When did momondo last update prices for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport?

Prices for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport were last updated today.

How many operators does momondo search for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport?

As of October 2026, there is 1 operator available to choose from for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport.

How old do you have to be to fly from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$497 Cheap Flights from Madison to Simpson Bay in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Simpson Bay

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5:45 pm - 2:59 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

19h 14m2 stops Dallas/Fort Worth Charlotte Douglas

4:02 pm - 8:38 amSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

18h 36m2 stops Charlotte Douglas Chicago O'Hare Intl

$497American Airlines

Thu, Jan 21 - Tue, Jan 26

5:00 am - 3:07 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

8h 07m1 stop Chicago O'Hare Intl

5:22 pm - 10:54 amSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

19h 32m2 stops Miami Chicago O'Hare Intl

$497American Airlines

Sat, Feb 6 - Thu, Feb 11

4:01 pm - 4:26 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

22h 25m2 stops Chicago O'Hare Intl Miami

5:22 pm - 10:54 amSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

19h 32m2 stops Miami Chicago O'Hare Intl

$497American Airlines

Sat, Feb 6 - Thu, Feb 11

4:01 pm - 4:26 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

22h 25m2 stops Chicago O'Hare Intl Miami

3:44 pm - 8:18 amSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

18h 34m2 stops Charlotte Douglas Chicago O'Hare Intl

$497American Airlines

Sat, Feb 6 - Thu, Feb 11

5:45 pm - 2:59 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

19h 14m2 stops Dallas/Fort Worth Charlotte Douglas

4:02 pm - 11:24 pmSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

9h 22m1 stop Charlotte Douglas

$497American Airlines

Thu, Jan 21 - Tue, Jan 26

4:31 pm - 2:59 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

20h 28m2 stops Dallas/Fort Worth Charlotte Douglas

5:29 pm - 12:04 pmSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

20h 35m2 stops Miami Washington, D.C. Reagan-National

$502American Airlines

Tue, Feb 2 - Sun, Feb 7

7:03 pm - 2:28 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

17h 25m2 stops Chicago O'Hare Intl Miami

5:29 pm - 11:00 amSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

19h 31m2 stops Miami Chicago O'Hare Intl

$502American Airlines

Tue, Feb 2 - Sun, Feb 7

12:59 pm - 12:34 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

21h 35m2 stops Charlotte Douglas Miami

5:29 pm - 12:19 pmSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

20h 50m2 stops Miami Charlotte Douglas

$522American Airlines

Tue, Feb 2 - Sun, Feb 7

8:15 am - 1:50 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

27h 35m2 stops Chicago O'Hare Intl Newark

2:52 pm - 11:37 pmSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

10h 45m1 stop Newark

$620United Airlines

Sun, Nov 15 - Thu, Nov 19

8:15 am - 1:50 pmMSN Madison Truax Field-SXM Simpson Bay Princess Juliana

27h 35m2 stops Chicago O'Hare Intl Newark

2:52 pm - 5:54 pmSXM Simpson Bay Princess Juliana-MSN Madison Truax Field

29h 02m2 stops Newark Chicago O'Hare Intl

$620United Airlines

Sun, Nov 15 - Thu, Nov 19

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American Airlines flights from Madison to Simpson Bay

