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Cheap flights from Madison to Simpson Bay from $536

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 2/11. 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

Enter your travel dates to find the best prices.
American Airlines Logo
4:30 pm - 12:38 pm
MSN
-
SXM
18h 08m2 stops
American Airlines Logo
3:20 pm - 9:13 am
SXM
-
MSN
19h 53m2 stops
$536American Airlines
Wed, Feb 11 - Wed, Feb 25
American Airlines Logo
3:09 pm - 12:58 pm
MSN
-
SXM
19h 49m2 stops
American Airlines Logo
5:33 pm - 10:55 am
SXM
-
MSN
19h 22m2 stops
$561American Airlines
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
5:51 pm - 12:58 pm
MSN
-
SXM
17h 07m2 stops
American Airlines Logo
3:23 pm - 11:40 pm
SXM
-
MSN
10h 17m1 stop
$566American Airlines
Fri, Jan 23 - Sat, Jan 31
American Airlines Logo
4:47 pm - 2:31 pm
MSN
-
SXM
19h 44m1 stop
American Airlines Logo
4:24 pm - 11:41 pm
SXM
-
MSN
9h 17m1 stop
$567American Airlines
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
3:57 pm - 12:38 pm
MSN
-
SXM
18h 41m2 stops
American Airlines Logo
5:28 pm - 10:15 am
SXM
-
MSN
18h 47m2 stops
$571American Airlines
Wed, Feb 11 - Sun, Feb 15
United Airlines Logo
12:57 pm - 1:50 pm
MSN
-
SXM
22h 53m2 stops
United Airlines Logo
1:52 pm - 10:37 pm
SXM
-
MSN
9h 45m1 stop
$587United Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
3:09 pm - 1:42 pm
MSN
-
SXM
20h 33m2 stops
American Airlines Logo
5:28 pm - 9:13 am
SXM
-
MSN
17h 45m2 stops
$601American Airlines
Sat, Feb 7 - Sat, Feb 21
United Airlines Logo
12:57 pm - 1:50 pm
MSN
-
SXM
22h 53m2 stops
United Airlines Logo
3:55 pm - 2:02 pm
SXM
-
MSN
23h 07m2 stops
$607United Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
4:30 pm - 1:42 pm
MSN
-
SXM
19h 12m1 stop
American Airlines Logo
5:28 pm - 10:10 am
SXM
-
MSN
18h 42m2 stops
$610American Airlines
Sat, Feb 7 - Sat, Feb 21
United Airlines Logo
6:00 am - 3:51 pm
MSN
-
SXM
7h 51m1 stop
United Airlines Logo
2:52 pm - 11:44 pm
SXM
-
MSN
10h 52m1 stop
$611United Airlines
Sun, Jan 25 - Wed, Jan 28

United Airlines flights from Madison to Simpson Bay

Our best United Airlines deals on Madison to Simpson Bay flight tickets
United Airlines
Mar 4
MSN12:57 pmMadison Truax Field
22h 53m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Mar 11
SXM1:52 pmSimpson Bay Princess Juliana
9h 45m
1 stop
MSN10:37 pmMadison Truax Field
$587
Find similar
United Airlines
Mar 4
MSN12:57 pmMadison Truax Field
22h 53m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Mar 11
SXM3:55 pmSimpson Bay Princess Juliana
23h 07m
2 stops
MSN2:02 pmMadison Truax Field
$607
Find similar
United Airlines
Jan 25
MSN6:00 amMadison Truax Field
7h 51m
1 stop
SXM3:51 pmSimpson Bay Princess Juliana
Jan 28
SXM2:52 pmSimpson Bay Princess Juliana
10h 52m
1 stop
MSN11:44 pmMadison Truax Field
$611
Find similar

American Airlines flights from Madison to Simpson Bay

Our best American Airlines deals on Madison to Simpson Bay flight tickets
American Airlines
Feb 11
MSN4:30 pmMadison Truax Field
18h 08m
2 stops
SXM12:38 pmSimpson Bay Princess Juliana
Feb 25
SXM3:20 pmSimpson Bay Princess Juliana
19h 53m
2 stops
MSN9:13 amMadison Truax Field
$536
Find similar
American Airlines
Jan 15
MSN3:09 pmMadison Truax Field
19h 49m
2 stops
SXM12:58 pmSimpson Bay Princess Juliana
Jan 22
SXM5:33 pmSimpson Bay Princess Juliana
19h 22m
2 stops
MSN10:55 amMadison Truax Field
$561
Find similar
American Airlines
Jan 23
MSN5:51 pmMadison Truax Field
17h 07m
2 stops
SXM12:58 pmSimpson Bay Princess Juliana
Jan 31
SXM3:23 pmSimpson Bay Princess Juliana
10h 17m
1 stop
MSN11:40 pmMadison Truax Field
$566
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 December 11, 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 2/11

4:30 pm-12:38 pm

2 stops18h 08m

Simpson Bay Princess Juliana

Wed 2/25

3:20 pm-9:13 am

2 stops19h 53m

$536

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 1/15

3:09 pm-12:58 pm

2 stops19h 49m

Simpson Bay Princess Juliana

Thu 1/22

5:33 pm-10:55 am

2 stops19h 22m

$561

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 1/23

5:51 pm-12:58 pm

2 stops17h 07m

Simpson Bay Princess Juliana

Sat 1/31

3:23 pm-11:40 pm

1 stop10h 17m

$566

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 1/15

4:47 pm-2:31 pm

1 stop19h 44m

Simpson Bay Princess Juliana

Thu 1/22

4:24 pm-11:41 pm

1 stop9h 17m

$567

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 2/11

3:57 pm-12:38 pm

2 stops18h 41m

Simpson Bay Princess Juliana

Sun 2/15

5:28 pm-10:15 am

2 stops18h 47m

$571

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 3/4

12:57 pm-1:50 pm

2 stops22h 53m

Simpson Bay Princess Juliana

Wed 3/11

1:52 pm-10:37 pm

1 stop9h 45m

$587

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 2/7

3:09 pm-1:42 pm

2 stops20h 33m

Simpson Bay Princess Juliana

Sat 2/21

5:28 pm-9:13 am

2 stops17h 45m

$601

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 3/4

12:57 pm-1:50 pm

2 stops22h 53m

Simpson Bay Princess Juliana

Wed 3/11

3:55 pm-2:02 pm

2 stops23h 07m

$607

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 2/7

4:30 pm-1:42 pm

1 stop19h 12m

Simpson Bay Princess Juliana

Sat 2/21

5:28 pm-10:10 am

2 stops18h 42m

$610

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 1/25

6:00 am-3:51 pm

1 stop7h 51m

Simpson Bay Princess Juliana

Wed 1/28

2:52 pm-11:44 pm

1 stop10h 52m

$611

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.

Can stopping save me money on Madison to Simpson Bay flights?

You could potentially save up to 39% on your flight if you consider stops on a Madison to Simpson Bay flight.

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

Fastest flight time

6h 50m

Direct flights

None
The fastest flight from Madison to Simpson Bay takes 6h 50m
There are no direct flights from Madison to Simpson Bay. There are no popular flight routes from Madison to Simpson Bay.
Search flight deals

  • 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 6h 50m 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
8,007 reviews
Search Delta 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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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
Delta
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