$140 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 1/15. 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$303
Santo Domingo
Santo Domingo2 stops$319
Montego Bay
Montego Bay1 stop$332
Nassau
Nassau1 stop$326
Simpson Bay
Simpson Bay2 stops$306
George Town
George Town1 stop$419
Puerto Plata
Puerto Plata2 stops$614
Punta Cana
Punta Cana1 stop$303
Santo Domingo
Santo Domingo2 stops$319
Montego Bay
Montego Bay1 stop$332
Nassau
Nassau1 stop$326
Simpson Bay
Simpson Bay2 stops$306
George Town
George Town1 stop$419
Puerto Plata
Puerto Plata2 stops$614

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 - Wed, Feb 25
American Airlines Logo
7:57 pm - 1:53 pm
CHO
-
SJU
16h 56m1 stop
American Airlines Logo
8:40 am - 6:52 pm
SJU
-
CHO
11h 12m1 stop
$232American Airlines
Sun, Feb 22 - Tue, Feb 24
United Airlines Logo
6:20 am - 9:26 pm
CHO
-
SJU
14h 06m2 stops
United Airlines Logo
2:05 am - 1:59 pm
SJU
-
CHO
12h 54m2 stops
$264United Airlines
Mon, Feb 23 - Fri, Feb 27
American Airlines Logo
7:57 pm - 12:58 pm
CHO
-
PUJ
16h 01m1 stop
American Airlines Logo
5:01 pm - 8:27 am
PUJ
-
CHO
16h 26m1 stop
$303American Airlines
Thu, Feb 26 - Thu, Mar 5
American Airlines Logo
7:57 pm - 4:28 pm
CHO
-
SXM
19h 31m2 stops
American Airlines Logo
1:29 pm - 8:27 am
SXM
-
CHO
19h 58m2 stops
$306American Airlines
Sun, Feb 1 - Fri, Feb 6
American Airlines Logo
7:09 pm - 11:54 am
CHO
-
PUJ
15h 45m2 stops
American Airlines Logo
5:26 pm - 9:59 am
PUJ
-
CHO
17h 33m2 stops
$307American Airlines
Sun, Feb 1 - Fri, Feb 6
American Airlines Logo
7:09 pm - 12:55 pm
CHO
-
PUJ
16h 46m1 stop
American Airlines Logo
5:33 pm - 11:58 am
PUJ
-
CHO
19h 25m1 stop
$309American Airlines
Mon, Jan 26 - Wed, Jan 28
United Airlines Logo
2:41 pm - 10:22 pm
CHO
-
SJU
6h 41m1 stop
United Airlines Logo
2:05 am - 1:42 pm
SJU
-
CHO
12h 37m2 stops
$322United Airlines
Tue, Feb 17 - Mon, Feb 23
Delta Logo
11:53 am - 5:02 pm
CHO
-
NAS
5h 09m1 stop
Delta Logo
2:59 pm - 10:49 pm
NAS
-
CHO
7h 50m1 stop
$326Delta
Sun, Feb 1 - Sun, Feb 8
Delta Logo
12:03 pm - 5:02 pm
CHO
-
NAS
4h 59m1 stop
Delta Logo
6:27 pm - 1:54 pm
NAS
-
CHO
19h 27m2 stops
$330Delta
Fri, Feb 6 - Fri, Feb 13
Delta Logo
12:03 pm - 5:02 pm
CHO
-
NAS
4h 59m1 stop
Delta Logo
4:23 pm - 10:47 pm
NAS
-
CHO
6h 24m1 stop
$364Delta
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 fly non-stop between Charlottesville and Caribbean?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Charlottesville to Caribbean.

There are 2 airlines that fly nonstop from Charlottesville to Caribbean. They are American Airlines and United Airlines. The cheapest airline for this route is American Airlines, with the best round-trip deal found costing $367 and arriving in Nassau (NAS). On average, United Airlines offers the best prices for nonstop flights between Charlottesville and Caribbean.

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 ($322).

Good to know

Low seasonAugust
Cheapest flight$118
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 George Town

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 9138 reviews
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

6.0 GoodTobin, Jan 2026
LAX - CUN
Read more United Airlines reviews

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Aircraft was noisy, old and never dimmed the lights on a night flight even on business class! I flew 17 times on United and probably another 40 on other airlines United USA /Europe flights were the worst to include luggage delayed once going to europe and once coming back

Check how old the airframe is, some older ones have inoperable seat back entertainment or power.

The economy seats are very cramped and the food was bizarre. However, I did like the greek yogurt option for breakfast.

While I didn’t watch much tv I would have liked a few more options of TV series from Apple TV or hbo max ..

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Experience was good. We were delayed in leaving by 15 mins because the flight was waiting on a family that was late in getting to the gate. Food and drink options were as expected. I highly recommend checking in ahead of time using the airline’s app so that it’s quicker to get your luggage tags as soon as you arrive at the terminal. No more waiting in long lines!

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports