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Cheap flights from Madison to Simpson Bay from $630

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 8/10. 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
1 adult, Economy, 0 bags

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
5:47 pm - 3:39 pm
MSN
-
SXM
20h 52m
2 stops
American Airlines Logo
4:39 pm - 12:43 pm
SXM
-
MSN
21h 04m
2 stops
$630American Airlines
Mon, Aug 10 - Fri, Aug 21
American Airlines Logo
5:00 am - 3:44 pm
MSN
-
SXM
9h 44m
2 stops
American Airlines Logo
2:51 pm - 11:42 pm
SXM
-
MSN
9h 51m
1 stop
$635American Airlines
Wed, Jul 22 - Wed, Jul 29
Delta Logo
5:48 am - 1:53 pm
MSN
-
SXM
7h 05m
1 stop
Delta Logo
3:18 pm - 10:43 pm
SXM
-
MSN
8h 25m
1 stop
$675Delta
Wed, Jul 1 - Fri, Jul 3
Delta Logo
5:45 pm - 1:53 pm
MSN
-
SXM
19h 08m
2 stops
Delta Logo
3:18 pm - 10:43 pm
SXM
-
MSN
8h 25m
1 stop
$680Delta
Mon, Jun 29 - Fri, Jul 3
American Airlines Logo
5:52 pm - 12:40 pm
MSN
-
SXM
17h 48m
1 stop
American Airlines Logo
2:51 pm - 11:42 pm
SXM
-
MSN
9h 51m
1 stop
$745American Airlines
Tue, Jun 30 - Tue, Jul 7
American Airlines Logo
6:42 pm - 1:22 pm
MSN
-
SXM
17h 40m
2 stops
American Airlines Logo
2:51 pm - 12:32 pm
SXM
-
MSN
22h 41m
2 stops
$750American Airlines
Mon, Jun 29 - Tue, Jul 7
Delta Logo
5:52 am - 1:53 pm
MSN
-
SXM
7h 01m
1 stop
Delta Logo
3:18 pm - 10:43 pm
SXM
-
MSN
8h 25m
1 stop
$755Delta
Mon, Jun 29 - Fri, Jul 3
Delta Logo
5:48 am - 1:53 pm
MSN
-
SXM
7h 05m
1 stop
Delta Logo
3:18 pm - 8:12 am
SXM
-
MSN
17h 54m
2 stops
$760Delta
Wed, Jul 1 - Sat, Jul 4
American Airlines Logo
5:52 pm - 3:42 pm
MSN
-
SXM
20h 50m
2 stops
American Airlines Logo
2:53 pm - 10:38 am
SXM
-
MSN
20h 45m
2 stops
$770American Airlines
Wed, Jun 24 - Sun, Jun 28
American Airlines Logo
5:52 pm - 12:40 pm
MSN
-
SXM
17h 48m
1 stop
American Airlines Logo
1:34 pm - 12:32 pm
SXM
-
MSN
23h 58m
2 stops
$775American Airlines
Tue, Jun 30 - Mon, Jul 6

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Delta flights from Madison to Simpson Bay

Our best Delta deals on Madison to Simpson Bay flight tickets
Delta
Jul 1
MSN5:48 amMadison Truax Field
7h 05m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Jul 3
SXM3:18 pmSimpson Bay Princess Juliana
8h 25m
1 stop
MSN10:43 pmMadison Truax Field
$675
Delta
Jun 29
MSN5:45 pmMadison Truax Field
19h 08m
2 stops
SXM1:53 pmSimpson Bay Princess Juliana
Jul 3
SXM3:18 pmSimpson Bay Princess Juliana
8h 25m
1 stop
MSN10:43 pmMadison Truax Field
$680
Delta
Jun 29
MSN5:52 amMadison Truax Field
7h 01m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Jul 3
SXM3:18 pmSimpson Bay Princess Juliana
8h 25m
1 stop
MSN10:43 pmMadison Truax Field
$755

American Airlines flights from Madison to Simpson Bay

Our best American Airlines deals on Madison to Simpson Bay flight tickets
American Airlines
Dec 5
MSN8:08 pmMadison Truax Field
18h 17m
2 stops
SXM4:25 pmSimpson Bay Princess Juliana
Dec 12
SXM3:20 pmSimpson Bay Princess Juliana
19h 59m
2 stops
MSN9:19 amMadison Truax Field
$563
American Airlines
Dec 5
MSN3:55 pmMadison Truax Field
20h 03m
1 stop
SXM1:58 pmSimpson Bay Princess Juliana
Dec 12
SXM3:20 pmSimpson Bay Princess Juliana
19h 59m
2 stops
MSN9:19 amMadison Truax Field
$571
American Airlines
Aug 10
MSN5:47 pmMadison Truax Field
20h 52m
2 stops
SXM3:39 pmSimpson Bay Princess Juliana
Aug 21
SXM4:39 pmSimpson Bay Princess Juliana
21h 04m
2 stops
MSN12:43 pmMadison Truax Field
$630

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 June 9, 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

Cheapest round-trip

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 8/10

5:47 pm-3:39 pm

2 stops20h 52m

Simpson Bay Princess Juliana

Fri 8/21

4:39 pm-12:43 pm

2 stops21h 04m

$630

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 7/22

5:00 am-3:44 pm

2 stops9h 44m

Simpson Bay Princess Juliana

Wed 7/29

2:51 pm-11:42 pm

1 stop9h 51m

$635

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 7/1

5:48 am-1:53 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Fri 7/3

3:18 pm-10:43 pm

1 stop8h 25m

$675

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 6/29

5:45 pm-1:53 pm

2 stops19h 08m

Simpson Bay Princess Juliana

Fri 7/3

3:18 pm-10:43 pm

1 stop8h 25m

$680

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/30

5:52 pm-12:40 pm

1 stop17h 48m

Simpson Bay Princess Juliana

Tue 7/7

2:51 pm-11:42 pm

1 stop9h 51m

$745

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 6/29

6:42 pm-1:22 pm

2 stops17h 40m

Simpson Bay Princess Juliana

Tue 7/7

2:51 pm-12:32 pm

2 stops22h 41m

$750
Quickest round-trip

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 6/29

5:52 am-1:53 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Fri 7/3

3:18 pm-10:43 pm

1 stop8h 25m

$755

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 7/1

5:48 am-1:53 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Sat 7/4

3:18 pm-8:12 am

2 stops17h 54m

$760

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 6/24

5:52 pm-3:42 pm

2 stops20h 50m

Simpson Bay Princess Juliana

Sun 6/28

2:53 pm-10:38 am

2 stops20h 45m

$770

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/30

5:52 pm-12:40 pm

1 stop17h 48m

Simpson Bay Princess Juliana

Mon 7/6

1:34 pm-12:32 pm

2 stops23h 58m

$775

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

7h 10m

Direct flights

None
The fastest flight from Madison to Simpson Bay takes 7h 10m
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 10m 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.

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Fly your favorite airline to Simpson Bay

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