HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$236+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Charlottesville to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 24, 2025.

Round-trip from

$421
(American Airlines)

One-way from

$236
(American Airlines)

Popular in

July

Cheapest in

March

Average price

$555
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. 11% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 April 24, 2025.

This American Airlines deal was found by Cheapflights users on 4/23. 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.
Fri 5/95:05 amCHO - SJU
1 stop6h 05mAmerican Airlines
Tue 5/137:15 amSJU - CHO
1 stop16h 43mAmerican Airlines
Deal found 4/23$421
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 11/45:00 amCHO - STT
1 stop9h 48mAmerican Airlines
Tue 11/116:15 pmSTT - CHO
2 stops20h 11mAmerican Airlines
Deal found 4/23$439
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 6/38:24 pmCHO - SDQ
2 stops14h 51mAmerican Airlines
Thu 6/197:00 amSDQ - CHO
2 stops17h 12mAmerican Airlines
Deal found 4/23$445
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/36:10 amCHO - MBJ
1 stop10h 00mUnited Airlines
Thu 8/74:12 pmMBJ - CHO
1 stop6h 18mUnited Airlines
Deal found 4/23$445
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 7/246:06 pmCHO - MBJ
2 stops16h 24mAmerican Airlines
Mon 7/282:25 pmMBJ - CHO
2 stops17h 03mAmerican Airlines
Deal found 4/23$512
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2310:45 amCHO - SJU
2 stops13h 09mUnited Airlines
Wed 6/251:05 amSJU - CHO
2 stops8h 29mUnited Airlines
Deal found 4/23$520
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:00 amCHO - STT
1 stop7h 32mDelta
Wed 10/222:42 pmSTT - CHO
1 stop7h 57mDelta
Deal found 4/23$543
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/610:45 amCHO - NAS
2 stops29h 13mUnited Airlines
Fri 6/132:33 pmNAS - CHO
2 stops23h 17mUnited Airlines
Deal found 4/23$569
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sun 6/85:00 amCHO - SXM
2 stops10h 05mAmerican Airlines
Sun 6/154:05 pmSXM - CHO
2 stops25h 39mAmerican Airlines
Deal found 4/23$572
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/36:10 amCHO - STT
1 stop6h 07mUnited Airlines
Mon 7/74:45 pmSTT - CHO
1 stop6h 45mUnited Airlines
Deal found 4/23$598
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/86:10 amCHO - SXM
1 stop6h 19mUnited Airlines
Sun 6/153:55 pmSXM - CHO
2 stops18h 30mUnited Airlines
Deal found 4/23$604
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/267:00 amCHO - GCM
1 stop5h 22mDelta
Sat 5/101:03 pmGCM - CHO
1 stop9h 31mDelta
Deal found 4/23$605

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 April 24, 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

Fri 5/9

5:05 am-11:10 am

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Tue 5/13

7:15 am-11:58 pm

1 stop16h 43m

$421

CharlottesvilleSanto Domingo

CHO - SDQ

CHOSDQ

Charlottesville Albemarle

Tue 6/3

8:24 pm-11:15 am

2 stops14h 51m

Santo Domingo Las Americas

Thu 6/19

7:00 am-12:12 am

2 stops17h 12m

$445

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 6/23

10:45 am-11:54 pm

2 stops13h 09m

San Juan Luis Munoz Marin Intl

Wed 6/25

1:05 am-9:34 am

2 stops8h 29m

$520

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Tue 10/14

6:00 am-1:32 pm

1 stop7h 32m

Saint Thomas Island Cyril E King

Wed 10/22

2:42 pm-10:39 pm

1 stop7h 57m

$543

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Fri 6/6

10:45 am-3:58 pm

2 stops29h 13m

Nassau Intl

Fri 6/13

2:33 pm-1:50 pm

2 stops23h 17m

$569

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 6/8

5:00 am-3:05 pm

2 stops10h 05m

Simpson Bay Princess Juliana

Sun 6/15

4:05 pm-5:44 pm

2 stops25h 39m

$572

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Thu 7/3

6:10 am-12:17 pm

1 stop6h 07m

Saint Thomas Island Cyril E King

Mon 7/7

4:45 pm-11:30 pm

1 stop6h 45m

$598

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 6/8

6:10 am-12:29 pm

1 stop6h 19m

Simpson Bay Princess Juliana

Sun 6/15

3:55 pm-10:25 am

2 stops18h 30m

$604

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Thu 7/3

5:50 am-11:59 am

1 stop6h 09m

San Juan Luis Munoz Marin Intl

Mon 7/7

6:15 am-4:51 pm

1 stop10h 36m

$623

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Tue 10/14

6:30 am-11:50 am

2 stops29h 20m

Saint Thomas Island Cyril E King

Wed 10/22

10:55 am-11:00 pm

2 stops12h 05m

$673

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 17 results
1
2

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, September is the cheapest month in which you can book a flight from Charlottesville to Caribbean Islands (average of $254). Flying from Charlottesville to Caribbean Islands in December is currently the most expensive (average of $336). 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 April 24, 2025.

When flying from Charlottesville to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 24, 2025.
To help decide which airline to fly from Charlottesville to Caribbean Islands, see what other customers have to say about Delta, 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.
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    While some choose either Charlottesville Albemarle - Montego Bay Sangster Intl or Charlottesville Albemarle - San Juan Luis Munoz Marin Intl, Charlottesville Albemarle - Saint Thomas Island Cyril E King 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, September is the cheapest month in which you can book a flight from Charlottesville to Caribbean Islands (average of $254). Flying from Charlottesville to Caribbean Islands in December is currently the most expensive (average of $336). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Charlottesville to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Los Angeles flights
Reagan-National to Los Angeles flights
Dulles Intl to Las Vegas flights
Dulles Intl to Cancún flights
Reagan-National to Seattle flights
Dulles Intl to Seattle flights
Reagan-National to Las Vegas flights
Dulles Intl to San Francisco flights
Dulles Intl to Dallas/Fort Worth flights
Reagan-National to San Francisco flights
Reagan-National to O'Hare Intl flights
Dulles Intl to Miami flights
Reagan-National to Dallas/Fort Worth flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Hobby flights
Reagan-National to Miami flights
Reagan-National to Boston flights
Reagan-National to Atlanta flights
Dulles Intl to Orlando flights
Dulles Intl to Tampa flights
Dulles Intl to Atlanta flights
Dulles Intl to Boston flights
Raleigh to O'Hare Intl flights
Raleigh to John F Kennedy Intl flights
Reagan-National to Orlando flights
Reagan-National to Hobby flights
Reagan-National to Cancún flights
Dulles Intl to Mexico City flights
Dulles Intl to Denver flights
Raleigh to Seattle flights
Dulles Intl to Midway flights
Dulles Intl to George Bush Intcntl flights
Reagan-National to Denver flights
Dulles Intl to Sky Harbor Intl flights
Raleigh to Las Vegas flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to New Orleans flights
Raleigh to LaGuardia flights
Raleigh to Newark flights
Dulles Intl to San Diego flights
Raleigh to Miami flights
Reagan-National to Nashville flights
Reagan-National to San Diego flights
Reagan-National to Tampa flights
Raleigh to Denver flights
Reagan-National to Sky Harbor Intl flights
Dulles Intl to Austin flights
Reagan-National to George Bush Intcntl flights
Reagan-National to New Orleans flights
Dulles Intl to Honolulu flights

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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$311Average$410FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$333Average$601FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$397Average$701FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.