Our best American Airlines deals on Madison to Simpson Bay flight tickets

American Airlines

Feb 6

MSN5:00 amMadison Truax Field

8h 07m

1 stop

SXM3:07 pmSimpson Bay Princess Juliana

Feb 11

SXM5:22 pmSimpson Bay Princess Juliana

19h 32m

2 stops

MSN10:54 amMadison Truax Field

$497

American Airlines

Feb 2

MSN4:31 pmMadison Truax Field

20h 28m

2 stops

SXM2:59 pmSimpson Bay Princess Juliana

Feb 7

SXM5:29 pmSimpson Bay Princess Juliana

20h 35m

2 stops

MSN12:04 pmMadison Truax Field

$502

American Airlines

Feb 2

MSN12:59 pmMadison Truax Field

21h 35m

2 stops

SXM12:34 pmSimpson Bay Princess Juliana

Feb 7

SXM5:29 pmSimpson Bay Princess Juliana

20h 50m

2 stops

MSN12:19 pmMadison Truax Field

$522

United Airlines flights from Madison to Simpson Bay

Our best United Airlines deals on Madison to Simpson Bay flight tickets

United Airlines

Nov 15

MSN8:15 amMadison Truax Field

27h 35m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

Nov 19

SXM2:52 pmSimpson Bay Princess Juliana

10h 45m

1 stop

MSN11:37 pmMadison Truax Field

$620

United Airlines

Nov 15

MSN6:15 amMadison Truax Field

29h 35m

1 stop

SXM1:50 pmSimpson Bay Princess Juliana

Nov 19

SXM2:52 pmSimpson Bay Princess Juliana

10h 45m

1 stop

MSN11:37 pmMadison Truax Field

$626

United Airlines

Feb 6

MSN6:35 amMadison Truax Field

7h 22m

1 stop

SXM3:57 pmSimpson Bay Princess Juliana

Feb 11

SXM5:00 pmSimpson Bay Princess Juliana

31h 10m

2 stops

MSN10:10 pmMadison Truax Field

$627

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Thu 1/21

5:45 pm-2:59 pm

2 stops19h 14m

Simpson Bay Princess Juliana

Tue 1/26

4:02 pm-8:38 am

2 stops18h 36m

$497

Quickest round-trip

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Sat 2/6

5:00 am-3:07 pm

1 stop8h 07m

Simpson Bay Princess Juliana

Thu 2/11

5:22 pm-10:54 am

2 stops19h 32m

$497

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Sat 2/6

4:01 pm-4:26 pm

2 stops22h 25m

Simpson Bay Princess Juliana

Thu 2/11

5:22 pm-10:54 am

2 stops19h 32m

$497

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Sat 2/6

4:01 pm-4:26 pm

2 stops22h 25m

Simpson Bay Princess Juliana

Thu 2/11

3:44 pm-8:18 am

2 stops18h 34m

$497

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Thu 1/21

5:45 pm-2:59 pm

2 stops19h 14m

Simpson Bay Princess Juliana

Tue 1/26

4:02 pm-11:24 pm

1 stop9h 22m

$497

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Tue 2/2

4:31 pm-2:59 pm

2 stops20h 28m

Simpson Bay Princess Juliana

Sun 2/7

5:29 pm-12:04 pm

2 stops20h 35m

$502

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Tue 2/2

7:03 pm-2:28 pm

2 stops17h 25m

Simpson Bay Princess Juliana

Sun 2/7

5:29 pm-11:00 am

2 stops19h 31m

$502

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Tue 2/2

12:59 pm-12:34 pm

2 stops21h 35m

Simpson Bay Princess Juliana

Sun 2/7

5:29 pm-12:19 pm

2 stops20h 50m

$522

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Sun 11/15

8:15 am-1:50 pm

2 stops27h 35m

Simpson Bay Princess Juliana

Thu 11/19

2:52 pm-11:37 pm

1 stop10h 45m

$620

MadisonSimpson Bay

MSN Madison Truax Field - SXM Simpson Bay Princess Juliana

MSNSXM

Madison Truax Field

Sun 11/15

8:15 am-1:50 pm

2 stops27h 35m

Simpson Bay Princess Juliana

Thu 11/19

2:52 pm-5:54 pm

2 stops29h 02m

$620

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

How to get the cheapest flight ticket from Madison to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What airlines fly to Simpson Bay?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Simpson Bay from Madison according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 4 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

When to book flights from Madison to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Madison to Simpson Bay (MSN to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Simpson Bay

Best Price Found	$497
Fastest flight time	7h 39m
Direct flights	None

The best flight deal from Madison to Simpson Bay found on momondo in the last 72 hours is $497

The fastest flight from Madison to Simpson Bay takes 7h 39m

There are no direct flights from Madison to Simpson Bay. There are no popular flight routes from Madison to Simpson Bay.

Search flight deals

Frequently asked questions about flying from Madison to Simpson Bay

How far is Madison Truax Field to Simpson Bay Princess Juliana by plane?
Madison Truax Field and Simpson Bay Princess Juliana are 2310.5 mi apart from one another. Typically, this will take 7h 39m by plane in normal conditions.
When did momondo last update prices for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport were last updated today.
How many operators does momondo search for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport?
As of October 2026, there is 1 operator available to choose from for flights from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport.
How old do you have to be to fly from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Madison Truax Field Airport to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Madison to Simpson Bay?
Based on momondo bookings for flights between Madison and Simpson Bay, the leading airline is American Airlines, making up 100% of the total bookings.

Best airlines flying from Madison to Simpson Bay

Compare and see reviews for airlines that fly from Madison to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $559	Free Cancellation	Rating 7.0 12,193 reviews		Search American Airlines flights

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momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Madison to Simpson Bay. momondo saves you time and could save you money on your trip.

Can I find flights from Madison to Simpson Bay with flexible booking policies on momondo?

All flight searches from Madison to Simpson Bay on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Madison to Simpson Bay?

Once you have performed a search for Madison to Simpson Bay flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Madison to Simpson Bay right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Simpson Bay, momondo offers a useful price alert feature which will track prices for flights to Simpson Bay from Madison and alert you when they change.

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Cheap flights from Madison to Simpson Bay from $497

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Simpson Bay departing on 1/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Madison to Simpson Bay

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What airlines fly to Simpson Bay?

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Cheap Madison to Simpson Bay (MSN to SXM) flight deals and tips

Best Price Found

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Direct flights

Frequently asked questions about flying from Madison to Simpson Bay

Best airlines flying from Madison to Simpson Bay

Compare and see reviews for airlines that fly from Madison to Simpson Bay with momondo

Traveling to a place near Simpson Bay?

Why use momondo?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Simpson Bay

List of cabin classes available on flights landing in Simpson Bay. Availability may vary depending on flight origin and airline.

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