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Cheap flights from Madison to Simpson Bay from $617

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 10/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to Simpson Bay

Cheap round-trip flights

American Airlines Logo
5:46 pm - 3:15 pmMSN-SXM
20h 29m2 stops
American Airlines Logo
2:40 pm - 11:25 amSXM-MSN
21h 45m2 stops
$617American Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
American Airlines Logo
4:20 pm - 3:40 pmMSN-SXM
21h 20m2 stops
American Airlines Logo
4:45 pm - 10:18 amSXM-MSN
19h 33m2 stops
$642American Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
American Airlines Logo
10:35 am - 1:55 pmMSN-SXM
25h 20m1 stop
American Airlines Logo
4:45 pm - 10:43 amSXM-MSN
19h 58m2 stops
$652American Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
American Airlines Logo
10:35 am - 1:55 pmMSN-SXM
25h 20m1 stop
American Airlines Logo
3:35 pm - 11:41 pmSXM-MSN
10h 06m1 stop
$684American Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
Delta Logo
5:30 am - 1:49 pmMSN-SXM
7h 19m1 stop
Delta Logo
3:14 pm - 10:45 pmSXM-MSN
8h 31m1 stop
$772Delta
Find Deal
Wed, Oct 15 - Wed, Oct 22
American Airlines Logo
6:29 pm - 4:15 pmMSN-SXM
19h 46m2 stops
American Airlines Logo
3:30 pm - 10:28 amSXM-MSN
20h 58m2 stops
$1,217American Airlines
Find Deal
Thu, Dec 25 - Fri, Jan 2
American Airlines Logo
6:29 pm - 12:10 pmMSN-SXM
15h 41m1 stop
American Airlines Logo
3:30 pm - 9:23 pmSXM-MSN
7h 53m1 stop
$1,273American Airlines
Find Deal
Fri, Dec 26 - Sun, Jan 4
American Airlines Logo
5:11 pm - 12:10 pmMSN-SXM
16h 59m2 stops
American Airlines Logo
3:30 pm - 9:23 pmSXM-MSN
7h 53m1 stop
$1,278American Airlines
Find Deal
Fri, Dec 26 - Sun, Jan 4
American Airlines Logo
6:29 pm - 4:15 pmMSN-SXM
19h 46m2 stops
American Airlines Logo
3:30 pm - 9:23 pmSXM-MSN
7h 53m1 stop
$1,342American Airlines
Find Deal
Thu, Dec 25 - Fri, Jan 2
American Airlines Logo
5:20 pm - 12:10 pmMSN-SXM
16h 50m2 stops
American Airlines Logo
3:30 pm - 10:18 amSXM-MSN
20h 48m2 stops
$1,378American Airlines
Find Deal
Fri, Dec 26 - Sun, Jan 4

American Airlines flights from Madison to Simpson Bay

Our best American Airlines deals on Madison to Simpson Bay flight tickets
American Airlines
Oct 15
MSN5:46 pmMadison Truax Field
20h 29m
2 stops
SXM3:15 pmSimpson Bay Princess Juliana
Oct 22
SXM2:40 pmSimpson Bay Princess Juliana
21h 45m
2 stops
MSN11:25 amMadison Truax Field
$617
Find similar
American Airlines
Dec 11
MSN4:20 pmMadison Truax Field
21h 20m
2 stops
SXM3:40 pmSimpson Bay Princess Juliana
Dec 15
SXM4:45 pmSimpson Bay Princess Juliana
19h 33m
2 stops
MSN10:18 amMadison Truax Field
$642
Find similar
American Airlines
Dec 11
MSN10:35 amMadison Truax Field
25h 20m
1 stop
SXM1:55 pmSimpson Bay Princess Juliana
Dec 15
SXM4:45 pmSimpson Bay Princess Juliana
19h 58m
2 stops
MSN10:43 amMadison Truax Field
$652
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Madison to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 10/15

5:46 pm-3:15 pm

2 stops20h 29m

Simpson Bay Princess Juliana

Wed 10/22

2:40 pm-11:25 am

2 stops21h 45m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

4:20 pm-3:40 pm

2 stops21h 20m

Simpson Bay Princess Juliana

Mon 12/15

4:45 pm-10:18 am

2 stops19h 33m

$642

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

10:35 am-1:55 pm

1 stop25h 20m

Simpson Bay Princess Juliana

Mon 12/15

4:45 pm-10:43 am

2 stops19h 58m

$652

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

10:35 am-1:55 pm

1 stop25h 20m

Simpson Bay Princess Juliana

Mon 12/15

3:35 pm-11:41 pm

1 stop10h 06m

$684

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 10/15

5:30 am-1:49 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Wed 10/22

3:14 pm-10:45 pm

1 stop8h 31m

$772

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/25

6:29 pm-4:15 pm

2 stops19h 46m

Simpson Bay Princess Juliana

Fri 1/2

3:30 pm-10:28 am

2 stops20h 58m

$1,217

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 12/26

6:29 pm-12:10 pm

1 stop15h 41m

Simpson Bay Princess Juliana

Sun 1/4

3:30 pm-9:23 pm

1 stop7h 53m

$1,273

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 12/26

5:11 pm-12:10 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Sun 1/4

3:30 pm-9:23 pm

1 stop7h 53m

$1,278

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/25

6:29 pm-4:15 pm

2 stops19h 46m

Simpson Bay Princess Juliana

Fri 1/2

3:30 pm-9:23 pm

1 stop7h 53m

$1,342

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 12/26

5:20 pm-12:10 pm

2 stops16h 50m

Simpson Bay Princess Juliana

Sun 1/4

3:30 pm-10:18 am

2 stops20h 48m

$1,378

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Simpson Bay from

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 is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Wednesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $644. Flights from Madison to Simpson Bay on a Thursday will generally be more expensive and average around $940. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is in the afternoon. momondo users have found flights departing from Madison to Simpson Bay in the afternoon for as low as $719. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the evening when prices are around $1,229.

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

Direct flights

None
There are no direct flights from Madison to Simpson Bay. There are no popular flight routes from Madison to Simpson Bay.
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  • 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 19m 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?

  • 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?

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
DeltaPriceFrom $587Free CancellationRating
7.9
7,982 reviews
Search Delta flights
American AirlinesPriceFrom $647Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Simpson Bay?

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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