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Simpson Bay

$671+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — SXM
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$671
(American Airlines)
From Charlottesville Albemarle to Simpson Bay Princess Juliana
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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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/12. 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 12/86:05 amCHO - SXM
1 stop6h 47mAmerican Airlines
Fri 12/122:51 pmSXM - CHO
1 stop9h 42mAmerican Airlines
Deal found 9/12$671
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/86:05 amCHO - SXM
1 stop6h 47mAmerican Airlines
Wed 12/102:51 pmSXM - CHO
1 stop20h 36mAmerican Airlines
Deal found 9/14$679
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 12/207:57 pmCHO - SXM
2 stops19h 36mAmerican Airlines
Tue 12/305:33 pmSXM - CHO
2 stops22h 22mAmerican Airlines
Deal found 9/13$846
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 10/106:01 pmCHO - SXM
2 stops21h 14mAmerican Airlines
Wed 10/152:40 pmSXM - CHO
2 stops19h 51mAmerican Airlines
Deal found 9/13$848
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 12/207:57 pmCHO - SXM
2 stops19h 36mAmerican Airlines
Sat 12/275:33 pmSXM - CHO
2 stops20h 31mAmerican Airlines
Deal found 9/13$936
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 12/196:10 amCHO - SXM
1 stop6h 40mUnited Airlines
Sat 12/275:00 pmSXM - CHO
2 stops18h 15mUnited Airlines
Deal found 9/13$997
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 12/196:01 pmCHO - SXM
2 stops17h 31mAmerican Airlines
Sat 12/275:33 pmSXM - CHO
2 stops20h 31mAmerican Airlines
Deal found 9/13$1,110

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 September 15, 2025.
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 12/8

6:05 am-1:52 pm

1 stop6h 47m

Simpson Bay Princess Juliana

Fri 12/12

2:51 pm-11:33 pm

1 stop9h 42m

$671

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Mon 12/8

6:05 am-1:52 pm

1 stop6h 47m

Simpson Bay Princess Juliana

Wed 12/10

5:25 pm-1:14 pm

2 stops20h 49m

$676

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Fri 10/10

6:01 pm-3:15 pm

2 stops21h 14m

Simpson Bay Princess Juliana

Wed 10/15

2:40 pm-10:31 am

2 stops19h 51m

$848

CharlottesvilleSimpson Bay

CHO - SXM

CHOSXM

Charlottesville Albemarle

Sat 12/20

7:57 pm-4:33 pm

2 stops19h 36m

Simpson Bay Princess Juliana

Sat 12/27

5:33 pm-1:04 pm

2 stops20h 31m

$936

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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, September is the cheapest month in which you can book a flight from Charlottesville to Simpson Bay (average of $459). Flying from Charlottesville to Simpson Bay in March is currently the most expensive (average of $652). 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.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Charlottesville to Simpson Bay, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 47m. American Airlines provides one of the quickest options available for as low as $671. Airlines will cover a distance of 1668 mi.

  • What is the cheapest airline to fly from Charlottesville to Simpson Bay round-trip?

    Our cheapest airline available from Charlottesville to Simpson Bay is American Airlines. Our recent data shows that you can find tickets from as low as $562 on this airline.

  • 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, September is the cheapest month in which you can book a flight from Charlottesville to Simpson Bay (average of $459). Flying from Charlottesville to Simpson Bay in March is currently the most expensive (average of $652). 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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Top airline flying from Charlottesville to Simpson Bay

Discover the top airline that operate flights from Charlottesville to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$562Average$774FlexibilityNo cancel feeOn-time71%

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