$250 Find Cheap Flights from Charlottesville to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charlottesville to Caribbean departing on 8/29. 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 Cana2 stops$410
Santo Domingo
Santo Domingo2 stops$576
Montego Bay
Montego Bay1 stop$838
Nassau
Nassau1 stop$558
Simpson Bay
Simpson Bay2 stops$362
George Town
George Town2 stops$326
Puerto Plata
Puerto Plata2 stops$1,079
Punta Cana
Punta Cana2 stops$410
Santo Domingo
Santo Domingo2 stops$576
Montego Bay
Montego Bay1 stop$838
Nassau
Nassau1 stop$558
Simpson Bay
Simpson Bay2 stops$362
George Town
George Town2 stops$326
Puerto Plata
Puerto Plata2 stops$1,079

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

Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
6:25 am - 12:58 pm
CHO
-
STT
6h 33m
1 stop
United Airlines Logo
4:45 pm - 11:44 pm
STT
-
CHO
6h 59m
1 stop
$250United Airlines
Sat, Nov 7 - Wed, Nov 11
American Airlines Logo
6:03 pm - 11:58 am
CHO
-
GCM
17h 55m
2 stops
American Airlines Logo
1:00 pm - 8:30 am
GCM
-
CHO
19h 30m
2 stops
$326American Airlines
Mon, Jun 22 - Fri, Jun 26
American Airlines Logo
8:00 pm - 3:42 pm
CHO
-
SXM
19h 42m
2 stops
American Airlines Logo
1:40 pm - 8:33 am
SXM
-
CHO
18h 53m
2 stops
$362American Airlines
Sat, Sep 12 - Tue, Sep 22
American Airlines Logo
7:11 pm - 11:30 am
CHO
-
GCM
17h 19m
1 stop
American Airlines Logo
12:00 pm - 11:51 am
GCM
-
CHO
22h 51m
2 stops
$409American Airlines
Sat, Nov 14 - Sun, Nov 22
American Airlines Logo
6:03 pm - 11:55 am
CHO
-
PUJ
16h 52m
2 stops
American Airlines Logo
5:33 pm - 10:25 am
PUJ
-
CHO
17h 52m
2 stops
$410American Airlines
Wed, Sep 16 - Tue, Sep 22
American Airlines Logo
7:11 pm - 11:30 am
CHO
-
GCM
17h 19m
1 stop
American Airlines Logo
12:00 pm - 11:51 am
GCM
-
CHO
22h 51m
2 stops
$414American Airlines
Tue, Sep 15 - Tue, Sep 22
American Airlines Logo
2:01 pm - 11:27 am
CHO
-
GCM
22h 26m
2 stops
American Airlines Logo
12:00 pm - 11:51 am
GCM
-
CHO
22h 51m
2 stops
$416American Airlines
Sat, Nov 7 - Wed, Nov 11
United Airlines Logo
6:30 am - 4:35 pm
CHO
-
GCM
10h 05m
1 stop
United Airlines Logo
5:45 pm - 10:11 am
GCM
-
CHO
16h 26m
2 stops
$446United Airlines
Tue, Jun 30 - Wed, Jul 1
Delta Logo
6:00 am - 1:25 pm
CHO
-
PUJ
7h 25m
1 stop
Delta Logo
4:00 pm - 11:13 pm
PUJ
-
CHO
7h 13m
1 stop
$549Delta
Tue, Jun 30 - Mon, Jul 6
Delta Logo
6:00 am - 2:35 pm
CHO
-
PUJ
8h 35m
1 stop
Delta Logo
2:50 pm - 2:00 pm
PUJ
-
CHO
23h 10m
2 stops
$554Delta
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 November, when tickets cost $261 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $545 and $538 respectively.

Good to know

Low seasonAugust
Cheapest flight$250
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 26% lower on average.
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 9768 reviews
7.7Boarding
7.1Entertainment
6.6Food
7.3Comfort
8.1Crew
Airline reviews

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

10.0 ExcellentJanice, Jun 2026
ORD - ILM
Read more United Airlines reviews

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Boarded early, left early, arrived 40 mins early! A win win for me!

New plane was lovely. Crew customer service is always lax but expected. Kraft on time and arrived safely.

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports