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Cheap flights from Charlottesville to Simpson Bay from $356

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 8/14. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
5:16 pm - 3:39 pm
CHO
-
SXM
22h 23m
2 stops
American Airlines Logo
2:22 pm - 11:58 am
SXM
-
CHO
21h 36m
2 stops
$356American Airlines
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
12:36 pm - 1:33 pm
CHO
-
SXM
24h 57m
1 stop
American Airlines Logo
2:22 pm - 11:58 am
SXM
-
CHO
21h 36m
2 stops
$362American Airlines
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
6:03 pm - 4:20 pm
CHO
-
SXM
21h 17m
2 stops
American Airlines Logo
3:20 pm - 10:27 am
SXM
-
CHO
20h 07m
2 stops
$382American Airlines
Thu, Nov 26 - Thu, Dec 3
Delta Logo
6:00 am - 2:45 pm
CHO
-
SXM
7h 45m
1 stop
Delta Logo
4:10 pm - 10:49 pm
SXM
-
CHO
7h 39m
1 stop
$427Delta
Thu, Nov 26 - Thu, Dec 3
American Airlines Logo
6:08 pm - 3:39 pm
CHO
-
SXM
21h 31m
2 stops
American Airlines Logo
4:39 pm - 10:32 am
SXM
-
CHO
17h 53m
2 stops
$462American Airlines
Sat, Oct 24 - Fri, Oct 30
American Airlines Logo
6:08 pm - 3:39 pm
CHO
-
SXM
21h 31m
2 stops
American Airlines Logo
5:24 pm - 10:25 am
SXM
-
CHO
18h 01m
2 stops
$467American Airlines
Sat, Oct 24 - Sun, Nov 1
American Airlines Logo
8:04 pm - 3:39 pm
CHO
-
SXM
19h 35m
2 stops
American Airlines Logo
2:51 pm - 8:30 am
SXM
-
CHO
18h 39m
1 stop
$473American Airlines
Sat, Oct 24 - Sun, Nov 1
American Airlines Logo
12:36 pm - 1:33 pm
CHO
-
SXM
24h 57m
1 stop
American Airlines Logo
2:42 pm - 9:50 am
SXM
-
CHO
19h 08m
1 stop
$502American Airlines
Fri, Aug 14 - Fri, Aug 21
United Airlines Logo
7:59 pm - 12:50 pm
CHO
-
SXM
40h 51m
2 stops
United Airlines Logo
1:10 pm - 10:56 am
SXM
-
CHO
21h 46m
2 stops
$508United Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
8:04 pm - 3:39 pm
CHO
-
SXM
19h 35m
2 stops
American Airlines Logo
2:23 pm - 10:32 am
SXM
-
CHO
20h 09m
2 stops
$516American Airlines
Sat, Oct 17 - Sat, Oct 24

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Delta flights from Charlottesville to Simpson Bay

Our best Delta deals on Charlottesville to Simpson Bay flight tickets
Delta
Nov 26
CHO6:00 amCharlottesville Albemarle
7h 45m
1 stop
SXM2:45 pmSimpson Bay Princess Juliana
Dec 3
SXM4:10 pmSimpson Bay Princess Juliana
7h 39m
1 stop
CHO10:49 pmCharlottesville Albemarle
$427
Delta
Oct 24
CHO5:31 pmCharlottesville Albemarle
20h 18m
1 stop
SXM1:49 pmSimpson Bay Princess Juliana
Oct 30
SXM3:14 pmSimpson Bay Princess Juliana
8h 23m
1 stop
CHO11:37 pmCharlottesville Albemarle
$725
Delta
Aug 15
CHO7:10 amCharlottesville Albemarle
6h 43m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Aug 19
SXM3:18 pmSimpson Bay Princess Juliana
8h 17m
1 stop
CHO11:35 pmCharlottesville Albemarle
$935

American Airlines flights from Charlottesville to Simpson Bay

Our best American Airlines deals on Charlottesville to Simpson Bay flight tickets
American Airlines
Aug 14
CHO5:16 pmCharlottesville Albemarle
22h 23m
2 stops
SXM3:39 pmSimpson Bay Princess Juliana
Aug 21
SXM2:22 pmSimpson Bay Princess Juliana
21h 36m
2 stops
CHO11:58 amCharlottesville Albemarle
$356
American Airlines
Aug 14
CHO12:36 pmCharlottesville Albemarle
24h 57m
1 stop
SXM1:33 pmSimpson Bay Princess Juliana
Aug 21
SXM2:22 pmSimpson Bay Princess Juliana
21h 36m
2 stops
CHO11:58 amCharlottesville Albemarle
$362
American Airlines
Nov 26
CHO6:03 pmCharlottesville Albemarle
21h 17m
2 stops
SXM4:20 pmSimpson Bay Princess Juliana
Dec 3
SXM3:20 pmSimpson Bay Princess Juliana
20h 07m
2 stops
CHO10:27 amCharlottesville Albemarle
$382

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 July 4, 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

Cheapest round-trip

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 8/14

5:16 pm-3:39 pm

2 stops22h 23m

Simpson Bay Princess Juliana

Fri 8/21

2:22 pm-11:58 am

2 stops21h 36m

$356

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 8/14

12:36 pm-1:33 pm

1 stop24h 57m

Simpson Bay Princess Juliana

Fri 8/21

2:22 pm-11:58 am

2 stops21h 36m

$362

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 11/26

6:03 pm-4:20 pm

2 stops21h 17m

Simpson Bay Princess Juliana

Thu 12/3

3:20 pm-10:27 am

2 stops20h 07m

$382
Quickest round-trip

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Thu 11/26

6:00 am-2:45 pm

1 stop7h 45m

Simpson Bay Princess Juliana

Thu 12/3

4:10 pm-10:49 pm

1 stop7h 39m

$427

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 10/24

6:08 pm-3:39 pm

2 stops21h 31m

Simpson Bay Princess Juliana

Fri 10/30

4:39 pm-10:32 am

2 stops17h 53m

$462

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 10/24

6:08 pm-3:39 pm

2 stops21h 31m

Simpson Bay Princess Juliana

Sun 11/1

5:24 pm-10:25 am

2 stops18h 01m

$467

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 10/24

8:04 pm-3:39 pm

2 stops19h 35m

Simpson Bay Princess Juliana

Sun 11/1

2:51 pm-8:30 am

1 stop18h 39m

$473

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 8/14

12:36 pm-1:33 pm

1 stop24h 57m

Simpson Bay Princess Juliana

Fri 8/21

2:42 pm-9:50 am

1 stop19h 08m

$502

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 10/24

7:59 pm-12:50 pm

2 stops40h 51m

Simpson Bay Princess Juliana

Sat 10/31

1:10 pm-10:56 am

2 stops21h 46m

$508

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 10/17

8:04 pm-3:39 pm

2 stops19h 35m

Simpson Bay Princess Juliana

Sat 10/24

2:23 pm-10:32 am

2 stops20h 09m

$516

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 JetBlue 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 44% 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 08m

Direct flights

None
The fastest flight from Charlottesville to Simpson Bay takes 6h 08m
There are no direct flights from Charlottesville to Simpson Bay. There are no popular flight routes from Charlottesville to Simpson Bay.
Search flight deals

Frequently asked questions about flying from Charlottesville to Simpson Bay

  • 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 08m, 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
7.1
11,767 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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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
American Airlines
United Airlines
JetBlue
Delta
Southwest