CHO - SXM

$356 Find Cheap Flights from Charlottesville to Simpson Bay - Compare and Save

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 7/19. 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
1 adult, Economy, 0 bags

KAYAK searches 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
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Everything you should know

Cheapest round-trip
$356
American Airlines
Sun 7/19Wed 7/22
CHO - SXM • 2 stops
Top airlines
Cheapest • from $356 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Charlottesville and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $847 (round-trip)
Shortest trip • 6h 44m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Charlottesville to Simpson Bay

Sun, Jul 19 - Wed, Jul 22
American Airlines Logo
8:00 pm - 3:44 pm
CHO
-
SXM
19h 44m
2 stops
American Airlines Logo
1:34 pm - 8:34 am
SXM
-
CHO
19h 00m
2 stops
$356American Airlines
Sun, Jul 19 - Wed, Jul 22
American Airlines Logo
8:00 pm - 1:51 pm
CHO
-
SXM
17h 51m
1 stop
American Airlines Logo
1:34 pm - 8:34 am
SXM
-
CHO
19h 00m
2 stops
$362American Airlines
Sun, Jul 19 - Wed, Jul 22
American Airlines Logo
8:00 pm - 1:51 pm
CHO
-
SXM
17h 51m
1 stop
American Airlines Logo
2:51 pm - 10:11 pm
SXM
-
CHO
7h 20m
1 stop
$494American Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
6:08 pm - 3:05 pm
CHO
-
SXM
20h 57m
2 stops
American Airlines Logo
2:50 pm - 9:30 am
SXM
-
CHO
18h 40m
2 stops
$506American Airlines
Sat, Oct 24 - Sat, Oct 31
United Airlines Logo
7:59 pm - 12:50 pm
CHO
-
SXM
40h 51m
2 stops
United Airlines Logo
4:00 pm - 11:32 pm
SXM
-
CHO
7h 32m
1 stop
$508United Airlines
Sun, Sep 6 - Sat, Sep 12
American Airlines Logo
6:49 am - 1:32 pm
CHO
-
SXM
6h 43m
1 stop
American Airlines Logo
2:53 pm - 8:30 am
SXM
-
CHO
17h 37m
1 stop
$511American Airlines
Mon, Oct 26 - Sat, Oct 31
United Airlines Logo
7:55 pm - 12:50 pm
CHO
-
SXM
16h 55m
2 stops
United Airlines Logo
4:00 pm - 10:58 am
SXM
-
CHO
18h 58m
2 stops
$512United Airlines
Sun, Sep 6 - Sat, Sep 12
American Airlines Logo
6:15 pm - 1:22 pm
CHO
-
SXM
19h 07m
2 stops
American Airlines Logo
2:53 pm - 8:30 am
SXM
-
CHO
17h 37m
1 stop
$516American Airlines
Mon, Oct 26 - Mon, Nov 2
United Airlines Logo
7:55 pm - 12:50 pm
CHO
-
SXM
16h 55m
2 stops
United Airlines Logo
2:52 pm - 9:56 am
SXM
-
CHO
20h 04m
2 stops
$542United Airlines
Sat, Aug 8 - Sat, Aug 15
American Airlines Logo
7:21 pm - 3:39 pm
CHO
-
SXM
20h 18m
2 stops
American Airlines Logo
2:33 pm - 8:35 am
SXM
-
CHO
18h 02m
1 stop
$546American Airlines
Booking Insights

KAYAK's insights & trends for Charlottesville to Simpson Bay flights

Get data-powered insights and trends into flights from Charlottesville to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Charlottesville to Simpson Bay?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Charlottesville to Simpson Bay were found on American Airlines ($356) and United Airlines ($508).

Good to know

Cheapest flight$356
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 5 days, the lowest price for a flight from Charlottesville to Simpson Bay was $356 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?

    oneworld is the only airline alliance operating flights between Charlottesville and Simpson Bay.

  • 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.

Reviews of the 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.
7.1
American AirlinesOverall score based on 11774 reviews
7.9Crew
6.4Food
7.2Comfort
7.5Boarding
6.8Entertainment
Airline reviews

They did not offer coffee on a 7am flight…awful!!

6.0 GoodNan, Jun 2026
RIC - CLT
Read more American Airlines reviews

They did not offer coffee on a 7am flight…awful!!

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

The flight took off an hour late which made the connection concerning

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

Never had such a lazy first class attendant. Literally spent 60%+ of the flight playing games on her personal phone making up excuses of why she was unavailable.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

The flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

No explanation of why there was no snack and drink service (unless requested) when there was service in the other direction.

Baggage claim took too long and priority bags were not delivered first.

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

Information on your arrival and departure airports