$113 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 5/11. 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$560
Montego Bay
Montego Bay2 stops$357
Nassau
Nassau2 stops$376
Simpson Bay
Simpson Bay2 stops$590
George Town
George Town2 stops$352
Punta Cana
Punta Cana2 stops$373
Santo Domingo
Santo Domingo2 stops$560
Montego Bay
Montego Bay2 stops$357
Nassau
Nassau2 stops$376
Simpson Bay
Simpson Bay2 stops$590
George Town
George Town2 stops$352

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

seg, abr 13 - qua, abr 22
United Airlines Logo
6:40 am - 3:31 pm
CHO
-
STT
8h 51m
1 stop
United Airlines Logo
2:10 pm - 12:53 am
STT
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CHO
10h 43m
1 stop
$243United Airlines
ter, abr 14 - qua, abr 15
United Airlines Logo
6:20 am - 12:20 pm
CHO
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STT
6h 00m
1 stop
United Airlines Logo
2:10 pm - 12:53 am
STT
-
CHO
10h 43m
1 stop
$320United Airlines
ter, abr 28 - qui, abr 30
United Airlines Logo
6:20 am - 12:34 pm
CHO
-
SJU
6h 14m
1 stop
United Airlines Logo
1:00 am - 9:58 am
SJU
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CHO
8h 58m
2 stops
$327United Airlines
seg, mai 11 - seg, mai 18
American Airlines Logo
8:10 pm - 1:10 pm
CHO
-
GCM
18h 00m
2 stops
American Airlines Logo
12:00 pm - 9:54 am
GCM
-
CHO
20h 54m
2 stops
$352American Airlines
qui, mai 7 - dom, mai 10
American Airlines Logo
8:10 pm - 1:10 pm
CHO
-
GCM
18h 00m
2 stops
American Airlines Logo
12:00 pm - 8:39 am
GCM
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CHO
19h 39m
2 stops
$357American Airlines
sáb, mai 30 - sáb, jun 6
American Airlines Logo
6:09 pm - 1:08 pm
CHO
-
MBJ
19h 59m
2 stops
American Airlines Logo
2:08 pm - 8:33 am
MBJ
-
CHO
17h 25m
2 stops
$357American Airlines
seg, jun 29 - seg, jul 6
American Airlines Logo
6:09 pm - 11:04 am
CHO
-
PUJ
16h 55m
2 stops
American Airlines Logo
5:56 pm - 12:55 pm
PUJ
-
CHO
18h 59m
2 stops
$373American Airlines
qua, mai 6 - sáb, mai 9
Delta Logo
11:57 am - 8:26 pm
CHO
-
SJU
8h 29m
1 stop
Delta Logo
6:15 am - 3:36 pm
SJU
-
CHO
9h 21m
1 stop
$411Delta
sex, jun 19 - qua, jun 24
Delta Logo
6:00 am - 3:34 pm
CHO
-
MBJ
10h 34m
1 stop
Delta Logo
2:37 pm - 11:20 pm
MBJ
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CHO
7h 43m
1 stop
$714Delta
qua, ago 5 - dom, ago 9
Delta Logo
6:00 am - 1:17 pm
CHO
-
SDQ
7h 17m
1 stop
Delta Logo
2:42 pm - 11:22 pm
SDQ
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CHO
8h 40m
1 stop
$1,237Delta
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 ($243) and American Airlines ($352).

Good to know

Low seasonAugust
Cheapest flight$113
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 Saint Thomas Island

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 9499 reviews
7.1Entertainment
6.6Food
7.7Boarding
8.1Crew
7.3Comfort
Airline reviews

Overall, the flight was good. Lounge access should be with all business class tickets.

8.0 ExcellentIvan, Mar 2026
HNL - GUM
Read more United Airlines reviews

Overall, the flight was good. Lounge access should be with all business class tickets.

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Awful. No counter attendants. No dinner offered due to delays.

Horrible service no Wi-Fi connection on both leg of the flight and they are refusing to fix bad service

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

During landing. 2 crew members passed 3 times by my lane and didn't notice that people in front of us had their site to the furthermore reclined... That was uncomfortable and could have been dangerous.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

We had excellent customer service despite the chaos at George Bush airport in Houston!

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports