MSN - SXM

$541 Find Cheap Flights from Madison to Simpson Bay - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$541
Typical prices: $753-$1,118
American Airlines
Wed 1/10Fri 1/19
MSN - SXM • 2 stops
Nonstop flights
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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Top layover airports
Cheapest • Avg $757 (round-trip)
Shortest trip • 8h 43m (one-way)
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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 10 - Tue, Jan 19
American Airlines Logo
5:37 pm - 2:28 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
18h 51m2 stops Dallas/Fort Worth Miami
American Airlines Logo
4:02 pm - 11:24 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
9h 22m1 stop Charlotte Douglas
$541American Airlines
Sun, Jan 10 - Tue, Jan 19
American Airlines Logo
6:33 pm - 2:59 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
18h 26m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
5:29 pm - 12:19 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
20h 50m2 stops Miami Charlotte Douglas
$541American Airlines
Sun, Jan 10 - Tue, Jan 19
American Airlines Logo
12:59 pm - 2:59 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
24h 00m1 stop Charlotte Douglas
American Airlines Logo
4:02 pm - 11:24 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
9h 22m1 stop Charlotte Douglas
$545American Airlines
Sat, Feb 6 - Thu, Feb 11
American Airlines Logo
5:10 pm - 2:59 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
19h 49m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
4:04 pm - 11:52 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
9h 48m1 stop Charlotte Douglas
$581American Airlines
Sat, Feb 6 - Thu, Feb 11
American Airlines Logo
5:10 pm - 4:26 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
21h 16m2 stops Chicago O'Hare Intl Miami
American Airlines Logo
1:39 pm - 12:12 amSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
12h 33m2 stops Miami Chicago O'Hare Intl
$581American Airlines
Tue, Feb 2 - Sun, Feb 7
American Airlines Logo
4:31 pm - 2:59 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
20h 28m2 stops Dallas/Fort Worth Charlotte Douglas
American Airlines Logo
1:34 pm - 12:14 amSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
12h 40m2 stops Miami Chicago O'Hare Intl
$586American Airlines
Tue, Feb 2 - Sun, Feb 7
American Airlines Logo
12:59 pm - 12:34 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
21h 35m2 stops Charlotte Douglas Miami
American Airlines Logo
5:29 pm - 12:19 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
20h 50m2 stops Miami Charlotte Douglas
$586American Airlines
Sat, Feb 6 - Thu, Feb 11
American Airlines Logo
12:59 pm - 2:59 pmMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
24h 00m1 stop Charlotte Douglas
American Airlines Logo
4:04 pm - 11:52 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
9h 48m1 stop Charlotte Douglas
$586American Airlines
Sat, Mar 27 - Tue, Mar 30
Delta Logo
11:00 am - 11:30 amMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
23h 30m2 stops Minneapolis St Paul New York John F Kennedy Intl
Delta Logo
3:20 pm - 4:37 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
26h 17m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County
$743Delta
Tue, Mar 23 - Tue, Mar 30
Delta Logo
11:00 am - 11:30 amMSN  Madison Truax Field-SXM Simpson Bay Princess Juliana
23h 30m2 stops Minneapolis St Paul New York John F Kennedy Intl
Delta Logo
3:20 pm - 4:37 pmSXM  Simpson Bay Princess Juliana-MSN Madison Truax Field
26h 17m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County
$743Delta
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 with more confidence.

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

Round-trip flights from Madison to Simpson Bay typically range from $753 to $1,118. The lowest price found in the past 5 days was $541, on American Airlines.

Key details for Madison to Simpson Bay flights

Cheapest flight

$541
Round-trip flight from Madison to Simpson Bay

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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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.

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

    A nonstop flight from Madison to Simpson Bay takes 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.

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

    Round-trip flights from Madison to Simpson Bay range from $753 to $1,118, with an average of $934 over the past 12 months. Anything below $753 counts as a good deal.

  • 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 $541 to $3,313. That means the highest observed fare was about 6x higher than the lowest one.

  • 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 averaging $40 for economy cars. Top options include:

    • Right Cars
    • Ace
    • Budget
    • Europcar
    • Alamo

  • 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).

  • 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) - 33% of one-stop connections
    • Charlotte Douglas (CLT) - 33% of one-stop connections
    • Philadelphia (PHL) - 25% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 8% of one-stop connections

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

    Yes. Flexible dates can save you up to 54% on flights from Madison to Simpson Bay. Friday is the cheapest departure day at $726 round-trip on average, while Saturday is the most expensive at $1,562, a difference of $836.

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

    Flying via Chicago O'Hare Intl (ORD) gives the shortest average 1-stop total travel time at 8h 43m, compared with 8h 54m via Atlanta Hartsfield-Jackson (ATL) and 13h 19m via Philadelphia (PHL).

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

    Simpson Bay is 2 hours ahead of Madison (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

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

Complete your trip to Simpson Bay with a hotel stay or car rental