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Cheap flights from Charlottesville to Caribbean Islands from $107

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 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Charlottesville to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
3:02 pm - 11:45 pmCHO-SJU
7h 43m1 stop
Delta Logo
7:30 am - 4:45 pmSJU-CHO
10h 15m1 stop
$231Delta
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Sun, Jan 25 - Thu, Jan 29
American Airlines Logo
4:45 pm - 10:48 amCHO-SJU
17h 03m2 stops
American Airlines Logo
6:00 am - 4:07 pmSJU-CHO
11h 07m2 stops
$291American Airlines
Find Deal
Sun, Jan 25 - Thu, Jan 29
Delta Logo
6:00 am - 11:50 amCHO-NAS
5h 50m1 stop
Delta Logo
4:28 pm - 10:39 pmNAS-CHO
6h 11m1 stop
$295Delta
Find Deal
Sat, Jan 10 - Wed, Jan 14
Delta Logo
6:00 am - 2:55 pmCHO-SXM
7h 55m1 stop
Delta Logo
1:55 pm - 10:51 pmSXM-CHO
9h 56m1 stop
$297Delta
Find Deal
Mon, Jan 26 - Thu, Jan 29
American Airlines Logo
7:09 pm - 4:28 pmCHO-SXM
20h 19m2 stops
American Airlines Logo
5:33 pm - 9:59 amSXM-CHO
17h 26m2 stops
$298American Airlines
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Fri, Jan 30 - Mon, Feb 2
Delta Logo
6:00 am - 11:50 amCHO-NAS
5h 50m1 stop
Delta Logo
2:40 pm - 1:54 pmNAS-CHO
23h 14m2 stops
$299Delta
Find Deal
Sat, Jan 10 - Wed, Jan 14
American Airlines Logo
5:20 pm - 1:42 pmCHO-SXM
19h 22m1 stop
American Airlines Logo
3:09 pm - 11:19 pmSXM-CHO
9h 10m1 stop
$299American Airlines
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Sat, Jan 31 - Wed, Feb 4
United Airlines Logo
8:29 pm - 1:37 pmCHO-MBJ
18h 08m2 stops
United Airlines Logo
4:12 pm - 10:52 pmMBJ-CHO
5h 40m1 stop
$315United Airlines
Find Deal
Mon, Mar 23 - Mon, Mar 30
United Airlines Logo
2:41 pm - 6:11 amCHO-SJU
14h 30m2 stops
United Airlines Logo
2:05 am - 1:42 pmSJU-CHO
12h 37m2 stops
$328United Airlines
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Sun, Jan 25 - Fri, Jan 30
WestJet Logo
11:58 am - 2:58 pmCHO-BGI
50h 00m2 stops
WestJet Logo
3:50 pm - 6:50 pmBGI-CHO
28h 00m2 stops
$3,499WestJet
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Mon, Jan 19 - Fri, Jan 23

United Airlines flights from Charlottesville to Caribbean Islands

Our best United Airlines deals on Charlottesville to Caribbean Islands flight tickets
United Airlines
Mar 23
CHO8:29 pmCharlottesville Albemarle
18h 08m
2 stops
MBJ1:37 pmMontego Bay Sangster Intl
Mar 30
MBJ4:12 pmMontego Bay Sangster Intl
5h 40m
1 stop
CHO10:52 pmCharlottesville Albemarle
$315
Find similar
United Airlines
Jan 25
CHO2:41 pmCharlottesville Albemarle
14h 30m
2 stops
SJU6:11 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU2:05 amSan Juan Luis Munoz Marin Intl
12h 37m
2 stops
CHO1:42 pmCharlottesville Albemarle
$328
Find similar
United Airlines
Mar 17
CHO6:50 amCharlottesville Albemarle
6h 56m
1 stop
MBJ12:46 pmMontego Bay Sangster Intl
Mar 24
MBJ2:20 pmMontego Bay Sangster Intl
22h 39m
2 stops
CHO1:59 pmCharlottesville Albemarle
$332
Find similar

American Airlines flights from Charlottesville to Caribbean Islands

Our best American Airlines deals on Charlottesville to Caribbean Islands flight tickets
American Airlines
Jan 25
CHO4:45 pmCharlottesville Albemarle
17h 03m
2 stops
SJU10:48 amSan Juan Luis Munoz Marin Intl
Jan 29
SJU6:00 amSan Juan Luis Munoz Marin Intl
11h 07m
2 stops
CHO4:07 pmCharlottesville Albemarle
$291
Find similar
American Airlines
Jan 30
CHO7:09 pmCharlottesville Albemarle
20h 19m
2 stops
SXM4:28 pmSimpson Bay Princess Juliana
Feb 2
SXM5:33 pmSimpson Bay Princess Juliana
17h 26m
2 stops
CHO9:59 amCharlottesville Albemarle
$298
Find similar
American Airlines
Jan 31
CHO5:20 pmCharlottesville Albemarle
19h 22m
1 stop
SXM1:42 pmSimpson Bay Princess Juliana
Feb 4
SXM3:09 pmSimpson Bay Princess Juliana
9h 10m
1 stop
CHO11:19 pmCharlottesville Albemarle
$299
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 December 3, 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

Sun 1/25

3:02 pm-11:45 pm

1 stop7h 43m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-4:45 pm

1 stop10h 15m

$231

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sun 1/25

4:45 pm-10:48 am

2 stops17h 03m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:00 am-4:07 pm

2 stops11h 07m

$291

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Sat 1/10

6:00 am-11:50 am

1 stop5h 50m

Nassau Intl

Wed 1/14

4:28 pm-10:39 pm

1 stop6h 11m

$295

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 1/26

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Thu 1/29

1:55 pm-10:51 pm

1 stop9h 56m

$297

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 1/30

7:09 pm-4:28 pm

2 stops20h 19m

Simpson Bay Princess Juliana

Mon 2/2

5:33 pm-9:59 am

2 stops17h 26m

$298

CharlottesvilleNassau

CHO - NAS

CHONAS

Charlottesville Albemarle

Sat 1/10

6:00 am-11:50 am

1 stop5h 50m

Nassau Intl

Wed 1/14

2:40 pm-1:54 pm

2 stops23h 14m

$299

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 1/31

5:20 pm-1:42 pm

1 stop19h 22m

Simpson Bay Princess Juliana

Wed 2/4

3:09 pm-11:19 pm

1 stop9h 10m

$299

CharlottesvilleMontego Bay

CHO - MBJ

CHOMBJ

Charlottesville Albemarle

Mon 3/23

8:29 pm-1:37 pm

2 stops18h 08m

Montego Bay Sangster Intl

Mon 3/30

4:12 pm-10:52 pm

1 stop5h 40m

$315

CharlottesvilleSan Juan

CHO - SJU

CHOSJU

Charlottesville Albemarle

Sun 1/25

2:41 pm-6:11 am

2 stops14h 30m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-1:42 pm

2 stops12h 37m

$328

CharlottesvilleBridgetown

CHO - BGI

CHOBGI

Charlottesville Albemarle

Mon 1/19

11:58 am-2:58 pm

2 stops50h 00m

Bridgetown Grantley Adams Intl

Fri 1/23

3:50 pm-6:50 pm

2 stops28h 00m

$3,499

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 60% 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

Fastest flight time

5h 09m

Direct flights

None
The fastest flight from Charlottesville to Caribbean Islands takes 5h 09m
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
9,063 reviews
Search United Airlines flights
DeltaPriceFrom $311Free CancellationRating
7.9
8,011 reviews
Search Delta flights
American AirlinesPriceFrom $367Free CancellationRating
7.2
11,045 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.

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