 pmGCM - CHO
2 stops16h 30mUnited Airlines
Deal found 10/22$320
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/205:00 amCHO - GCM
2 stops15h 28mAmerican Airlines
Tue 11/253:10 pmGCM - CHO
1 stop17h 20mAmerican Airlines
Deal found 10/21$321
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Sat 11/18:10 pmCHO - GCM
2 stops18h 05mUnited Airlines
Wed 11/55:45 pmGCM - CHO
2 stops16h 35mUnited Airlines
Deal found 10/21$324
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/68:07 pmCHO - SDQ
2 stops16h 55mAmerican Airlines
Sat 12/133:11 pmSDQ - CHO
2 stops18h 19mAmerican Airlines
Deal found 10/22$328
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Sat 11/16:01 pmCHO - GCM
1 stop18h 56mAmerican Airlines
Wed 11/51:05 pmGCM - CHO
1 stop7h 52mAmerican Airlines
Deal found 10/21$334
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/296:10 amCHO - GCM
1 stop10h 25mUnited Airlines
Sat 12/62:25 pmGCM - CHO
2 stops19h 50mUnited Airlines
Deal found 10/22$348

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 October 23, 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

Mon 12/8

4:33 pm-10:09 am

2 stops16h 36m

San Juan Luis Munoz Marin Intl

Wed 12/10

8:20 am-1:53 pm

1 stop6h 33m

$295

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

11:15 am-11:20 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:00 am-2:23 pm

1 stop8h 23m

$302

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 11/15

8:07 pm-1:34 pm

1 stop16h 27m

Punta Cana

Sat 11/22

5:44 pm-8:30 am

1 stop15h 46m

$302

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Fri 1/23

7:09 pm-12:55 pm

1 stop16h 46m

Punta Cana

Mon 1/26

4:09 pm-9:49 am

2 stops18h 40m

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

7:09 pm-2:55 pm

2 stops18h 46m

Punta Cana

Fri 2/6

5:33 pm-9:54 am

2 stops17h 21m

$306

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Tue 11/18

6:00 am-12:35 pm

1 stop6h 35m

George Town Owen Roberts Intl

Mon 11/24

1:50 pm-10:47 pm

1 stop8h 57m

$310

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Mon 11/17

12:00 pm-12:35 pm

2 stops24h 35m

George Town Owen Roberts Intl

Thu 11/20

1:50 pm-10:47 pm

1 stop8h 57m

$315

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Mon 11/17

12:00 pm-12:35 pm

2 stops24h 35m

George Town Owen Roberts Intl

Mon 11/24

1:50 pm-10:47 pm

1 stop8h 57m

$315

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Wed 1/7

7:09 pm-2:45 pm

2 stops19h 36m

George Town Owen Roberts Intl

Wed 1/14

3:40 pm-9:49 am

2 stops18h 09m

$315

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Sat 12/6

8:07 pm-12:10 pm

2 stops16h 03m

George Town Owen Roberts Intl

Sat 12/13

3:45 pm-8:30 am

2 stops16h 45m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 36 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 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 October 23, 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 24% 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 October 23, 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
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,982 reviews
Delta
7.9
Good
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,995 reviews
Delta
7.9
Good
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,033 reviews
Delta
7.9
Good
7,982 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 $555, American Airlines can have you in Caribbean from Charlottesville in 6h 26m. The distance from Charlottesville to Caribbean is about 1590 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 - San Juan Luis Munoz Marin Intl, Charlottesville Albemarle - Punta Cana or Charlottesville Albemarle - Santo Domingo Las Americas 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 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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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$261Average$582FlexibilityNo cancel feeOn-time69%
DeltaCheapest$311Average$364FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$709FlexibilityNo cancel feeOn-time71%

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