$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 2/24. 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$323
Montego Bay
Montego Bay1 stop$337
Nassau
Nassau1 stop$322
Simpson Bay
Simpson Bay1 stop$456
George Town
George Town2 stops$334
Puerto Plata
Puerto Plata1 stop$2,328
Punta Cana
Punta Cana2 stops$323
Montego Bay
Montego Bay1 stop$337
Nassau
Nassau1 stop$322
Simpson Bay
Simpson Bay1 stop$456
George Town
George Town2 stops$334
Puerto Plata
Puerto Plata1 stop$2,328

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, Feb 25 - Wed, Mar 4
Delta Logo
2:29 pm - 11:58 pm
CHO
-
SJU
8h 29m
1 stop
Delta Logo
6:15 am - 1:46 pm
SJU
-
CHO
8h 31m
1 stop
$232Delta
Wed, Feb 25 - Fri, Mar 6
Delta Logo
2:29 pm - 11:58 pm
CHO
-
SJU
8h 29m
1 stop
Delta Logo
6:15 am - 1:46 pm
SJU
-
CHO
8h 31m
1 stop
$274Delta
Tue, Mar 3 - Thu, Mar 5
United Airlines Logo
6:20 am - 1:17 pm
CHO
-
SJU
5h 57m
1 stop
United Airlines Logo
4:52 pm - 12:09 am
SJU
-
CHO
8h 17m
1 stop
$322United Airlines
Wed, Feb 25 - Wed, Mar 4
Delta Logo
7:00 am - 3:13 pm
CHO
-
NAS
8h 13m
1 stop
Delta Logo
4:23 pm - 10:47 pm
NAS
-
CHO
6h 24m
1 stop
$322Delta
Sat, Feb 21 - Tue, Mar 3
American Airlines Logo
7:57 pm - 12:01 pm
CHO
-
PUJ
15h 04m
2 stops
American Airlines Logo
12:50 pm - 9:47 am
PUJ
-
CHO
21h 57m
2 stops
$323American Airlines
Mon, Feb 9 - Fri, Feb 13
American Airlines Logo
5:20 pm - 12:05 pm
CHO
-
GCM
18h 45m
2 stops
American Airlines Logo
12:55 pm - 8:27 am
GCM
-
CHO
19h 32m
2 stops
$334American Airlines
Mon, Feb 9 - Fri, Feb 13
American Airlines Logo
7:09 pm - 11:26 am
CHO
-
GCM
16h 17m
1 stop
American Airlines Logo
12:53 pm - 8:27 am
GCM
-
CHO
19h 34m
1 stop
$335American Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
7:13 pm - 9:13 am
CHO
-
MBJ
15h 00m
1 stop
American Airlines Logo
4:44 pm - 12:57 pm
MBJ
-
CHO
19h 13m
2 stops
$337American Airlines
Mon, Apr 13 - Thu, Apr 16
United Airlines Logo
6:20 am - 8:34 pm
CHO
-
SJU
14h 14m
2 stops
United Airlines Logo
1:00 am - 9:58 am
SJU
-
CHO
8h 58m
2 stops
$340United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
6:20 am - 3:10 pm
CHO
-
MBJ
9h 50m
1 stop
United Airlines Logo
4:12 pm - 9:58 am
MBJ
-
CHO
16h 46m
1 stop
$340United Airlines
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 $438, 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 19% drop in price.
Most popular time to fly and prices are also 9% 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.

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 9215 reviews
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
7.3Comfort
Airline reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

2.0 MediocreJames, Jan 2026
ORD - MSP
Read more United Airlines reviews

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports