Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Charlottesville to Caribbean Islands from $155

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Charlottesville to Caribbean Islands departing on 2/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Charlottesville to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
4:33 pm - 10:09 amCHO-SJU
16h 36m2 stops
American Airlines Logo
5:56 pm - 10:27 amSJU-CHO
17h 31m1 stop
$295American Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 10
Delta Logo
6:00 am - 5:28 pmCHO-SJU
10h 28m1 stop
Delta Logo
7:00 am - 5:23 pmSJU-CHO
11h 23m1 stop
$302Delta
Find Deal
Mon, Dec 8 - Wed, Dec 10
American Airlines Logo
7:09 pm - 2:55 pmCHO-PUJ
18h 46m2 stops
American Airlines Logo
5:33 pm - 11:58 amPUJ-CHO
19h 25m2 stops
$306American Airlines
Find Deal
Sun, Feb 1 - Fri, Feb 6
American Airlines Logo
7:09 pm - 12:55 pmCHO-PUJ
16h 46m1 stop
American Airlines Logo
3:04 pm - 9:54 amPUJ-CHO
19h 50m1 stop
$308American Airlines
Find Deal
Sun, Feb 1 - Fri, Feb 6
United Airlines Logo
2:40 pm - 1:33 pmCHO-NAS
22h 53m2 stops
United Airlines Logo
1:05 pm - 11:42 pmNAS-CHO
10h 37m1 stop
$334United Airlines
Find Deal
Tue, Oct 28 - Sat, Nov 8
Delta Logo
6:00 am - 5:28 pmCHO-SJU
10h 28m1 stop
Delta Logo
7:00 am - 5:23 pmSJU-CHO
11h 23m1 stop
$335Delta
Find Deal
Mon, Dec 8 - Wed, Dec 10
Delta Logo
6:00 am - 1:30 pmCHO-NAS
7h 30m1 stop
Delta Logo
3:40 pm - 10:34 pmNAS-CHO
6h 54m1 stop
$345Delta
Find Deal
Tue, Mar 10 - Wed, Mar 11
United Airlines Logo
10:55 am - 12:36 amCHO-SJU
12h 41m2 stops
United Airlines Logo
5:50 pm - 11:42 pmSJU-CHO
6h 52m1 stop
$415United Airlines
Find Deal
Tue, Nov 18 - Thu, Nov 20
Multiple Airlines Logo
8:15 pm - 3:43 pmCHO-STT
19h 28m2 stops
Multiple Airlines Logo
9:49 am - 1:26 pmSTT-CHO
27h 37m2 stops
$878Multiple Airlines
Find Deal
Fri, Apr 3 - Fri, Apr 10
Multiple Airlines Logo
5:40 pm - 5:00 pmCHO-STT
23h 20m1 stop
Multiple Airlines Logo
9:10 am - 1:26 pmSTT-CHO
28h 16m2 stops
$991Multiple Airlines
Find Deal
Fri, Apr 3 - Fri, Apr 10

Delta flights from Charlottesville to Caribbean Islands

Our best Delta deals on Charlottesville to Caribbean Islands flight tickets
Delta
Dec 8
CHO6:00 amCharlottesville Albemarle
10h 28m
1 stop
SJU5:28 pmSan Juan Luis Munoz Marin Intl
Dec 10
SJU7:00 amSan Juan Luis Munoz Marin Intl
11h 23m
1 stop
CHO5:23 pmCharlottesville Albemarle
$302
Find similar
Delta
Dec 8
CHO6:00 amCharlottesville Albemarle
10h 28m
1 stop
SJU5:28 pmSan Juan Luis Munoz Marin Intl
Dec 10
SJU7:00 amSan Juan Luis Munoz Marin Intl
11h 23m
1 stop
CHO5:23 pmCharlottesville Albemarle
$335
Find similar
Delta
Mar 10
CHO6:00 amCharlottesville Albemarle
7h 30m
1 stop
NAS1:30 pmNassau Intl
Mar 11
NAS3:40 pmNassau Intl
6h 54m
1 stop
CHO10:34 pmCharlottesville Albemarle
$345
Find similar

American Airlines flights from Charlottesville to Caribbean Islands

Our best American Airlines deals on Charlottesville to Caribbean Islands flight tickets
American Airlines
Dec 8
CHO4:33 pmCharlottesville Albemarle
16h 36m
2 stops
SJU10:09 amSan Juan Luis Munoz Marin Intl
Dec 10
SJU5:56 pmSan Juan Luis Munoz Marin Intl
17h 31m
1 stop
CHO10:27 amCharlottesville Albemarle
$295
Find similar
American Airlines
Feb 1
CHO7:09 pmCharlottesville Albemarle
18h 46m
2 stops
PUJ2:55 pmPunta Cana
Feb 6
PUJ5:33 pmPunta Cana
19h 25m
2 stops
CHO11:58 amCharlottesville Albemarle
$306
Find similar
American Airlines
Feb 1
CHO7:09 pmCharlottesville Albemarle
16h 46m
1 stop
PUJ12:55 pmPunta Cana
Feb 6
PUJ3:04 pmPunta Cana
19h 50m
1 stop
CHO9:54 amCharlottesville Albemarle
$308
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Charlottesville to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 9, 2025.
Use the filters below to find and compare flights from Charlottesville to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

4:33 pm-10:09 am

2 stops16h 36m

San Juan Luis Munoz Marin Intl

Wed 12/10

5:56 pm-10:27 am

1 stop17h 31m

$295

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

6:00 am-5:28 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:00 am-5:23 pm

1 stop11h 23m

$302

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

7:09 pm-2:55 pm

2 stops18h 46m

Punta Cana

Fri 2/6

5:33 pm-11:58 am

2 stops19h 25m

$306

CharlottesvillePunta Cana

CHO - PUJ

CHOPUJ

Charlottesville Albemarle

Sun 2/1

7:09 pm-12:55 pm

1 stop16h 46m

Punta Cana

Fri 2/6

3:04 pm-9:54 am

1 stop19h 50m

$308

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Tue 10/28

2:40 pm-1:33 pm

2 stops22h 53m

Nassau Intl

Sat 11/8

1:05 pm-11:42 pm

1 stop10h 37m

$334

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Mon 12/8

6:00 am-5:28 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:00 am-5:23 pm

1 stop11h 23m

$335

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Tue 3/10

6:00 am-1:30 pm

1 stop7h 30m

Nassau Intl

Wed 3/11

3:40 pm-10:34 pm

1 stop6h 54m

$345

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Tue 11/18

10:55 am-12:36 am

2 stops12h 41m

San Juan Luis Munoz Marin Intl

Thu 11/20

5:50 pm-11:42 pm

1 stop6h 52m

$415

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Fri 4/3

8:15 pm-3:43 pm

2 stops19h 28m

Saint Thomas Island Cyril E King

Fri 4/10

9:49 am-1:26 pm

2 stops27h 37m

$878

CharlottesvilleSaint Thomas Island

CHO - STT

CHOSTT

Charlottesville Albemarle

Fri 4/3

5:40 pm-5:00 pm

1 stop23h 20m

Saint Thomas Island Cyril E King

Fri 4/10

9:10 am-1:26 pm

2 stops28h 16m

$991

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Charlottesville to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of December is, on average, the cheapest month to fly to Caribbean Islands from Charlottesville, with most prices found around $410. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Charlottesville averaging around $421.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Charlottesville to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $443. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $701. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the morning. momondo users have found flights departing from Charlottesville to Caribbean Islands in the morning for as low as $568. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $714. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Charlottesville to Caribbean Islands flights?

You could potentially save up to 62% on your flight if you consider stops on a Charlottesville to Caribbean Islands flight.

Cheap Charlottesville to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charlottesville to Caribbean Islands

Direct flights

None
There are no direct flights from Charlottesville to Caribbean Islands. There are no popular flight routes from Charlottesville to Caribbean Islands.
Search flight deals

  • When did momondo last update prices for flights from Charlottesville Albemarle Airport to Caribbean Islands?

    Prices for flights from Charlottesville Albemarle Airport to Caribbean Islands were last updated today.

  • How many operators does momondo search for flights from Charlottesville Albemarle Airport to Caribbean Islands?

  • How old do you have to be to fly from Charlottesville Albemarle Airport to Caribbean Islands?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Charlottesville Albemarle Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Charlottesville to Caribbean Islands?

Best airlines flying from Charlottesville to Caribbean Islands

Compare and see reviews for airlines that fly from Charlottesville to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $261Free CancellationRating
7.4
8,968 reviews
Search United Airlines flights
DeltaPriceFrom $311Free CancellationRating
7.9
7,969 reviews
Search Delta flights
American AirlinesPriceFrom $425Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Charlottesville to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Charlottesville to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Charlottesville to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Charlottesville with this policy.

How can momondo help me find flights from Charlottesville to Caribbean Islands?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from Charlottesville.

I’m not ready to book a flight from Charlottesville to Caribbean Islands right now. Can momondo alert me if prices change?

Price alerts on flights to Caribbean Islands from Charlottesville are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/8
Sat 11/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Londonfrom $315
Flights to Bangkokfrom $508
Flights to Tokyofrom $378
Flights to Los Angelesfrom $38
Flights to Parisfrom $329
Flights to Copenhagenfrom $342
Flights to Istanbulfrom $376
Flights to Manilafrom $523
Flights to Romefrom $323
Flights to Miamifrom $60
Flights to Chicagofrom $49