$224 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 7/9. 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

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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Flights Deals

Best Caribbean Islands Flight Deals from Charlottesville

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$431
Santo Domingo
Santo Domingo2 stops$686
Montego Bay
Montego Bay1 stop$438
Nassau
Nassau1 stop$511
Simpson Bay
Simpson Bay2 stops$597
George Town
George Town2 stops$487
Puerto Plata
Puerto Plata2 stops$689
Punta Cana
Punta Cana1 stop$431
Santo Domingo
Santo Domingo2 stops$686
Montego Bay
Montego Bay1 stop$438
Nassau
Nassau1 stop$511
Simpson Bay
Simpson Bay2 stops$597
George Town
George Town2 stops$487
Puerto Plata
Puerto Plata2 stops$689

Cheap Flights from Charlottesville to Caribbean Islands

 
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, Nov 12 - Tue, Nov 18
Delta Logo
3:05 pm - 11:17 pmCHO-SJU
7h 12m1 stop
Delta Logo
7:30 am - 4:47 pmSJU-CHO
10h 17m1 stop
$275Delta
Find Deal
Fri, Oct 31 - Tue, Nov 4
Delta Logo
6:00 am - 1:23 pmCHO-SJU
7h 23m1 stop
Delta Logo
3:28 pm - 10:39 pmSJU-CHO
8h 11m1 stop
$303Delta
Find Deal
Tue, Nov 4 - Mon, Nov 10
United Airlines Logo
6:30 am - 1:17 pmCHO-SJU
5h 47m1 stop
United Airlines Logo
5:50 pm - 11:00 pmSJU-CHO
6h 10m1 stop
$341United Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 10
United Airlines Logo
3:00 pm - 10:22 pmCHO-SJU
6h 22m1 stop
United Airlines Logo
8:30 am - 1:26 pmSJU-CHO
5h 56m1 stop
$381United Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 10
United Airlines Logo
3:00 pm - 10:22 pmCHO-SJU
6h 22m1 stop
United Airlines Logo
8:30 am - 1:26 pmSJU-CHO
5h 56m1 stop
$421United Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
United Airlines Logo
3:00 pm - 9:22 pmCHO-SJU
6h 22m1 stop
United Airlines Logo
2:05 am - 4:58 pmSJU-CHO
15h 53m2 stops
$428United Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 10
American Airlines Logo
2:02 pm - 12:05 pmCHO-SJU
21h 03m2 stops
American Airlines Logo
2:30 pm - 11:56 pmSJU-CHO
10h 26m1 stop
$438American Airlines
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Fri, Aug 15 - Fri, Aug 22
American Airlines Logo
9:32 am - 12:20 pmCHO-MBJ
27h 48m1 stop
American Airlines Logo
11:45 am - 8:33 amMBJ-CHO
19h 48m1 stop
$438American Airlines
Find Deal
Tue, Aug 5 - Sat, Aug 9
 Logo
6:10 am - 6:00 pmCHO-STT
11h 50m2 stops
 Logo
4:00 pm - 1:49 pmSTT-CHO
21h 49m2 stops
$1,325
Find Deal
Fri, Sep 5 - Tue, Sep 9
WestJet Logo
5:48 am - 8:57 amCHO-PUJ
27h 09m2 stops
WestJet Logo
12:25 pm - 11:11 amPUJ-CHO
22h 46m2 stops
$1,369WestJet
Find Deal
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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 $680, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charlottesville to Caribbean Islands, 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 Islands is November, when tickets cost $261 (return) on average. On the other hand, the most expensive months are July and September, when the average cost of round-trip tickets is $692 and $620 respectively.


Good to know

Low seasonSeptember
High seasonApril
Cheapest flight$224
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 17% increase in price.
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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $568 on average. Morning departures are around 20% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $714.

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 8861 reviews
7.3Comfort
6.6Food
8.1Crew
7.7Boarding
7.0Entertainment
Airline reviews

We love united ! We would like to acknowledge Aimee in the lounge near gate 130

10.0 ExcellentGal, Jul 2025EWR - NCE
Read more United Airlines reviews

We love united ! We would like to acknowledge Aimee in the lounge near gate 130

Boarded plane and then delayed 1.5 hours while on the plane

Although the flight was delayed the crew and the flight itself were very good. Couldn't fault anything and after the disappointment of being abandoned in the US by BA it was a welcome relief to travel with United

Survey sent before we actually left. Delay after delay. Now a crew problem.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

online check in was not available so i had to get to airport extra early. The flight was delayed and my luggage was lost. I had an argument with the person behind me who wanted to keep her bag on the floor and not allow my seat to recline on a 9hr plus flight. So overall, lots and lots of areas for improvement.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

My flight was delayed a very short period of time but they did not hold my connecting flight to San Diego, also through United. So they closed the doors before we got off our plane. They would only have to help the door open for another five to ten minutes. So I missed a court deadline for a manditory mediation settlement conference for my client. I had to get an associate to be there in person and be on the phone with him relaying what he needs to do the entire time. The court was very upset with me and so was my client. United cannot be trusted.

Very rough getting into denver. my kid threw up it was so rough.

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

The flight delay in Dallas created a domino effect that impacted all of the connecting flights. It also increased the number of connections. I missed my flight from Casablanca to Marrakech because of the tight turnaround when landing in Casablanca. . CMN airport was understaffed. Only one person could help while other employees were just watching him. It was an extremely frustrating situation. People were crying and slamming their palms on the counter when speaking to the customer service provider, Allabough (man’s name?). Allabough couldn’t change my flight in the system. simultaneously, I was on the call with America. Airlines customer service rep named Solomon that said he couldn’t change it either. So, I took a ONYA voyages train to from Casablanca to Marrakech to get there on Friday June 26. This was unpredictable trip.

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

Everything you need to know for your flight to Caribbean Islands

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