$98 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 3/8. 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
Montego Bay
Montego Bay1 stop$349
Nassau
Nassau2 stops$328
Simpson Bay
Simpson Bay1 stop$290
George Town
George Town2 stops$302
Puerto Plata
Puerto Plata2 stops$519
Punta Cana
Punta Cana1 stop$319
Montego Bay
Montego Bay1 stop$349
Nassau
Nassau2 stops$328
Simpson Bay
Simpson Bay1 stop$290
George Town
George Town2 stops$302
Puerto Plata
Puerto Plata2 stops$519

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

Sun, Feb 22 - Thu, Feb 26
American Airlines Logo
7:57 pm - 1:53 pm
CHO
-
SJU
16h 56m
1 stop
American Airlines Logo
5:18 pm - 8:27 am
SJU
-
CHO
16h 09m
1 stop
$232American Airlines
Mon, Mar 23 - Mon, Mar 30
United Airlines Logo
8:29 pm - 12:50 pm
CHO
-
SXM
16h 21m
1 stop
United Airlines Logo
3:50 pm - 10:10 am
SXM
-
CHO
18h 20m
2 stops
$290United Airlines
Tue, Mar 24 - Tue, Mar 31
United Airlines Logo
6:20 am - 12:50 pm
CHO
-
SXM
6h 30m
1 stop
United Airlines Logo
3:50 pm - 9:58 am
SXM
-
CHO
18h 08m
1 stop
$291United Airlines
Thu, Feb 26 - Wed, Mar 4
American Airlines Logo
7:57 pm - 12:05 pm
CHO
-
GCM
16h 08m
2 stops
American Airlines Logo
3:45 pm - 8:27 am
GCM
-
CHO
16h 42m
2 stops
$302American Airlines
Tue, Mar 24 - Tue, Mar 31
United Airlines Logo
6:20 am - 12:50 pm
CHO
-
SXM
6h 30m
1 stop
United Airlines Logo
3:50 pm - 10:10 am
SXM
-
CHO
18h 20m
2 stops
$313United Airlines
Thu, Feb 26 - Thu, Mar 5
American Airlines Logo
7:57 pm - 2:19 pm
CHO
-
SXM
17h 22m
2 stops
American Airlines Logo
1:29 pm - 8:27 am
SXM
-
CHO
19h 58m
2 stops
$316American 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
Fri, Feb 6 - Sun, Feb 8
JetBlue Logo
6:00 am - 2:31 pm
CHO
-
SJU
7h 31m
1 stop
JetBlue Logo
2:15 pm - 10:51 pm
SJU
-
CHO
9h 36m
1 stop
$352JetBlue
Wed, Mar 11 - Tue, Mar 17
Delta Logo
2:27 pm - 11:12 pm
CHO
-
SJU
8h 45m
1 stop
Delta Logo
6:15 am - 5:10 pm
SJU
-
CHO
10h 55m
1 stop
$396Delta
Thu, Mar 19 - Sun, Mar 22
Delta Logo
6:00 am - 2:38 pm
CHO
-
POP
8h 38m
1 stop
Delta Logo
3:55 pm - 10:48 pm
POP
-
CHO
6h 53m
1 stop
$2,338Delta
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 ($232) and United Airlines ($290).

Good to know

Low seasonAugust
Cheapest flight$98
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Charlottesville to Simpson Bay

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 9174 reviews
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
8.1Crew
Airline reviews

The flight crew where really good. Better then the crew from BNE to SFO

10.0 ExcellentVanessa, Jan 2026
SFO - IAD
Read more United Airlines reviews

The flight crew where really good. Better then the crew from BNE to SFO

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

My seat tv didn’t work the whole trip. And the seat space is too small despite being seated at the front.

The seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports