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Cheap flights from Simpson Bay to Madison from $370

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Simpson Bay to Madison departing on 12/16. 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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0 bags

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Cheap round-trip flights

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United Airlines Logo
2:40 pm - 3:05 pmSXM-MSN
26h 25m1 stop
United Airlines Logo
5:26 pm - 3:57 pmMSN-SXM
20h 31m1 stop
$650United Airlines
Find Deal
Sat, Dec 27 - Fri, Jan 2
American Airlines Logo
3:28 pm - 9:30 amSXM-MSN
20h 02m2 stops
American Airlines Logo
8:10 pm - 2:26 pmMSN-SXM
16h 16m2 stops
$692American Airlines
Find Deal
Sat, Dec 27 - Fri, Jan 2
American Airlines Logo
2:35 pm - 9:18 pmSXM-MSN
7h 43m1 stop
American Airlines Logo
6:49 pm - 3:15 pmMSN-SXM
19h 26m2 stops
$702American Airlines
Find Deal
Thu, Apr 23 - Sun, Apr 26
Delta Logo
1:50 pm - 10:35 pmSXM-MSN
9h 45m1 stop
Delta Logo
5:45 am - 2:09 pmMSN-SXM
7h 24m1 stop
$879Delta
Find Deal
Thu, Apr 23 - Sun, Apr 26

United Airlines flights from Simpson Bay to Madison

Our best United Airlines deals on Simpson Bay to Madison flight tickets
United Airlines
Dec 27
SXM2:40 pmSimpson Bay Princess Juliana
26h 25m
1 stop
MSN3:05 pmMadison Truax Field
Jan 2
MSN5:26 pmMadison Truax Field
20h 31m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
$650
Find similar
United Airlines
Nov 8
SXM5:00 pmSimpson Bay Princess Juliana
19h 00m
2 stops
MSN10:00 amMadison Truax Field
Nov 15
MSN6:20 amMadison Truax Field
7h 37m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
$867
Find similar
United Airlines
Nov 8
SXM2:40 pmSimpson Bay Princess Juliana
25h 23m
1 stop
MSN2:03 pmMadison Truax Field
Nov 14
MSN5:38 pmMadison Truax Field
20h 19m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
$876
Find similar

American Airlines flights from Simpson Bay to Madison

Our best American Airlines deals on Simpson Bay to Madison flight tickets
American Airlines
Dec 27
SXM3:28 pmSimpson Bay Princess Juliana
20h 02m
2 stops
MSN9:30 amMadison Truax Field
Jan 2
MSN8:10 pmMadison Truax Field
16h 16m
2 stops
SXM2:26 pmSimpson Bay Princess Juliana
$692
Find similar
American Airlines
Apr 23
SXM2:35 pmSimpson Bay Princess Juliana
7h 43m
1 stop
MSN9:18 pmMadison Truax Field
Apr 26
MSN6:49 pmMadison Truax Field
19h 26m
2 stops
SXM3:15 pmSimpson Bay Princess Juliana
$702
Find similar
American Airlines
Nov 5
SXM5:24 pmSimpson Bay Princess Juliana
19h 16m
2 stops
MSN10:40 amMadison Truax Field
Nov 12
MSN5:00 amMadison Truax Field
9h 22m
2 stops
SXM4:22 pmSimpson Bay Princess Juliana
$912
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Madison 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 October 30, 2025.
Use the filters below to find and compare flights from Simpson Bay to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 12/27

2:40 pm-3:05 pm

1 stop26h 25m

Madison Truax Field

Fri 1/2

5:26 pm-3:57 pm

1 stop20h 31m

$650

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 12/27

3:28 pm-9:30 am

2 stops20h 02m

Madison Truax Field

Fri 1/2

8:10 pm-2:26 pm

2 stops16h 16m

$692

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 4/23

2:35 pm-9:18 pm

1 stop7h 43m

Madison Truax Field

Sun 4/26

6:49 pm-3:15 pm

2 stops19h 26m

$702

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 4/23

1:50 pm-10:35 pm

1 stop9h 45m

Madison Truax Field

Sun 4/26

5:45 am-2:09 pm

1 stop7h 24m

$879

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:26 pm

1 stop8h 33m

$370

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 12/17

2:51 pm-11:40 pm

1 stop10h 49m

$375

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Tue 12/16

5:25 pm-10:31 am

2 stops19h 06m

$379

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

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 airline that flies from Simpson Bay Princess Juliana to Madison Truax Field?

Delta and American Airlines are the most popular carriers operating from Simpson Bay Princess Juliana to Madison Truax Field

When to book flights from Simpson Bay to Madison

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

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

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

Direct flights

None
There are no direct flights from Simpson Bay to Madison. There are no popular flight routes from Simpson Bay to Madison.
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  • How far is Simpson Bay Princess Juliana to Madison Truax Field by plane?

    A flight from Simpson Bay Princess Juliana to Madison Truax Field will travel around 2310.5 mi. 7h 43m is a normal flight duration for this route.

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

    Prices for flights from Simpson Bay Princess Juliana Airport to Madison Truax Field Airport refresh daily.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Simpson Bay Princess Juliana Airport to Madison Truax Field Airport.

  • What documentation or ID do you need to fly to Madison Truax Field Airport?

    The travel and health documents you'll need for your trip to Madison Truax Field Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Madison Truax Field Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Wisconsin Dells
Baraboo
Middleton
Fitchburg
Portage
Sun Prairie
Cambridge
Oxford
Windsor
Evansville

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Simpson Bay to Madison for you.

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

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

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

momondo helps you find the best flight between Simpson Bay and Madison by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Simpson Bay to Madison flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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