$126 Find Cheap Flights from Charlottesville to Caribbean

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 departing on 7/17. 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.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Charlottesville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$365
Santo Domingo
Santo Domingo2 stops$551
Montego Bay
Montego Bay2 stops$373
Nassau
Nassau2 stops$326
Simpson Bay
Simpson Bay1 stop$382
George Town
George Town2 stops$342
Puerto Plata
Puerto Plata2 stops$855
Punta Cana
Punta Cana2 stops$365
Santo Domingo
Santo Domingo2 stops$551
Montego Bay
Montego Bay2 stops$373
Nassau
Nassau2 stops$326
Simpson Bay
Simpson Bay1 stop$382
George Town
George Town2 stops$342
Puerto Plata
Puerto Plata2 stops$855

Book Cheap Charlottesville to Caribbean 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 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

Sat, Aug 15 - Wed, Aug 19
American Airlines Logo
5:16 pm - 9:30 am
CHO
-
NAS
16h 14m
2 stops
American Airlines Logo
7:45 am - 11:01 pm
NAS
-
CHO
15h 16m
2 stops
$326American Airlines
Sat, Aug 15 - Wed, Aug 19
American Airlines Logo
5:16 pm - 9:30 am
CHO
-
NAS
16h 14m
2 stops
American Airlines Logo
3:34 pm - 9:50 am
NAS
-
CHO
18h 16m
1 stop
$333American Airlines
Sat, Nov 7 - Wed, Nov 11
American Airlines Logo
5:00 am - 8:20 pm
CHO
-
GCM
15h 20m
2 stops
American Airlines Logo
1:00 pm - 8:30 am
GCM
-
CHO
19h 30m
2 stops
$342American Airlines
Sat, Nov 7 - Wed, Nov 11
American Airlines Logo
5:00 am - 8:20 pm
CHO
-
GCM
15h 20m
2 stops
American Airlines Logo
1:00 pm - 8:30 am
GCM
-
CHO
19h 30m
2 stops
$346American Airlines
Mon, Aug 17 - Wed, Aug 19
Delta Logo
2:32 pm - 11:51 am
CHO
-
NAS
21h 19m
2 stops
Delta Logo
1:16 pm - 11:11 pm
NAS
-
CHO
9h 55m
2 stops
$364Delta
Mon, Nov 2 - Thu, Nov 12
Delta Logo
6:00 am - 5:33 pm
CHO
-
SJU
10h 33m
1 stop
Delta Logo
7:00 am - 2:27 pm
SJU
-
CHO
8h 27m
1 stop
$365Delta
Wed, Oct 21 - Sun, Oct 25
United Airlines Logo
6:25 am - 12:34 pm
CHO
-
SJU
6h 09m
1 stop
United Airlines Logo
12:00 pm - 11:32 pm
SJU
-
CHO
11h 32m
2 stops
$396United Airlines
Mon, Nov 2 - Thu, Nov 12
United Airlines Logo
3:14 pm - 10:22 pm
CHO
-
SJU
6h 08m
1 stop
United Airlines Logo
8:05 am - 8:47 pm
SJU
-
CHO
13h 42m
2 stops
$440United Airlines
Fri, Jul 24 - Wed, Aug 5
Multiple Airlines Logo
2:56 pm - 5:00 pm
CHO
-
STT
26h 04m
1 stop
Multiple Airlines Logo
8:39 am - 11:43 pm
STT
-
CHO
15h 04m
2 stops
$1,023Multiple Airlines
Fri, Jul 24 - Wed, Aug 5
Multiple Airlines Logo
2:56 pm - 2:54 pm
CHO
-
STT
23h 58m
2 stops
Multiple Airlines Logo
10:49 am - 11:43 pm
STT
-
CHO
12h 54m
2 stops
$1,034Multiple Airlines
Booking Insights

KAYAK's insights & trends for Charlottesville to Caribbean flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charlottesville to Caribbean, 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 is February, when tickets cost $352 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is $684 and $576 respectively.

Good to know

Low seasonApril
Cheapest flight$126
Best time to beat the crowds but there is an average 42% increase in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from Charlottesville to Nassau

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Charlottesville to Caribbean 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?

    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 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?

    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 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

 
Need help choosing which airline to fly with from Charlottesville to Caribbean? 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 9893 reviews
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
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

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.

The flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

Pretty bad gate mgmt upon arrival. No open gates and we had to wait at midnight. Shouldn’t be a surprise that an aircraft is coming in.

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

Information on your arrival and departure airports