$110 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 3/11. 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 Cana1 stop$333
Santo Domingo
Santo Domingo2 stops$746
Montego Bay
Montego Bay2 stops$317
Nassau
Nassau1 stop$343
Simpson Bay
Simpson Bay2 stops$350
George Town
George Town1 stop$563
Puerto Plata
Puerto Plata2 stops$676
Punta Cana
Punta Cana1 stop$333
Santo Domingo
Santo Domingo2 stops$746
Montego Bay
Montego Bay2 stops$317
Nassau
Nassau1 stop$343
Simpson Bay
Simpson Bay2 stops$350
George Town
George Town1 stop$563
Puerto Plata
Puerto Plata2 stops$676

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

Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
7:13 pm - 11:51 am
CHO
-
MBJ
17h 38m
2 stops
American Airlines Logo
12:56 pm - 8:39 am
MBJ
-
CHO
18h 43m
2 stops
$317American 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 10 - Tue, Mar 17
Delta Logo
6:00 am - 4:18 pm
CHO
-
SJU
10h 18m
1 stop
Delta Logo
1:00 pm - 10:48 pm
SJU
-
CHO
9h 48m
1 stop
$329Delta
Mon, Apr 20 - Thu, Apr 23
American Airlines Logo
5:05 am - 12:39 pm
CHO
-
PUJ
7h 34m
1 stop
American Airlines Logo
2:30 pm - 8:39 am
PUJ
-
CHO
18h 09m
2 stops
$333American Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
8:00 pm - 11:38 am
CHO
-
NAS
15h 38m
1 stop
American Airlines Logo
2:18 pm - 8:33 am
NAS
-
CHO
18h 15m
1 stop
$343American Airlines
Tue, May 5 - Sun, May 10
American Airlines Logo
10:19 am - 8:51 pm
CHO
-
SJU
10h 32m
1 stop
American Airlines Logo
4:30 pm - 11:54 pm
SJU
-
CHO
7h 24m
1 stop
$347American Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
8:00 pm - 9:27 am
CHO
-
NAS
13h 27m
2 stops
American Airlines Logo
2:18 pm - 8:33 am
NAS
-
CHO
18h 15m
1 stop
$347American 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
Wed, May 27 - Tue, Jun 2
United Airlines Logo
5:45 pm - 5:29 am
CHO
-
SJU
11h 44m
2 stops
United Airlines Logo
1:00 am - 9:26 am
SJU
-
CHO
8h 26m
2 stops
$359United 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 ($317) and Delta ($322).

Good to know

Low seasonAugust
Cheapest flight$110
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 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 9279 reviews
8.1Crew
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

Short flight, but no drink/snack service. The flights both going and coming were delayed.

6.0 GoodDaymond, Feb 2026
ORD - SDF
Read more United Airlines reviews

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Much better than Spirit. I was please by the easy fast check in and boarding

Check-in and in-flight staff were better than average. The seat was a fair size but too hard and not enough padding. The cushion/pillow provided is poor (thin and seems to be disposable ,it provides no effective cushioning or support). Food was OK-ish but no choice of inflight snacks and no easy place to get drinks other than water (I could ask for juice by intruding into the staff area at the back of the plane) Entertainment was very good actually. Overall better than I expected from a US-based airline (sorry!) but compared to ANA or Singapore it was so-so. (I live in Japan so they are my comparative airlines)

Everything was on time Will use united again for sure

Plane outlets in my row not working to charge phone. Staff response was, well it should be. Plug into seed for volume not working well. Had to find the sweet spot for plug in or it would shut off and on.

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.

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports