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Simpson Bay

$335+ Cheap flights from Charlottesville (CHO) to Simpson Bay (SXM)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 3/27:57 pm
CHO
-
SXM
1 stop17h 19m
American Airlines
Fri 3/2712:29 pm
SXM
-
CHO
2 stops19h 58m
American Airlines
Deal found 1/27$335
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 3/148:29 pm
CHO
-
SXM
2 stops15h 49m
United Airlines
Sat 3/214:00 pm
SXM
-
CHO
2 stops18h 09m
United Airlines
Deal found 1/27$505
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 2/264:20 pm
CHO
-
SXM
2 stops20h 59m
American Airlines
Thu 3/53:17 pm
SXM
-
CHO
2 stops18h 10m
American Airlines
Deal found 1/27$510
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 7/56:15 pm
CHO
-
SXM
2 stops19h 07m
American Airlines
Sun 7/121:45 pm
SXM
-
CHO
2 stops18h 49m
American Airlines
Deal found 1/27$534
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/92:41 pm
CHO
-
SXM
2 stops22h 09m
United Airlines
Fri 2/132:52 pm
SXM
-
CHO
2 stops28h 55m
United Airlines
Deal found 1/26$593
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Sun 2/82:41 pm
CHO
-
SXM
2 stops22h 09m
United Airlines
Thu 2/122:52 pm
SXM
-
CHO
2 stops24h 07m
United Airlines
Deal found 1/28$651

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(American 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
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 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

Mon 3/2

5:00 pm-2:19 pm

2 stops20h 19m

Simpson Bay Princess Juliana

Fri 3/27

12:29 pm-8:27 am

2 stops19h 58m

$335

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 3/14

8:29 pm-12:18 pm

2 stops15h 49m

Simpson Bay Princess Juliana

Sat 3/21

4:00 pm-10:09 am

2 stops18h 09m

$505

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

3:17 pm-8:27 am

2 stops18h 10m

$510

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 7/5

6:15 pm-1:22 pm

2 stops19h 07m

Simpson Bay Princess Juliana

Sun 7/12

1:45 pm-8:34 am

2 stops18h 49m

$534

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 2/9

2:41 pm-1:50 pm

2 stops22h 09m

Simpson Bay Princess Juliana

Fri 2/13

2:52 pm-6:47 pm

2 stops28h 55m

$593

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sun 2/8

2:41 pm-1:50 pm

2 stops22h 09m

Simpson Bay Princess Juliana

Thu 2/12

2:52 pm-1:59 pm

2 stops24h 07m

$651

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

  • 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 15h 49m. American Airlines provides one of the quickest options available for as low as $505. Airlines will cover a distance of 1668 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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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