$116 Find Cheap Flights from Charlottesville to Caribbean Islands

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 Islands departing on 1/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charlottesville to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charlottesville to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Charlottesville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$306
Santo Domingo
Santo Domingo2 stops$318
Montego Bay
Montego Bay1 stop$331
Nassau
Nassau1 stop$350
Simpson Bay
Simpson Bay2 stops$298
George Town
George Town1 stop$296
Puerto Plata
Puerto Plata1 stop$444
Punta Cana
Punta Cana2 stops$306
Santo Domingo
Santo Domingo2 stops$318
Montego Bay
Montego Bay1 stop$331
Nassau
Nassau1 stop$350
Simpson Bay
Simpson Bay2 stops$298
George Town
George Town1 stop$296
Puerto Plata
Puerto Plata1 stop$444

Book Cheap Charlottesville to Caribbean Islands 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 Islands 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 Islands

Wed, Jan 7 - Wed, Jan 14
American Airlines Logo
7:09 pm - 11:26 am
CHO
-
GCM
16h 17m1 stop
American Airlines Logo
12:16 pm - 8:55 pm
GCM
-
CHO
8h 39m1 stop
$296American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
5:20 pm - 4:28 pm
CHO
-
SXM
22h 08m2 stops
American Airlines Logo
5:33 pm - 11:58 am
SXM
-
CHO
19h 25m2 stops
$298American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
6:00 am - 1:45 pm
CHO
-
SXM
6h 45m1 stop
American Airlines Logo
5:01 pm - 9:59 am
SXM
-
CHO
17h 58m1 stop
$299American Airlines
Wed, Jan 7 - Wed, Jan 14
American Airlines Logo
7:09 pm - 11:26 am
CHO
-
GCM
16h 17m1 stop
American Airlines Logo
1:05 pm - 9:59 am
GCM
-
CHO
20h 54m2 stops
$301American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
5:20 pm - 1:45 pm
CHO
-
SXM
19h 25m1 stop
American Airlines Logo
5:33 pm - 9:59 am
SXM
-
CHO
17h 26m2 stops
$304American Airlines
Sat, Jan 17 - Wed, Jan 21
United Airlines Logo
8:15 am - 10:22 pm
CHO
-
SJU
13h 07m2 stops
United Airlines Logo
8:35 am - 7:44 pm
SJU
-
CHO
12h 09m2 stops
$362United Airlines
Thu, Mar 5 - Wed, Mar 11
Delta Logo
7:00 am - 5:02 pm
CHO
-
NAS
10h 02m2 stops
Delta Logo
6:10 pm - 1:35 pm
NAS
-
CHO
19h 25m2 stops
$367Delta
Sun, Apr 19 - Wed, Apr 22
United Airlines Logo
6:30 am - 4:30 pm
CHO
-
PUJ
10h 00m1 stop
United Airlines Logo
4:40 pm - 9:26 am
PUJ
-
CHO
16h 46m1 stop
$400United Airlines
Thu, Mar 5 - Thu, Mar 12
Delta Logo
7:00 am - 5:02 pm
CHO
-
NAS
10h 02m2 stops
Delta Logo
3:40 pm - 10:37 pm
NAS
-
CHO
6h 57m1 stop
$405Delta
Sat, Jan 10 - Wed, Jan 14
WestJet Logo
6:00 am - 9:37 am
CHO
-
POP
26h 37m2 stops
WestJet Logo
5:30 pm - 10:39 pm
POP
-
CHO
30h 09m2 stops
$1,496WestJet
Booking Insights

KAYAK's insights & trends for Charlottesville to Caribbean Islands flights

Get data-powered insights and trends into flights from Charlottesville to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Charlottesville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $423, prices are generally cheapest when you fly direct.

Good to know

Low seasonAugust
Cheapest flight$116
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Charlottesville to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Charlottesville to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Charlottesville to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Charlottesville to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $568 on average. Morning departures are around 20% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $714.

Reviews of the top airlines flying from Charlottesville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Charlottesville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Charlottesville to Caribbean Islands? 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 9094 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

United have really come back. Airport and boarding process is clear and good, app and information also very good

They charged a fee for 1st bag checked. Others in same party were free.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Not comparable to Qatar Airways services on flights to Doha. Flight attendants provided basic services; I was never recognized by name or as an Executive Platinum member. Restrooms were not kept clean during the flight.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports