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$224+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$275
(Delta)

One-way from

$224
(American Airlines)

Popular in

July

Cheapest in

November

Average price

$692
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. 14% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Delta deal was found by Cheapflights users on 7/1. 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 11/123:05 pmCHO - SJU
1 stop7h 12mDelta
Tue 11/187:30 amSJU - CHO
1 stop10h 17mDelta
Deal found 7/1$275
This deal was found by Cheapflights users on 7/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:30 amCHO - SJU
1 stop5h 47mUnited Airlines
Mon 11/105:50 pmSJU - CHO
1 stop6h 10mUnited Airlines
Deal found 7/2$341
This American Airlines deal was found by Cheapflights users on 7/3. 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 7/177:50 amCHO - SJU
1 stop16h 05mAmerican Airlines
Mon 7/213:45 pmSJU - CHO
1 stop16h 43mAmerican Airlines
Deal found 7/3$431
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 9/46:10 amCHO - PUJ
1 stop6h 30mUnited Airlines
Mon 9/84:35 pmPUJ - CHO
1 stop7h 09mUnited Airlines
Deal found 7/1$431
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 8/159:32 amCHO - MBJ
1 stop27h 48mAmerican Airlines
Fri 8/2211:45 amMBJ - CHO
1 stop19h 48mAmerican Airlines
Deal found 7/1$438
This Delta deal was found by Cheapflights users on 7/2. 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.
Mon 12/86:00 amCHO - STT
1 stop7h 22mDelta
Wed 12/103:32 pmSTT - CHO
1 stop8h 07mDelta
Deal found 7/2$537
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Tue 11/45:00 amCHO - ELH
2 stops8h 20mAmerican Airlines
Wed 11/52:50 pmELH - CHO
2 stops17h 45mAmerican Airlines
Deal found 7/2$590
This American Airlines deal was found by Cheapflights users on 7/1. 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 10/225:14 pmCHO - SXM
2 stops21h 56mAmerican Airlines
Sun 10/264:25 pmSXM - CHO
2 stops21h 29mAmerican Airlines
Deal found 7/1$597
This Delta deal was found by Cheapflights users on 7/2. 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.
Fri 10/106:00 amCHO - SXM
1 stop7h 47mDelta
Wed 10/153:15 pmSXM - CHO
1 stop7h 24mDelta
Deal found 7/2$600
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/145:00 amCHO - STT
1 stop6h 06mAmerican Airlines
Thu 8/215:10 pmSTT - CHO
2 stops21h 17mAmerican Airlines
Deal found 7/1$615
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Sat 10/188:29 pmCHO - MBJ
2 stops16h 14mUnited Airlines
Sat 10/252:40 pmMBJ - CHO
2 stops17h 46mUnited Airlines
Deal found 7/2$670
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Mon 8/256:10 amCHO - SDQ
2 stops19h 40mUnited Airlines
Fri 8/293:20 pmSDQ - CHO
2 stops18h 27mUnited Airlines
Deal found 7/2$686

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 July 3, 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

Wed 11/12

3:05 pm-11:17 pm

1 stop7h 12m

San Juan Luis Munoz Marin Intl

Tue 11/18

7:30 am-4:47 pm

1 stop10h 17m

$275

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 11/4

6:30 am-1:17 pm

1 stop5h 47m

San Juan Luis Munoz Marin Intl

Mon 11/10

5:50 pm-11:00 pm

1 stop6h 10m

$341

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Thu 9/4

6:10 am-12:40 pm

1 stop6h 30m

Punta Cana

Mon 9/8

4:35 pm-11:44 pm

1 stop7h 09m

$431

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

2:02 pm-1:25 pm

2 stops22h 23m

San Juan Luis Munoz Marin Intl

Wed 12/10

2:30 pm-9:50 pm

1 stop8h 20m

$438

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Fri 8/15

9:32 am-12:20 pm

1 stop27h 48m

Montego Bay Sangster Intl

Fri 8/22

11:45 am-8:33 am

1 stop19h 48m

$438

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Mon 12/8

6:00 am-2:22 pm

1 stop7h 22m

Saint Thomas Island Cyril E King

Wed 12/10

3:32 pm-10:39 pm

1 stop8h 07m

$537

CharlottesvilleGregory Town

CHO - ELH

CHOELH

Charlottesville Albemarle

Tue 11/4

5:00 am-1:20 pm

2 stops8h 20m

Gregory Town North Eleuthera

Wed 11/5

2:50 pm-8:35 am

2 stops17h 45m

$590

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Wed 10/22

5:14 pm-3:10 pm

2 stops21h 56m

Simpson Bay Princess Juliana

Sun 10/26

4:25 pm-1:54 pm

2 stops21h 29m

$597

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 10/10

6:00 am-1:47 pm

1 stop7h 47m

Simpson Bay Princess Juliana

Wed 10/15

3:15 pm-10:39 pm

1 stop7h 24m

$600

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Thu 8/14

5:00 am-11:06 am

1 stop6h 06m

Saint Thomas Island Cyril E King

Thu 8/21

5:10 pm-2:27 pm

2 stops21h 17m

$615

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 22 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 July 3, 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 July 3, 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
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

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
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

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
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

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!
WestJet
7.2
Good
2,917 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

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.

  • 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 - Saint Thomas Island Cyril E King or Charlottesville Albemarle - Punta Cana 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$311Average$410FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$333Average$644FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$400Average$719FlexibilityNo cancel feeOn-time71%

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