MSN - SXM

$566 Find Cheap Flights from Madison to Simpson Bay - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$566
Typical prices: $759-$997
Delta
Wed 1/24Sun 1/28
MSN - SXM • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Madison and Simpson Bay. You'll need to take a connecting flight to reach the destination.
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Insights
Top layover airports
Philadelphia (PHL)
Cheapest • Avg $757 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 8h 34m (one-way)
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Insights
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Flight Deals

Cheap Flights from Madison to Simpson Bay (MSN-SXM)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Simpson Bay

Sun, Jan 24 - Thu, Jan 28
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Mon, Jan 25 - Fri, Jan 29
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Sun, Jan 24 - Fri, Jan 29
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Mon, Jan 25 - Thu, Jan 28
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Sun, Jan 24 - Thu, Jan 28
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Sun, Jan 24 - Fri, Jan 29
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Mon, Jan 25 - Fri, Jan 29
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Mon, Jan 25 - Thu, Jan 28
Delta Logo
5:45 am - 2:40 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:34 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 54m1 stop Atlanta Hartsfield-Jackson
$566Delta
Sat, Feb 6 - Thu, Feb 11
American Airlines Logo
9:04 pm - 2:57 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
15h 53m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
3:19 pm - 8:06 amSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
18h 47m2 stops Miami Chicago O'Hare Intl
$571American Airlines
Sat, Feb 6 - Thu, Feb 11
American Airlines Logo
3:38 pm - 2:57 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
21h 19m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
3:20 pm - 11:45 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
10h 25m1 stop Charlotte Douglas
$571American Airlines
Booking Insights

Price, demand and travel trends for Madison to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Madison to Simpson Bay with more confidence.

How much is a round-trip flight from Madison to Simpson Bay?

Round-trip flights from Madison to Simpson Bay start at $566. Prices are below average for this route right now, with typical round-trip fares ranging from $759 to $997. The lowest price found in the past 5 days was $566 on Delta.

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When to book flights from Madison to Simpson Bay

Are your dates flexible? Find out the best times to travel from Madison 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

Your Madison to Simpson Bay flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Madison to Simpson Bay?

    Flights from Madison to Simpson Bay usually depart from Madison Truax Field (MSN) and arrive at Simpson Bay Princess Juliana (SXM).

  • What cabin classes can I book on flights from Madison to Simpson Bay?

    Only Economy Class is available on flights from Madison to Simpson Bay.

  • Which airports do connecting flights from Madison to Simpson Bay pass through?

    One-stop flights from Madison to Simpson Bay most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 43% of one-stop connections
    • Philadelphia (PHL) - 43% of one-stop connections
    • Charlotte Douglas (CLT) - 14% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Madison to Simpson Bay?

    Yes. Being flexible with your travel dates can save you up to 52% on the Madison to Simpson Bay route. Friday is the cheapest departure day at $726 round-trip on average, while Saturday is the most expensive at $1,499, a difference of $773. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Madison to Simpson Bay?

    A nonstop flight from Madison to Simpson Bay takes 0h 00m, covering 2,311 miles.

  • Do I need a passport to fly from Madison to Simpson Bay?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Madison to Simpson Bay changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $566 to $2,493. That means the highest observed fare was about 4x higher than the lowest one.

  • How much time can I save by choosing a different layover airport from Madison to Simpson Bay?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 8h 34m, compared with 13h 19m via Philadelphia (PHL) and 15h 02m via Charlotte Douglas (CLT).

  • What is the time difference between Madison and Simpson Bay?

    Simpson Bay is 1 hour ahead of Madison (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
    • Ace
    • Right Cars
    • Europcar
    • Budget
    • Alamo

  • How much should I expect to pay for a Madison to Simpson Bay flight?

    Round-trip flights from Madison to Simpson Bay range from $759 to $997, with an average of $934 over the past 12 months. Anything below $759 counts as a good deal.

Your guide to booking Madison to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.

More options for your flight from Madison to Simpson Bay

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