$133 Find Cheap Flights from Charlottesville to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charlottesville to Caribbean Islands departing on 11/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Charlottesville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$434
Santo Domingo
Santo Domingo1 stop$516
Montego Bay
Montego Bay1 stop$424
Nassau
Nassau1 stop$362
Simpson Bay
Simpson Bay1 stop$375
George Town
George Town1 stop$357
Puerto Plata
Puerto Plata2 stops$855
Punta Cana
Punta Cana1 stop$434
Santo Domingo
Santo Domingo1 stop$516
Montego Bay
Montego Bay1 stop$424
Nassau
Nassau1 stop$362
Simpson Bay
Simpson Bay1 stop$375
George Town
George Town1 stop$357
Puerto Plata
Puerto Plata2 stops$855

Book Cheap Charlottesville to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Charlottesville to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Charlottesville to Caribbean Islands

Tue, Aug 25 - Mon, Aug 31
United Airlines Logo
6:45 am - 8:38 pm
CHO
-
SJU
13h 53m
2 stops
United Airlines Logo
1:00 am - 9:51 am
SJU
-
CHO
8h 51m
2 stops
$342United Airlines
Fri, Oct 30 - Wed, Nov 4
American Airlines Logo
6:08 pm - 11:20 am
CHO
-
SJU
17h 12m
1 stop
American Airlines Logo
6:28 am - 11:42 am
SJU
-
CHO
6h 14m
1 stop
$342American Airlines
Tue, Aug 25 - Tue, Sep 1
Delta Logo
6:00 am - 4:38 pm
CHO
-
SJU
10h 38m
1 stop
Delta Logo
2:59 pm - 11:35 pm
SJU
-
CHO
8h 36m
1 stop
$342Delta
Tue, Aug 25 - Tue, Sep 1
United Airlines Logo
6:45 am - 8:38 pm
CHO
-
SJU
13h 53m
2 stops
United Airlines Logo
4:55 pm - 11:44 pm
SJU
-
CHO
6h 49m
1 stop
$352United Airlines
Thu, Sep 10 - Thu, Sep 17
Delta Logo
6:00 am - 11:40 am
CHO
-
GCM
6h 40m
1 stop
Delta Logo
1:00 pm - 11:34 pm
GCM
-
CHO
9h 34m
1 stop
$357Delta
Sat, Nov 7 - Wed, Nov 11
American Airlines Logo
5:12 pm - 11:55 am
CHO
-
GCM
18h 43m
2 stops
American Airlines Logo
12:55 pm - 8:34 am
GCM
-
CHO
19h 39m
2 stops
$362American Airlines
Sat, Nov 7 - Wed, Nov 11
American Airlines Logo
7:17 pm - 11:23 am
CHO
-
GCM
16h 06m
1 stop
American Airlines Logo
3:45 pm - 10:32 am
GCM
-
CHO
18h 47m
2 stops
$362American Airlines
Thu, Jan 7 - Tue, Jan 12
United Airlines Logo
6:45 am - 3:22 pm
CHO
-
NAS
8h 37m
1 stop
United Airlines Logo
3:35 pm - 12:41 am
NAS
-
CHO
9h 06m
1 stop
$362United Airlines
Thu, Jan 7 - Tue, Jan 12
United Airlines Logo
6:45 am - 3:22 pm
CHO
-
NAS
8h 37m
1 stop
United Airlines Logo
4:25 pm - 1:26 pm
NAS
-
CHO
21h 01m
2 stops
$366United Airlines
Thu, Sep 10 - Thu, Sep 17
Delta Logo
6:00 am - 11:40 am
CHO
-
GCM
6h 40m
1 stop
Delta Logo
1:00 pm - 11:34 pm
GCM
-
CHO
9h 34m
1 stop
$411Delta
Booking Insights

KAYAK's insights & trends for Charlottesville to Caribbean Islands flights

Get data-powered insights and trends into flights from Charlottesville to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Charlottesville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $443, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Charlottesville to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charlottesville to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Charlottesville to Caribbean Islands is September, when tickets cost $368 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $2,500 and $1,227 respectively.

Good to know

Low season

April

Cheapest flight

$133
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 29% lower on average.
Flight from Charlottesville to Nassau

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Charlottesville to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Charlottesville to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Charlottesville to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Charlottesville to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Charlottesville to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Charlottesville to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Charlottesville to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Charlottesville to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Charlottesville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Charlottesville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Charlottesville to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10052 reviews
6.6Food
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

Airline tickets are not cheap. You expect reliable competent service. Thanks to canceled flights and botched transfers we arrived at our destination two days late. This is not acceptable

2.0 MediocreAnonymous, Jun 2026
ORF - EWR
Read more United Airlines reviews

Airline tickets are not cheap. You expect reliable competent service. Thanks to canceled flights and botched transfers we arrived at our destination two days late. This is not acceptable

We were a little disappointed to not be able to complete check in online without uploading pics of passports. Also we have KTN's and they weren't on our boarding passes when we got to security. Had to trek back to counter to have them fix.

They did the one thing that really matters - got to Chicago early.

The person I bought the ticket for didn’t make the flight.

Overall great. I was forced to check my carry-on backpack from EWR to BOS but it came out on the luggage carousel so fast I didn't even get delayed for my pickup.

Everything was perfect except the pad at the top of the seat back. It pushes my head forward into a very uncomfortable position and it is not removable.

The Check-in process at ORF for united is ABSOLUTELY TERRIBLE. I got there two hours early for a flight down the street and didn’t make it halfway to the register before I had to get out of line and remove my bags or miss my flight. This is every day thing and I’m clueless how this has gone on for years. This was the final straw. I’d rather pay a fortune more for a different airline than deal with this process

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

We waited to takeoff for about 1 hour delay for a 20 min flight.

Planes were on time, we were offered opportunities to take seats in exit aisles that had better leg room, tasks offs and landings were smooth, we were kept informed of flight status

Flight was delayed for 5 hours in ten minute increments. Bizarre and frustrating

Boarding was awful - no order, people cutting in line, completely chaotic Planes are very old and uncomfortable. Noticeable difference between Delta and United on same route.

They did not offer coffee on a 7am flight…awful!!

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

The flight took off an hour late which made the connection concerning

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

Never had such a lazy first class attendant. Literally spent 60%+ of the flight playing games on her personal phone making up excuses of why she was unavailable.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

No explanation of why there was no snack and drink service (unless requested) when there was service in the other direction.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports