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Cheap flights from Charlottesville to Simpson Bay from $350

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Charlottesville to Simpson Bay departing on 4/16. 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

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Find the cheapest flights from Charlottesville to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:03 pm - 1:16 pm
CHO
-
SXM
17h 13m
2 stops
American Airlines Logo
12:41 pm - 12:57 pm
SXM
-
CHO
24h 16m
2 stops
$350American Airlines
Thu, Apr 16 - Tue, Apr 21
American Airlines Logo
8:03 pm - 1:16 pm
CHO
-
SXM
17h 13m
2 stops
American Airlines Logo
2:24 pm - 11:54 pm
SXM
-
CHO
9h 30m
1 stop
$484American Airlines
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
7:57 pm - 3:00 pm
CHO
-
SXM
19h 03m
2 stops
American Airlines Logo
4:28 pm - 1:12 pm
SXM
-
CHO
20h 44m
2 stops
$527American Airlines
Wed, Apr 1 - Sun, Apr 5
American Airlines Logo
8:02 pm - 12:45 pm
CHO
-
SXM
16h 43m
2 stops
American Airlines Logo
1:45 pm - 8:34 am
SXM
-
CHO
18h 49m
2 stops
$534American Airlines
Sun, Jul 5 - Sun, Jul 12
American Airlines Logo
8:02 pm - 1:22 pm
CHO
-
SXM
17h 20m
2 stops
American Airlines Logo
1:45 pm - 8:34 am
SXM
-
CHO
18h 49m
2 stops
$544American Airlines
Sun, Jul 5 - Sun, Jul 12
American Airlines Logo
6:06 pm - 2:19 pm
CHO
-
SXM
19h 13m
2 stops
American Airlines Logo
1:29 pm - 8:27 am
SXM
-
CHO
19h 58m
2 stops
$567American Airlines
Thu, Feb 26 - Thu, Mar 5
American Airlines Logo
4:20 pm - 2:19 pm
CHO
-
SXM
20h 59m
2 stops
American Airlines Logo
3:21 pm - 8:27 am
SXM
-
CHO
18h 06m
1 stop
$577American Airlines
Thu, Feb 26 - Thu, Mar 5
American Airlines Logo
8:02 pm - 3:31 pm
CHO
-
SXM
19h 29m
2 stops
American Airlines Logo
2:45 pm - 8:34 am
SXM
-
CHO
17h 49m
1 stop
$579American Airlines
Sun, Jul 5 - Sun, Jul 12
American Airlines Logo
8:02 pm - 12:45 pm
CHO
-
SXM
16h 43m
2 stops
American Airlines Logo
2:45 pm - 8:34 am
SXM
-
CHO
17h 49m
1 stop
$589American Airlines
Sun, Jul 5 - Sun, Jul 12
American Airlines Logo
4:20 pm - 12:29 pm
CHO
-
SXM
19h 09m
2 stops
American Airlines Logo
1:29 pm - 8:27 am
SXM
-
CHO
19h 58m
2 stops
$607American Airlines
Thu, Feb 26 - Thu, Mar 5

American Airlines flights from Charlottesville to Simpson Bay

Our best American Airlines deals on Charlottesville to Simpson Bay flight tickets
American Airlines
Apr 16
CHO8:03 pmCharlottesville Albemarle
17h 13m
2 stops
SXM1:16 pmSimpson Bay Princess Juliana
Apr 21
SXM12:41 pmSimpson Bay Princess Juliana
24h 16m
2 stops
CHO12:57 pmCharlottesville Albemarle
$350
American Airlines
Apr 16
CHO8:03 pmCharlottesville Albemarle
17h 13m
2 stops
SXM1:16 pmSimpson Bay Princess Juliana
Apr 20
SXM2:24 pmSimpson Bay Princess Juliana
9h 30m
1 stop
CHO11:54 pmCharlottesville Albemarle
$484
American Airlines
Apr 1
CHO7:57 pmCharlottesville Albemarle
19h 03m
2 stops
SXM3:00 pmSimpson Bay Princess Juliana
Apr 5
SXM4:28 pmSimpson Bay Princess Juliana
20h 44m
2 stops
CHO1:12 pmCharlottesville Albemarle
$527

momondo Fare Finder

 
Customize your flight search to find flights from Charlottesville to Simpson Bay 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 February 11, 2026.
Use the filters below to find and compare flights from Charlottesville to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 4/16

8:03 pm-1:16 pm

2 stops17h 13m

Simpson Bay Princess Juliana

Tue 4/21

12:41 pm-12:57 pm

2 stops24h 16m

$350

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 4/16

8:03 pm-1:16 pm

2 stops17h 13m

Simpson Bay Princess Juliana

Mon 4/20

2:24 pm-11:54 pm

1 stop9h 30m

$484

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Wed 4/1

7:57 pm-3:00 pm

2 stops19h 03m

Simpson Bay Princess Juliana

Sun 4/5

4:28 pm-1:12 pm

2 stops20h 44m

$527

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 7/5

8:02 pm-12:45 pm

2 stops16h 43m

Simpson Bay Princess Juliana

Sun 7/12

1:45 pm-8:34 am

2 stops18h 49m

$534

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 7/5

8:02 pm-1:22 pm

2 stops17h 20m

Simpson Bay Princess Juliana

Sun 7/12

1:45 pm-8:34 am

2 stops18h 49m

$544

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 2/26

6:06 pm-2:19 pm

2 stops19h 13m

Simpson Bay Princess Juliana

Thu 3/5

1:29 pm-8:27 am

2 stops19h 58m

$567

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 2/26

4:20 pm-2:19 pm

2 stops20h 59m

Simpson Bay Princess Juliana

Thu 3/5

3:21 pm-8:27 am

1 stop18h 06m

$577

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 7/5

8:02 pm-3:31 pm

2 stops19h 29m

Simpson Bay Princess Juliana

Sun 7/12

2:45 pm-8:34 am

1 stop17h 49m

$579

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 7/5

8:02 pm-12:45 pm

2 stops16h 43m

Simpson Bay Princess Juliana

Sun 7/12

2:45 pm-8:34 am

1 stop17h 49m

$589

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 2/26

4:20 pm-12:29 pm

2 stops19h 09m

Simpson Bay Princess Juliana

Thu 3/5

1:29 pm-8:27 am

2 stops19h 58m

$607

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Charlottesville to Simpson Bay

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 airlines fly to Simpson Bay?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Simpson Bay from Charlottesville according to our data. American Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

When to book flights from Charlottesville to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Charlottesville to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Charlottesville to Simpson Bay (CHO to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charlottesville to Simpson Bay

Fastest flight time

6h 03m

Direct flights

None
The fastest flight from Charlottesville to Simpson Bay takes 6h 03m
There are no direct flights from Charlottesville to Simpson Bay. There are no popular flight routes from Charlottesville to Simpson Bay.
Search flight deals

  • How far is Charlottesville Albemarle to Simpson Bay Princess Juliana by plane?

    The distance between Charlottesville Albemarle and Simpson Bay Princess Juliana is about 1662.6 mi. Flights usually cover this in 6h 03m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Charlottesville Albemarle Airport to Simpson Bay Princess Juliana Airport?

    Prices for flights from Charlottesville Albemarle Airport to Simpson Bay Princess Juliana Airport refresh daily.

  • How old do you have to be to fly from Charlottesville Albemarle Airport to Simpson Bay Princess Juliana Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Charlottesville Albemarle Airport to Simpson Bay Princess Juliana Airport.

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Charlottesville to Simpson Bay?

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

Can I find flights from Charlottesville to Simpson Bay with flexible booking policies on momondo?

momondo does allow users to show only those flights to Simpson Bay from Charlottesville which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Charlottesville to Simpson Bay?

momondo helps you find the best flight between Charlottesville and Simpson Bay by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are not ready to book a flight from Charlottesville to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
American Airlines
United Airlines
Delta
Spirit Airlines
JetBlue