$116 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 3/2. 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 Cana1 stop$319
Santo Domingo
Santo Domingo2 stops$641
Montego Bay
Montego Bay2 stops$317
Nassau
Nassau2 stops$330
Simpson Bay
Simpson Bay2 stops$426
George Town
George Town2 stops$302
Puerto Plata
Puerto Plata2 stops$556
Punta Cana
Punta Cana1 stop$319
Santo Domingo
Santo Domingo2 stops$641
Montego Bay
Montego Bay2 stops$317
Nassau
Nassau2 stops$330
Simpson Bay
Simpson Bay2 stops$426
George Town
George Town2 stops$302
Puerto Plata
Puerto Plata2 stops$556

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, Mar 9 - Tue, Mar 17
Delta Logo
11:54 am - 8:18 pm
CHO
-
SJU
8h 24m
1 stop
Delta Logo
1:00 pm - 10:48 pm
SJU
-
CHO
9h 48m
1 stop
$234Delta
Mon, Feb 23 - Thu, Feb 26
American Airlines Logo
5:00 pm - 12:12 pm
CHO
-
STT
18h 12m
2 stops
American Airlines Logo
5:42 pm - 8:27 am
STT
-
CHO
15h 45m
1 stop
$286American Airlines
Sun, Mar 8 - Thu, Mar 12
American Airlines Logo
7:57 pm - 11:05 am
CHO
-
GCM
16h 08m
2 stops
American Airlines Logo
11:40 am - 8:27 am
GCM
-
CHO
19h 47m
2 stops
$302American Airlines
Tue, Mar 24 - Tue, Mar 31
American Airlines Logo
7:17 pm - 11:10 am
CHO
-
GCM
16h 53m
1 stop
American Airlines Logo
3:15 pm - 1:12 pm
GCM
-
CHO
20h 57m
2 stops
$308American Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
7:13 pm - 12:13 pm
CHO
-
MBJ
18h 00m
2 stops
American Airlines Logo
12:56 pm - 8:39 am
MBJ
-
CHO
18h 43m
2 stops
$317American Airlines
Sat, Feb 21 - Tue, Mar 3
American Airlines Logo
7:57 pm - 11:34 am
CHO
-
PUJ
14h 37m
1 stop
American Airlines Logo
5:41 pm - 9:47 am
PUJ
-
CHO
17h 06m
1 stop
$319American Airlines
Mon, Feb 23 - Thu, Feb 26
Delta Logo
6:00 am - 5:27 pm
CHO
-
SJU
10h 27m
1 stop
Delta Logo
6:15 am - 1:46 pm
SJU
-
CHO
8h 31m
1 stop
$322Delta
Tue, Mar 24 - Tue, Mar 31
United Airlines Logo
6:45 am - 12:45 pm
CHO
-
GCM
7h 00m
1 stop
United Airlines Logo
1:50 pm - 12:36 am
GCM
-
CHO
9h 46m
1 stop
$341United Airlines
Tue, Mar 10 - Tue, Mar 17
United Airlines Logo
10:45 am - 11:36 pm
CHO
-
SJU
12h 51m
2 stops
United Airlines Logo
7:05 am - 1:59 pm
SJU
-
CHO
6h 54m
1 stop
$349United Airlines
Mon, Mar 9 - Mon, Mar 16
WestJet Logo
11:54 am - 3:27 pm
CHO
-
POP
27h 33m
2 stops
WestJet Logo
4:30 pm - 10:37 pm
POP
-
CHO
30h 07m
2 stops
$3,713WestJet
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 American Airlines ($286) and United Airlines ($322).

Good to know

Low seasonAugust
Cheapest flight$116
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Charlottesville to San Juan

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 9259 reviews
7.1Entertainment
8.1Crew
6.6Food
7.7Boarding
7.3Comfort
Airline reviews

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

6.0 Goodrob, Feb 2026
IAD - YYZ
Read more United Airlines reviews

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Fine not above and beyond as I had a connection that was delayed due to maintenance

The power at the seat didn't work and the seat itself was difficult to adjust - this was a business class seat. Flight attendant gave me miles to compensate. The attendant was very professional and on top of his game the entire flight.

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

I upgraded my seat and was promised it would be next to the emergency door for extra leg room and they said it was premium plus but it was at the back of the plane...same thing happened from Newark to Dubai

Everything except the food and entertainment. It was a great experience though

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

Flight was on time and the meal and service were good.

The accessible bathroom should be visible to people in Economy class.

Flight was delayed for 2 hours, then last minute the change to on time. The satélite location is far and a nightmare to get to.

This was a horrible experience. I’ve experienced several delays at this point and still not home. I was supposed to be home by 8:30 last night and here I sit at 7 am on a plane STILL unable to go home because of American Airlines.

Lexus in first class was absolutely amazing! Beat flight attendant i’ve ever seen.

Generally good. Flight left on time and the seats are comfortable. Plenty of space in front if you in you choose a comfort plus seat, completely worth spending the extra money given the amount of hours the flight lasts. The food tastes good but I would say it’s a the amount is too little. The crew was friendly and efficient. There was a some turbulence at different points into the flight. American Airlines has good deals to NZ if you book with plenty of time before you plan on going.

the plane was so hot!! the air-conditioning was barely blowing. The flight was delayed, and we had to sit on the hot plane before take off for an extended amount of time, waiting on international passengers. Would not have been so bad if it was not so hot. They said it would get better after take off, but it did not.

They are always late and seats was also not having working charger

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports