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Cheap flights from Madison to Simpson Bay from $503

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 4/11. 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
3:01 pm - 11:37 am
MSN
-
SXM
19h 36m
2 stops
American Airlines Logo
3:32 pm - 11:56 pm
SXM
-
MSN
9h 24m
1 stop
$503American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
11:35 am - 1:21 pm
MSN
-
SXM
24h 46m
1 stop
American Airlines Logo
3:32 pm - 11:56 pm
SXM
-
MSN
9h 24m
1 stop
$507American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
3:01 pm - 11:37 am
MSN
-
SXM
19h 36m
2 stops
American Airlines Logo
3:32 pm - 8:45 am
SXM
-
MSN
18h 13m
2 stops
$547American Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
11:35 am - 1:21 pm
MSN
-
SXM
24h 46m
1 stop
American Airlines Logo
3:32 pm - 11:56 pm
SXM
-
MSN
9h 24m
1 stop
$551American Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
11:35 am - 1:21 pm
MSN
-
SXM
24h 46m
1 stop
American Airlines Logo
4:35 pm - 11:05 am
SXM
-
MSN
19h 30m
2 stops
$556American Airlines
Mon, Apr 13 - Mon, Apr 20
American Airlines Logo
5:08 pm - 11:37 am
MSN
-
SXM
17h 29m
2 stops
American Airlines Logo
3:32 pm - 11:56 pm
SXM
-
MSN
9h 24m
1 stop
$564American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
11:35 am - 1:21 pm
MSN
-
SXM
24h 46m
1 stop
American Airlines Logo
3:32 pm - 11:56 pm
SXM
-
MSN
9h 24m
1 stop
$568American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
5:37 pm - 1:21 pm
MSN
-
SXM
18h 44m
2 stops
American Airlines Logo
4:35 pm - 10:55 am
SXM
-
MSN
19h 20m
2 stops
$630American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
5:08 pm - 1:21 pm
MSN
-
SXM
19h 13m
1 stop
American Airlines Logo
3:32 pm - 11:56 pm
SXM
-
MSN
9h 24m
1 stop
$635American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
5:52 pm - 12:43 pm
MSN
-
SXM
17h 51m
1 stop
American Airlines Logo
1:45 pm - 9:35 pm
SXM
-
MSN
8h 50m
1 stop
$650American Airlines
Wed, May 27 - Sun, May 31

Delta flights from Madison to Simpson Bay

Our best Delta deals on Madison to Simpson Bay flight tickets
Delta
Mar 12
MSN5:30 amMadison Truax Field
7h 24m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
Mar 18
SXM12:55 pmSimpson Bay Princess Juliana
10h 39m
1 stop
MSN10:34 pmMadison Truax Field
$810
Delta
Mar 12
MSN5:30 amMadison Truax Field
7h 24m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
Mar 17
SXM12:55 pmSimpson Bay Princess Juliana
20h 56m
2 stops
MSN8:51 amMadison Truax Field
$815
Delta
Mar 20
MSN6:28 pmMadison Truax Field
19h 40m
2 stops
SXM3:08 pmSimpson Bay Princess Juliana
Mar 26
SXM12:55 pmSimpson Bay Princess Juliana
22h 36m
1 stop
MSN10:31 amMadison Truax Field
$1,009

American Airlines flights from Madison to Simpson Bay

Our best American Airlines deals on Madison to Simpson Bay flight tickets
American Airlines
Apr 11
MSN3:01 pmMadison Truax Field
19h 36m
2 stops
SXM11:37 amSimpson Bay Princess Juliana
Apr 18
SXM3:32 pmSimpson Bay Princess Juliana
9h 24m
1 stop
MSN11:56 pmMadison Truax Field
$503
American Airlines
Apr 11
MSN11:35 amMadison Truax Field
24h 46m
1 stop
SXM1:21 pmSimpson Bay Princess Juliana
Apr 18
SXM3:32 pmSimpson Bay Princess Juliana
9h 24m
1 stop
MSN11:56 pmMadison Truax Field
$507
American Airlines
Apr 25
MSN3:01 pmMadison Truax Field
19h 36m
2 stops
SXM11:37 amSimpson Bay Princess Juliana
May 2
SXM3:32 pmSimpson Bay Princess Juliana
18h 13m
2 stops
MSN8:45 amMadison Truax Field
$547

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 March 2, 2026.
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

Sat 4/11

3:01 pm-11:37 am

2 stops19h 36m

Simpson Bay Princess Juliana

Sat 4/18

3:32 pm-11:56 pm

1 stop9h 24m

$503

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/11

11:35 am-1:21 pm

1 stop24h 46m

Simpson Bay Princess Juliana

Sat 4/18

3:32 pm-11:56 pm

1 stop9h 24m

$507

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/25

3:01 pm-11:37 am

2 stops19h 36m

Simpson Bay Princess Juliana

Sat 5/2

3:32 pm-8:45 am

2 stops18h 13m

$547

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/25

11:35 am-1:21 pm

1 stop24h 46m

Simpson Bay Princess Juliana

Sat 5/2

3:32 pm-11:56 pm

1 stop9h 24m

$551

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 4/13

11:35 am-1:21 pm

1 stop24h 46m

Simpson Bay Princess Juliana

Mon 4/20

4:35 pm-11:05 am

2 stops19h 30m

$556

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/11

5:08 pm-11:37 am

2 stops17h 29m

Simpson Bay Princess Juliana

Sat 4/18

3:32 pm-11:56 pm

1 stop9h 24m

$564

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/11

11:35 am-1:21 pm

1 stop24h 46m

Simpson Bay Princess Juliana

Sat 4/18

3:32 pm-11:56 pm

1 stop9h 24m

$568

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/11

5:37 pm-1:21 pm

2 stops18h 44m

Simpson Bay Princess Juliana

Sat 4/18

4:35 pm-10:55 am

2 stops19h 20m

$630

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/11

5:08 pm-1:21 pm

1 stop19h 13m

Simpson Bay Princess Juliana

Sat 4/18

3:32 pm-11:56 pm

1 stop9h 24m

$635

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 5/27

5:52 pm-12:43 pm

1 stop17h 51m

Simpson Bay Princess Juliana

Sun 5/31

1:45 pm-9:35 pm

1 stop8h 50m

$650

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

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

9h 19m

Direct flights

None
The fastest flight from Madison to Simpson Bay takes 9h 19m
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 9h 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 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.

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.

An easier way to manage your Simpson Bay trip

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