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Simpson Bay

$98+ Cheap flights from Charlottesville (CHO) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SXM
helmi 17 — helmi 241
ti 2/17
ti 2/24
1 adult, Economy
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Cheap flight deals from Charlottesville to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Charlottesville (CHO) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated tammikuu 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$290
(United Airlines)

One-way from

$98
(United Airlines)

Popular in

May

Cheapest in

January

Average price

$562
Provider with most accurate pricing for Charlottesville Albemarle-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Charlottesville Albemarle-Simpson Bay Princess Juliana flights.
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From Charlottesville Albemarle to Simpson Bay Princess Juliana
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One-way flight from Charlottesville Albemarle to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 7% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($56 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Charlottesville to Simpson Bay

Cheapest flights from Charlottesville to Simpson Bay
Explore the most affordable flight options available from Charlottesville to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on tammikuu 18, 2026.

This United Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 3/238:29 pm
CHO
-
SXM
1 stop16h 21m
United Airlines
ma 3/303:50 pm
SXM
-
CHO
2 stops18h 20m
United Airlines
Deal found 1/17$290
This United Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/246:20 am
CHO
-
SXM
1 stop6h 30m
United Airlines
ti 3/313:50 pm
SXM
-
CHO
1 stop18h 08m
United Airlines
Deal found 1/17$291
This American Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/245:30 pm
CHO
-
SXM
2 stops21h 58m
American Airlines
ma 3/302:17 pm
SXM
-
CHO
2 stops19h 30m
American Airlines
Deal found 1/17$316
This United Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/246:20 am
CHO
-
SXM
1 stop6h 30m
United Airlines
ke 4/13:50 pm
SXM
-
CHO
1 stop18h 08m
United Airlines
Deal found 1/17$333
This American Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/247:17 pm
CHO
-
SXM
2 stops20h 11m
American Airlines
ke 4/112:29 pm
SXM
-
CHO
2 stops19h 58m
American Airlines
Deal found 1/17$335
This United Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ke 3/256:20 am
CHO
-
SXM
1 stop6h 30m
United Airlines
ke 4/11:35 pm
SXM
-
CHO
2 stops20h 23m
United Airlines
Deal found 1/17$382
This United Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 2/92:41 pm
CHO
-
SXM
2 stops22h 09m
United Airlines
pe 2/132:52 pm
SXM
-
CHO
2 stops33h 07m
United Airlines
Deal found 1/17$446
This American Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to 2/267:57 pm
CHO
-
SXM
2 stops19h 03m
American Airlines
to 3/53:21 pm
SXM
-
CHO
1 stop9h 34m
American Airlines
Deal found 1/17$471
This United Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 1/262:41 pm
CHO
-
SXM
2 stops22h 09m
United Airlines
to 1/292:52 pm
SXM
-
CHO
2 stops23h 50m
United Airlines
Deal found 1/16$546

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated tammikuu 18, 2026.
Use the filters below to find and compare flights from Charlottesville to Simpson Bay that are best for you.

Fly from

Charlottesville

Fly to

Simpson Bay

Route

Depart

Return

Price

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ti 3/24

6:20 am-12:50 pm

1 stop6h 30m

Simpson Bay Princess Juliana

ma 3/30

3:50 pm-10:10 am

2 stops18h 20m

$290

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ma 3/23

8:29 pm-12:50 pm

1 stop16h 21m

Simpson Bay Princess Juliana

ma 3/30

3:50 pm-10:10 am

2 stops18h 20m

$290

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ke 3/25

6:20 am-12:50 pm

1 stop6h 30m

Simpson Bay Princess Juliana

ti 3/31

3:50 pm-9:58 am

1 stop18h 08m

$291

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ti 3/24

6:20 am-12:50 pm

1 stop6h 30m

Simpson Bay Princess Juliana

ti 3/31

3:50 pm-9:58 am

1 stop18h 08m

$291

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ma 3/30

6:20 am-12:33 pm

1 stop6h 13m

Simpson Bay Princess Juliana

ti 3/31

3:50 pm-1:53 pm

1 stop22h 03m

$291

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ti 3/24

5:30 pm-11:29 am

2 stops17h 59m

Simpson Bay Princess Juliana

ti 3/31

4:28 pm-4:31 pm

2 stops24h 03m

$316

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ke 3/25

7:57 pm-3:28 pm

2 stops19h 31m

Simpson Bay Princess Juliana

ti 3/31

2:17 pm-8:27 am

2 stops18h 10m

$316

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

to 2/26

7:57 pm-4:00 pm

2 stops19h 03m

Simpson Bay Princess Juliana

to 3/5

3:17 pm-8:27 am

2 stops18h 10m

$316

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

ti 3/24

5:30 pm-3:28 pm

2 stops21h 58m

Simpson Bay Princess Juliana

ma 3/30

2:17 pm-9:47 am

2 stops19h 30m

$316

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

su 3/8

6:20 am-12:50 pm

1 stop6h 30m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/17

Showing 1-10 of 16 results
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  • Most accurate provider: When it comes to deals on Charlottesville-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charlottesville-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charlottesville-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Charlottesville-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Charlottesville-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Charlottesville to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Charlottesville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Charlottesville to Simpson Bay

What is the cheapest month to book a flight from Charlottesville to Simpson Bay?

Currently, March is the cheapest month in which you can book a flight from Charlottesville to Simpson Bay (average of $214). Flying from Charlottesville to Simpson Bay in April is currently the most expensive (average of $477). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Charlottesville to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Charlottesville to Simpson Bay?

    A quick flight from Charlottesville to Simpson Bay can take about 6h 30m. United Airlines provides one of the quickest options available for as low as $290. Airlines will cover a distance of 1668 mi.

  • Can I find deals for flights from Charlottesville to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Charlottesville to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Charlottesville to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Charlottesville to Simpson Bay.

  • Can I find deals for business class flights from Charlottesville to Simpson Bay?

    Yes. Cheapflights offers flight deals from Charlottesville to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Charlottesville to Simpson Bay?

    Currently, March is the cheapest month in which you can book a flight from Charlottesville to Simpson Bay (average of $214). Flying from Charlottesville to Simpson Bay in April is currently the most expensive (average of $477). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Simpson Bay?

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

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