$247 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 7/5. 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$345
Montego Bay
Montego Bay1 stop$500
Nassau
Nassau1 stop$340
Simpson Bay
Simpson Bay1 stop$375
George Town
George Town2 stops$326
Puerto Plata
Puerto Plata2 stops$1,584
Punta Cana
Punta Cana2 stops$345
Montego Bay
Montego Bay1 stop$500
Nassau
Nassau1 stop$340
Simpson Bay
Simpson Bay1 stop$375
George Town
George Town2 stops$326
Puerto Plata
Puerto Plata2 stops$1,584

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, Nov 7 - Wed, Nov 11
American Airlines Logo
5:00 am - 8:20 pm
CHO
-
GCM
15h 20m
2 stops
American Airlines Logo
3:14 pm - 10:25 am
GCM
-
CHO
19h 11m
2 stops
$326American Airlines
Mon, Jun 8 - Mon, Jun 15
American Airlines Logo
8:00 pm - 10:02 am
CHO
-
NAS
14h 02m
1 stop
American Airlines Logo
12:39 pm - 11:54 pm
NAS
-
CHO
11h 15m
1 stop
$340American Airlines
Mon, Jun 8 - Mon, Jun 15
American Airlines Logo
8:00 pm - 9:27 am
CHO
-
NAS
13h 27m
2 stops
American Airlines Logo
12:39 pm - 11:54 pm
NAS
-
CHO
11h 15m
1 stop
$344American Airlines
Sat, Nov 14 - Wed, Nov 25
Delta Logo
5:40 pm - 3:40 pm
CHO
-
PUJ
21h 00m
2 stops
Delta Logo
5:05 pm - 10:38 am
PUJ
-
CHO
18h 33m
2 stops
$345Delta
Sat, Nov 14 - Sun, Nov 22
American Airlines Logo
6:03 pm - 11:55 am
CHO
-
PUJ
16h 52m
2 stops
American Airlines Logo
5:33 pm - 10:25 am
PUJ
-
CHO
17h 52m
2 stops
$350American Airlines
Sat, Nov 14 - Thu, Nov 19
Delta Logo
5:40 pm - 1:15 pm
CHO
-
PUJ
18h 35m
2 stops
Delta Logo
5:05 pm - 10:38 am
PUJ
-
CHO
18h 33m
2 stops
$415Delta
Thu, Jul 2 - Thu, Jul 9
United Airlines Logo
10:45 am - 1:47 pm
CHO
-
NAS
27h 02m
2 stops
United Airlines Logo
2:35 pm - 11:43 pm
NAS
-
CHO
33h 08m
2 stops
$460United Airlines
Tue, Oct 27 - Thu, Oct 29
United Airlines Logo
8:15 pm - 3:30 pm
CHO
-
GCM
20h 15m
2 stops
United Airlines Logo
4:45 pm - 9:26 am
GCM
-
CHO
39h 41m
2 stops
$461United Airlines
Fri, Nov 13 - Wed, Nov 25
Delta Logo
6:00 am - 3:40 pm
CHO
-
PUJ
8h 40m
1 stop
Delta Logo
3:50 pm - 10:38 am
PUJ
-
CHO
19h 48m
2 stops
$467Delta
Wed, Nov 11 - Wed, Nov 18
United Airlines Logo
6:30 am - 5:25 pm
CHO
-
PUJ
9h 55m
1 stop
United Airlines Logo
12:56 pm - 10:57 pm
PUJ
-
CHO
11h 01m
1 stop
$482United 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 $329 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $509 and $496 respectively.

Good to know

Low seasonAugust
Cheapest flight$247
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 27% lower on average.
Flight from Charlottesville to Punta Cana

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 9737 reviews
7.7Boarding
7.1Entertainment
8.1Crew
7.3Comfort
6.6Food
Airline reviews

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

6.0 Goodrsillman, May 2026
ACV - SFO
Read more United Airlines reviews

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

No complaints other than luggage carousel was incorrectly guiding passengers to the wrong carousel on the screen.

Did not like that we couldn't complete check in on-line without providing pictures of our passports. Worry about identity theft. We had no delays and boarding was handled In an efficient manner.

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.

Excellent service in Polaris class IAD to ZRH. Arrived rested and well fed after the overnight flight.

My flight time was changed without any notification to me which ruined my time sensitive plans so I ended up completely changing my travel plans and no reimbursement.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports