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Cheap flights from Charlottesville to Simpson Bay from $298

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 1/24. 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

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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
7:09 pm - 4:28 pm
CHO
-
SXM
20h 19m2 stops
American Airlines Logo
5:33 pm - 11:58 am
SXM
-
CHO
19h 25m2 stops
$298American Airlines
Sat, Jan 24 - Fri, Jan 30
American Airlines Logo
7:09 pm - 1:42 pm
CHO
-
SXM
17h 33m1 stop
American Airlines Logo
5:33 pm - 11:58 am
SXM
-
CHO
19h 25m2 stops
$304American Airlines
Sat, Jan 24 - Fri, Jan 30
American Airlines Logo
6:00 am - 4:28 pm
CHO
-
SXM
9h 28m2 stops
American Airlines Logo
3:31 pm - 11:58 am
SXM
-
CHO
21h 27m2 stops
$346American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
6:00 am - 1:45 pm
CHO
-
SXM
6h 45m1 stop
American Airlines Logo
5:01 pm - 11:58 am
SXM
-
CHO
19h 57m1 stop
$348American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
7:09 pm - 4:28 pm
CHO
-
SXM
20h 19m2 stops
American Airlines Logo
5:01 pm - 9:59 am
SXM
-
CHO
17h 58m1 stop
$352American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
10:24 am - 1:45 pm
CHO
-
SXM
26h 21m1 stop
American Airlines Logo
5:01 pm - 9:59 am
SXM
-
CHO
17h 58m1 stop
$354American Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
7:09 pm - 1:42 pm
CHO
-
SXM
17h 33m1 stop
American Airlines Logo
4:24 pm - 11:19 pm
SXM
-
CHO
7h 55m1 stop
$404American Airlines
Sat, Jan 24 - Fri, Jan 30
United Airlines Logo
2:41 pm - 1:50 pm
CHO
-
SXM
22h 09m2 stops
United Airlines Logo
2:52 pm - 1:42 pm
SXM
-
CHO
23h 50m2 stops
$446United Airlines
Mon, Jan 26 - Fri, Jan 30
United Airlines Logo
2:41 pm - 1:50 pm
CHO
-
SXM
22h 09m2 stops
United Airlines Logo
2:52 pm - 1:42 pm
SXM
-
CHO
23h 50m2 stops
$496United Airlines
Mon, Jan 26 - Fri, Jan 30

American Airlines flights from Charlottesville to Simpson Bay

Our best American Airlines deals on Charlottesville to Simpson Bay flight tickets
American Airlines
Jan 24
CHO7:09 pmCharlottesville Albemarle
20h 19m
2 stops
SXM4:28 pmSimpson Bay Princess Juliana
Jan 30
SXM5:33 pmSimpson Bay Princess Juliana
19h 25m
2 stops
CHO11:58 amCharlottesville Albemarle
$298
Find similar
American Airlines
Jan 24
CHO7:09 pmCharlottesville Albemarle
17h 33m
1 stop
SXM1:42 pmSimpson Bay Princess Juliana
Jan 30
SXM5:33 pmSimpson Bay Princess Juliana
19h 25m
2 stops
CHO11:58 amCharlottesville Albemarle
$304
Find similar
American Airlines
Jan 20
CHO7:09 pmCharlottesville Albemarle
20h 19m
2 stops
SXM4:28 pmSimpson Bay Princess Juliana
Jan 24
SXM5:33 pmSimpson Bay Princess Juliana
19h 25m
2 stops
CHO11:58 amCharlottesville Albemarle
$346
Find similar

United Airlines flights from Charlottesville to Simpson Bay

Our best United Airlines deals on Charlottesville to Simpson Bay flight tickets
United Airlines
Jan 26
CHO2:41 pmCharlottesville Albemarle
22h 09m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Jan 30
SXM2:52 pmSimpson Bay Princess Juliana
23h 50m
2 stops
CHO1:42 pmCharlottesville Albemarle
$446
Find similar
United Airlines
Jan 26
CHO2:41 pmCharlottesville Albemarle
22h 09m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Jan 30
SXM2:52 pmSimpson Bay Princess Juliana
23h 50m
2 stops
CHO1:42 pmCharlottesville Albemarle
$496
Find similar

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 December 23, 2025.
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

Sat 1/24

7:09 pm-4:28 pm

2 stops20h 19m

Simpson Bay Princess Juliana

Fri 1/30

5:33 pm-11:58 am

2 stops19h 25m

$298

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 1/24

7:09 pm-1:42 pm

1 stop17h 33m

Simpson Bay Princess Juliana

Fri 1/30

5:33 pm-11:58 am

2 stops19h 25m

$304

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 1/20

6:00 am-4:28 pm

2 stops9h 28m

Simpson Bay Princess Juliana

Sat 1/24

3:31 pm-11:58 am

2 stops21h 27m

$346

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 1/20

6:00 am-1:45 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Sat 1/24

5:01 pm-11:58 am

1 stop19h 57m

$348

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 1/20

7:09 pm-4:28 pm

2 stops20h 19m

Simpson Bay Princess Juliana

Sat 1/24

5:01 pm-9:59 am

1 stop17h 58m

$352

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Tue 1/20

10:24 am-1:45 pm

1 stop26h 21m

Simpson Bay Princess Juliana

Sat 1/24

5:01 pm-9:59 am

1 stop17h 58m

$354

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 1/24

7:09 pm-1:42 pm

1 stop17h 33m

Simpson Bay Princess Juliana

Fri 1/30

4:24 pm-11:19 pm

1 stop7h 55m

$404

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 1/26

2:41 pm-1:50 pm

2 stops22h 09m

Simpson Bay Princess Juliana

Fri 1/30

2:52 pm-1:42 pm

2 stops23h 50m

$446

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 1/26

2:41 pm-1:50 pm

2 stops22h 09m

Simpson Bay Princess Juliana

Fri 1/30

2:52 pm-1:42 pm

2 stops23h 50m

$496

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 is the typical price of a round-trip flight between Charlottesville and Simpson Bay?

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Friday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $704. Flights from Charlottesville to Simpson Bay on a Saturday will generally be more expensive and average around $1,082. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

22h 09m

Direct flights

None
The fastest flight from Charlottesville to Simpson Bay takes 22h 09m
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 22h 09m, 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 many operators does momondo search for flights from Charlottesville Albemarle Airport to Simpson Bay Princess Juliana Airport?

  • 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.

  • What is the most popular airline from Charlottesville to Simpson Bay?

Best airlines flying from Charlottesville to Simpson Bay

Compare and see reviews for airlines that fly from Charlottesville to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $562Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights

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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