$235 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 7/5. 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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Flight Deals

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$359
Montego Bay
Montego Bay2 stops$479
Nassau
Nassau1 stop$340
Simpson Bay
Simpson Bay2 stops$496
George Town
George Town1 stop$326
Punta Cana
Punta Cana1 stop$359
Montego Bay
Montego Bay2 stops$479
Nassau
Nassau1 stop$340
Simpson Bay
Simpson Bay2 stops$496
George Town
George Town1 stop$326

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, Jun 1 - Sat, Jun 13
American Airlines Logo
8:00 pm - 11:30 am
CHO
-
GCM
16h 30m
1 stop
American Airlines Logo
12:40 pm - 8:33 am
GCM
-
CHO
18h 53m
2 stops
$326American Airlines
Mon, Jun 8 - Wed, Jun 10
American Airlines Logo
8:00 pm - 10:02 am
CHO
-
NAS
14h 02m
1 stop
American Airlines Logo
11:02 am - 11:54 pm
NAS
-
CHO
12h 52m
1 stop
$340American 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
12:47 pm - 10:13 pm
NAS
-
CHO
9h 26m
2 stops
$344American Airlines
Mon, Jun 8 - Thu, Jun 11
American Airlines Logo
8:00 pm - 10:02 am
CHO
-
NAS
14h 02m
1 stop
American Airlines Logo
12:39 pm - 8:33 am
NAS
-
CHO
19h 54m
1 stop
$347American Airlines
Mon, Jul 6 - Fri, Jul 10
United Airlines Logo
6:30 am - 2:27 pm
CHO
-
PUJ
7h 57m
1 stop
United Airlines Logo
1:50 pm - 9:56 am
PUJ
-
CHO
20h 06m
1 stop
$359United Airlines
Tue, Nov 3 - Mon, Nov 9
Delta Logo
11:50 am - 10:59 pm
CHO
-
SJU
10h 09m
1 stop
Delta Logo
3:35 pm - 10:49 pm
SJU
-
CHO
8h 14m
1 stop
$385Delta
Sat, Oct 24 - Wed, Oct 28
United Airlines Logo
7:45 pm - 1:33 pm
CHO
-
NAS
17h 48m
2 stops
United Airlines Logo
2:55 pm - 10:11 am
NAS
-
CHO
19h 16m
2 stops
$430United Airlines
Tue, Nov 3 - Mon, Nov 9
United Airlines Logo
8:35 am - 10:22 pm
CHO
-
SJU
12h 47m
2 stops
United Airlines Logo
5:50 pm - 10:57 pm
SJU
-
CHO
6h 07m
1 stop
$439United Airlines
Sat, Sep 19 - Thu, Sep 24
Delta Logo
11:50 am - 10:00 pm
CHO
-
SJU
10h 10m
1 stop
Delta Logo
12:58 pm - 10:49 pm
SJU
-
CHO
9h 51m
1 stop
$568Delta
Sat, Jul 4 - Mon, Jul 6
Delta Logo
7:00 am - 4:46 pm
CHO
-
SJU
9h 46m
1 stop
Delta Logo
12:54 pm - 11:13 pm
SJU
-
CHO
10h 19m
1 stop
$576Delta
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.

What is the cheapest month to fly from Charlottesville to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charlottesville to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Charlottesville to Caribbean is February, when tickets cost $329 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $509 and $496 respectively.

Good to know

Low seasonAugust
Cheapest flight$235
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 27% lower on average.
Flight from Charlottesville to Punta Cana

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 9723 reviews
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

10.0 ExcellentAnonymous, May 2026
IAD - MUC
Read more United Airlines reviews

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports