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CHO - SXM

Find cheap flights from Charlottesville to Simpson Bay from $419

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charlottesville to Simpson Bay departing on 9/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/3
Mon 6/10

Search hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charlottesville to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charlottesville to Simpson Bay, as well as popular online travel agencies
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Charlottesville to Simpson Bay (CHO-SXM)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Charlottesville to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 1:49 pmCHO-SXM
7h 49m1 stop
3:19 pm - 4:08 pmSXM-CHO
24h 49m2 stops
$419Delta
Find Deal
Mon, Sep 23 - Wed, Sep 25
6:00 am - 1:49 pmCHO-SXM
7h 49m1 stop
3:19 pm - 11:33 amSXM-CHO
20h 14m1 stop
$422Delta
Find Deal
Mon, Sep 23 - Wed, Sep 25
8:25 pm - 1:22 pmCHO-SXM
16h 57m2 stops
2:42 pm - 8:33 amSXM-CHO
41h 51m2 stops
$514American Airlines
Find Deal
Mon, Sep 23 - Wed, Sep 25
8:25 pm - 1:22 pmCHO-SXM
16h 57m2 stops
2:42 pm - 1:10 pmSXM-CHO
22h 28m2 stops
$516American Airlines
Find Deal
Mon, Sep 23 - Wed, Sep 25

Good to know

Low season

May

High season

January

Cheapest flight

$419
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Charlottesville to Simpson Bay

When to book flights from Charlottesville to Simpson Bay

Are your dates flexible? Find out the best times to travel from Charlottesville to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Charlottesville to Simpson Bay

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

    In the last 3 days, the lowest price for a flight from Charlottesville to Simpson Bay was $419 for a round-trip ticket.

  • Do I need a passport to fly between Charlottesville and Simpson Bay?

    Yes, you’ll need a passport to travel to Simpson Bay from Charlottesville.

  • Which aircraft models fly most regularly from Charlottesville to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Charlottesville to Simpson Bay?

    SkyTeam, and oneworld are the airline alliances operating flights between Charlottesville and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Charlottesville to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Charlottesville to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Charlottesville to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Charlottesville is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Charlottesville to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Charlottesville with another airline. Booking your flights between Charlottesville and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Charlottesville to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Charlottesville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Charlottesville to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Charlottesville to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Charlottesville to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
American AirlinesOverall score based on 14728 reviews
6.6Food
7.6Boarding
7.1Entertainment
8.0Crew
7.2Comfort
Airline reviews

I was in business class. There was an excellent headset. But half an hour before arrival they collected them! The rest of the trip I had to use a cheap earphone. There must be a better way to protect the headphones.

8.0 ExcellentMehdi, May 2024JFK - MXP
Read more about American Airlines reviews

I was in business class. There was an excellent headset. But half an hour before arrival they collected them! The rest of the trip I had to use a cheap earphone. There must be a better way to protect the headphones.

All four American Airlines flights I took in last seven days were delayed. Caused me loads of problems, missed meetings, loss of time and money.

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Not being able to purchase my check in baggage online was a negative.

LATE LATE LATE!!! Plagued by late AA flights on this trip. Such a drag. This one was by far the worst.

WiFi connected but only let you go to the AA website, not even text messaging worked.

Too bad that first class seats do not recline significantly causing discomfort

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Charlottesville - Simpson Bay Flights

Departure:

Charlottesville (CHO)United States

Destination:

Simpson Bay (SXM)St. Maarten

Cabin classes: