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$232+ Cheap flights from Charlottesville (CHO) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Round-trip from

$232
(American Airlines)

One-way from

$140
(American Airlines)

Popular in

August

Cheapest in

May

Average price

$765
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. 5% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This American Airlines deal was found by Cheapflights users on 1/6. 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 2/226:15 amCHO - SJU
1 stop14h 34mAmerican Airlines
Wed 2/258:40 amSJU - CHO
1 stop9h 25mAmerican Airlines
Deal found 1/6$232
This United Airlines deal was found by Cheapflights users on 1/6. 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 2/12:41 pmCHO - SJU
1 stop6h 41mUnited Airlines
Mon 2/22:05 amSJU - CHO
2 stops12h 37mUnited Airlines
Deal found 1/6$255
This Delta deal was found by Cheapflights users on 1/8. 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 3/102:27 pmCHO - SJU
1 stop5h 51mDelta
Tue 3/177:30 amSJU - CHO
1 stop6h 16mDelta
Deal found 1/8$266
This American Airlines deal was found by Cheapflights users on 1/8. 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 1/277:10 amCHO - SJU
1 stop12h 40mAmerican Airlines
Fri 1/305:55 pmSJU - CHO
1 stop17h 04mAmerican Airlines
Deal found 1/8$277
This United Airlines deal was found by Cheapflights users on 1/8. 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 1/278:15 amCHO - SJU
2 stops12h 11mUnited Airlines
Fri 1/308:10 amSJU - CHO
2 stops13h 47mUnited Airlines
Deal found 1/8$300
This American Airlines deal was found by Cheapflights users on 1/8. 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 3/157:57 pmCHO - GCM
2 stops16h 08mAmerican Airlines
Fri 3/2011:40 amGCM - CHO
2 stops19h 47mAmerican Airlines
Deal found 1/8$302
This United Airlines deal was found by Cheapflights users on 1/7. 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 1/202:41 pmCHO - SJU
1 stop6h 41mUnited Airlines
Tue 1/272:05 amSJU - CHO
2 stops12h 37mUnited Airlines
Deal found 1/7$305
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/17:09 pmCHO - PUJ
2 stops18h 46mAmerican Airlines
Fri 2/64:09 pmPUJ - CHO
2 stops18h 50mAmerican Airlines
Deal found 1/7$307
This American Airlines deal was found by Cheapflights users on 1/7. 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 3/27:57 pmCHO - PUJ
2 stops18h 58mAmerican Airlines
Sun 3/82:20 pmPUJ - CHO
2 stops18h 07mAmerican Airlines
Deal found 1/7$312
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/216:06 pmCHO - PUJ
2 stops16h 55mAmerican Airlines
Tue 3/35:01 pmPUJ - CHO
1 stop17h 46mAmerican Airlines
Deal found 1/7$313
This United Airlines deal was found by Cheapflights users on 1/7. 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 3/106:45 amCHO - STT
1 stop8h 33mUnited Airlines
Tue 3/172:05 pmSTT - CHO
1 stop10h 04mUnited Airlines
Deal found 1/7$316
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/267:57 pmCHO - SXM
2 stops19h 31mAmerican Airlines
Thu 3/51:29 pmSXM - CHO
2 stops19h 58mAmerican Airlines
Deal found 1/7$316

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 January 8, 2026.
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 2/1

2:17 pm-6:11 am

2 stops14h 54m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:05 am-1:42 pm

2 stops12h 37m

$232

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sun 2/22

7:57 pm-1:53 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

Wed 2/25

8:40 am-6:52 pm

1 stop11h 12m

$232

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 3/10

2:27 pm-8:18 pm

1 stop5h 51m

San Juan Luis Munoz Marin Intl

Tue 3/17

7:30 am-1:46 pm

1 stop6h 16m

$266

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 1/27

2:41 pm-10:22 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:10 am-8:57 pm

2 stops13h 47m

$300

CharlottesvilleGeorge Town

CHO - GCM

CHOGCM

Charlottesville Albemarle

Sun 3/15

7:57 pm-11:05 am

2 stops16h 08m

George Town Owen Roberts Intl

Fri 3/20

11:40 am-8:27 am

2 stops19h 47m

$302

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 1/20

11:58 am-11:45 pm

1 stop10h 47m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:30 am-2:12 pm

1 stop7h 42m

$305

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 1/20

2:41 pm-10:22 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Wed 1/28

8:10 am-1:54 pm

1 stop6h 44m

$305

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 2/21

6:06 pm-12:01 pm

2 stops16h 55m

Punta Cana

Tue 3/3

5:54 pm-1:39 pm

2 stops20h 45m

$307

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

7:09 pm-12:55 pm

1 stop16h 46m

Punta Cana

Fri 2/6

4:09 pm-9:59 am

2 stops18h 50m

$307

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sat 2/21

7:57 pm-2:20 pm

2 stops17h 23m

Punta Cana

Sat 2/28

3:20 pm-8:27 am

2 stops18h 07m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 34 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, January is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $73). Flying from Charlottesville to Caribbean in December is currently the most expensive (average of $166). 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.

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 January 8, 2026.
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
9,139 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,139 reviews
United Airlines
7.4
Good
9,139 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
American Airlines
7.2
Good
11,095 reviews
United Airlines
7.4
Good
9,139 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

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 $326, United Airlines can have you in Caribbean from Charlottesville in 5h 04m. 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 - Montego Bay Sangster Intl or Charlottesville Albemarle - San Juan Luis Munoz Marin 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, January is the cheapest month in which you can book a flight from Charlottesville to Caribbean (average of $73). Flying from Charlottesville to Caribbean in December is currently the most expensive (average of $166). 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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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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$672FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$414Average$582FlexibilityNo cancel feeOn-time69%

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