$176 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 8/22. 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.
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$373
Santo Domingo
Santo Domingo2 stops$369
Montego Bay
Montego Bay1 stop$357
Nassau
Nassau2 stops$376
Simpson Bay
Simpson Bay1 stop$390
George Town
George Town1 stop$920
Puerto Plata
Puerto Plata2 stops$658
Punta Cana
Punta Cana2 stops$373
Santo Domingo
Santo Domingo2 stops$369
Montego Bay
Montego Bay1 stop$357
Nassau
Nassau2 stops$376
Simpson Bay
Simpson Bay1 stop$390
George Town
George Town1 stop$920
Puerto Plata
Puerto Plata2 stops$658

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

Mon, Apr 27 - Wed, Apr 29
United Airlines Logo
6:20 am - 12:20 pm
CHO
-
STT
6h 00m
1 stop
United Airlines Logo
2:10 pm - 12:53 am
STT
-
CHO
10h 43m
1 stop
$241United Airlines
Tue, Apr 7 - Thu, Apr 16
United Airlines Logo
6:20 am - 12:20 pm
CHO
-
STT
6h 00m
1 stop
United Airlines Logo
2:10 pm - 12:53 am
STT
-
CHO
10h 43m
1 stop
$276United Airlines
Tue, Apr 28 - Tue, Apr 28
United Airlines Logo
6:20 am - 8:34 pm
CHO
-
SJU
14h 14m
2 stops
United Airlines Logo
1:00 am - 9:58 am
SJU
-
CHO
8h 58m
2 stops
$317United Airlines
Fri, Aug 14 - Sat, Aug 22
American Airlines Logo
6:49 am - 10:56 pm
CHO
-
SJU
16h 07m
1 stop
American Airlines Logo
3:50 pm - 8:28 am
SJU
-
CHO
16h 38m
1 stop
$332American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
8:03 pm - 9:13 am
CHO
-
MBJ
14h 10m
1 stop
American Airlines Logo
12:56 pm - 8:39 am
MBJ
-
CHO
18h 43m
2 stops
$357American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
8:03 pm - 9:13 am
CHO
-
MBJ
14h 10m
1 stop
American Airlines Logo
2:29 pm - 8:39 am
MBJ
-
CHO
17h 10m
1 stop
$358American Airlines
Wed, May 20 - Mon, May 25
American Airlines Logo
6:07 pm - 11:45 am
CHO
-
MBJ
18h 38m
2 stops
American Airlines Logo
5:17 pm - 12:54 pm
MBJ
-
CHO
18h 37m
2 stops
$362American Airlines
Sat, May 16 - Wed, May 20
Delta Logo
7:00 am - 1:10 pm
CHO
-
NAS
6h 10m
1 stop
Delta Logo
6:00 pm - 11:44 pm
NAS
-
CHO
5h 44m
1 stop
$416Delta
Fri, Apr 17 - Fri, Apr 24
Delta Logo
6:00 am - 1:12 pm
CHO
-
SDQ
7h 12m
1 stop
Delta Logo
2:37 pm - 10:55 pm
SDQ
-
CHO
8h 18m
1 stop
$933Delta
Mon, Aug 3 - Mon, Aug 10
Delta Logo
6:00 am - 1:26 pm
CHO
-
SDQ
7h 26m
1 stop
Delta Logo
2:37 pm - 10:49 pm
SDQ
-
CHO
8h 12m
1 stop
$1,291Delta
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.

Which airlines provide the cheapest flights from Charlottesville to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Charlottesville to Caribbean were found on United Airlines ($241) and American Airlines ($369).

Good to know

Low seasonAugust
Cheapest flight$176
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Charlottesville to Santo Domingo

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 9431 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

10.0 ExcellentAnonymous, Mar 2026
TPA - IAD
Read more United Airlines reviews

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports