$187 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 5/8. 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

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

Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$420
Santo Domingo
Santo Domingo2 stops$391
Montego Bay
Montego Bay2 stops$357
Nassau
Nassau2 stops$341
Simpson Bay
Simpson Bay2 stops$406
George Town
George Town2 stops$334
Punta Cana
Punta Cana1 stop$420
Santo Domingo
Santo Domingo2 stops$391
Montego Bay
Montego Bay2 stops$357
Nassau
Nassau2 stops$341
Simpson Bay
Simpson Bay2 stops$406
George Town
George Town2 stops$334

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, May 10 - Sat, May 16
American Airlines Logo
8:10 pm - 1:10 pm
CHO
-
GCM
18h 00m
2 stops
American Airlines Logo
2:10 pm - 8:39 am
GCM
-
CHO
17h 29m
2 stops
$334American Airlines
Thu, Sep 24 - Mon, Sep 28
United Airlines Logo
7:45 pm - 1:47 pm
CHO
-
NAS
18h 02m
2 stops
United Airlines Logo
2:53 pm - 9:26 am
NAS
-
CHO
18h 33m
2 stops
$341United Airlines
Sat, May 30 - Sat, Jun 6
American Airlines Logo
8:00 pm - 11:45 am
CHO
-
MBJ
16h 45m
2 stops
American Airlines Logo
2:08 pm - 8:33 am
MBJ
-
CHO
17h 25m
2 stops
$357American Airlines
Thu, May 28 - Thu, Jun 4
American Airlines Logo
8:00 pm - 12:45 pm
CHO
-
SDQ
16h 45m
2 stops
American Airlines Logo
2:15 pm - 8:33 am
SDQ
-
CHO
18h 18m
2 stops
$391American Airlines
Fri, Oct 2 - Sun, Jan 31
American Airlines Logo
8:25 pm - 12:25 pm
CHO
-
SDQ
16h 00m
2 stops
American Airlines Logo
6:29 pm - 11:58 am
SDQ
-
CHO
18h 29m
2 stops
$396American Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
8:00 pm - 10:03 am
CHO
-
NAS
14h 03m
1 stop
American Airlines Logo
2:18 pm - 11:54 pm
NAS
-
CHO
9h 36m
1 stop
$396American Airlines
Sun, Jul 19 - Wed, Jul 22
United Airlines Logo
6:25 am - 12:33 pm
CHO
-
SXM
6h 08m
1 stop
United Airlines Logo
3:50 pm - 9:56 am
SXM
-
CHO
18h 06m
1 stop
$438United Airlines
Fri, Jul 3 - Tue, Jul 7
Delta Logo
6:00 am - 2:19 pm
CHO
-
STT
8h 19m
1 stop
Delta Logo
1:21 pm - 11:14 pm
STT
-
CHO
9h 53m
1 stop
$684Delta
Wed, Jun 17 - Sun, Jun 21
Delta Logo
6:00 am - 1:16 pm
CHO
-
SDQ
7h 16m
1 stop
Delta Logo
2:41 pm - 11:13 pm
SDQ
-
CHO
8h 32m
1 stop
$914Delta
Wed, Jun 17 - Sun, Jun 21
Delta Logo
6:00 am - 1:16 pm
CHO
-
SDQ
7h 16m
1 stop
Delta Logo
2:41 pm - 11:13 pm
SDQ
-
CHO
8h 32m
1 stop
$930Delta
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 April, when tickets cost $254 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $492 and $461 respectively.

Good to know

Low seasonAugust
Cheapest flight$158
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Charlottesville to Nassau

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 9677 reviews
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
Airline reviews

Some crew were unfriendly or in some cases just straight up rude.

6.0 GoodAnonymous, Apr 2026
SFO - YVR
Read more United Airlines reviews

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports