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Cheap flights from Simpson Bay to Madison from $494

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Simpson Bay to Madison departing on 11/25. 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 Simpson Bay to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
3:00 pm - 11:57 pm
SXM
-
MSN
10h 57m
1 stop
American Airlines Logo
6:38 pm - 4:25 pm
MSN
-
SXM
19h 47m
2 stops
$494American Airlines
Wed, Nov 25 - Tue, Dec 1
American Airlines Logo
3:00 pm - 11:57 pm
SXM
-
MSN
10h 57m
1 stop
American Airlines Logo
6:38 pm - 1:58 pm
MSN
-
SXM
17h 20m
1 stop
$606American Airlines
Wed, Nov 25 - Tue, Dec 1
American Airlines Logo
3:00 pm - 11:57 pm
SXM
-
MSN
10h 57m
1 stop
American Airlines Logo
6:38 pm - 1:57 pm
MSN
-
SXM
17h 19m
1 stop
$609American Airlines
Wed, Nov 25 - Sat, Nov 28
American Airlines Logo
5:33 pm - 11:50 am
SXM
-
MSN
20h 17m
2 stops
American Airlines Logo
6:38 pm - 1:57 pm
MSN
-
SXM
17h 19m
1 stop
$614American Airlines
Wed, Nov 25 - Sat, Nov 28
American Airlines Logo
5:33 pm - 11:57 pm
SXM
-
MSN
32h 24m
2 stops
American Airlines Logo
8:42 pm - 1:57 pm
MSN
-
SXM
15h 15m
2 stops
$623American Airlines
Tue, Nov 24 - Sat, Nov 28
American Airlines Logo
3:00 pm - 11:42 am
SXM
-
MSN
22h 42m
1 stop
American Airlines Logo
6:55 am - 1:57 pm
MSN
-
SXM
29h 02m
1 stop
$630American Airlines
Wed, Nov 25 - Sun, Nov 29
American Airlines Logo
5:33 pm - 11:57 pm
SXM
-
MSN
32h 24m
2 stops
American Airlines Logo
12:12 pm - 4:25 pm
MSN
-
SXM
26h 13m
2 stops
$633American Airlines
Tue, Nov 24 - Tue, Dec 1
American Airlines Logo
3:00 pm - 3:04 pm
SXM
-
MSN
26h 04m
2 stops
American Airlines Logo
6:55 am - 1:57 pm
MSN
-
SXM
29h 02m
1 stop
$640American Airlines
Wed, Nov 25 - Sun, Nov 29
American Airlines Logo
5:33 pm - 11:57 pm
SXM
-
MSN
32h 24m
2 stops
American Airlines Logo
6:55 am - 1:57 pm
MSN
-
SXM
29h 02m
1 stop
$643American Airlines
Tue, Nov 24 - Sun, Nov 29
United Airlines Logo
2:52 pm - 9:50 am
SXM
-
MSN
44h 58m
2 stops
United Airlines Logo
8:20 am - 3:57 pm
MSN
-
SXM
29h 37m
1 stop
$647United Airlines
Wed, Nov 25 - Fri, Dec 4

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American Airlines flights from Simpson Bay to Madison

Our best American Airlines deals on Simpson Bay to Madison flight tickets
American Airlines
Nov 25
SXM3:00 pmSimpson Bay Princess Juliana
10h 57m
1 stop
MSN11:57 pmMadison Truax Field
Dec 1
MSN6:38 pmMadison Truax Field
19h 47m
2 stops
SXM4:25 pmSimpson Bay Princess Juliana
$494
American Airlines
Nov 25
SXM3:00 pmSimpson Bay Princess Juliana
10h 57m
1 stop
MSN11:57 pmMadison Truax Field
Dec 1
MSN6:38 pmMadison Truax Field
17h 20m
1 stop
SXM1:58 pmSimpson Bay Princess Juliana
$606
American Airlines
Nov 25
SXM3:00 pmSimpson Bay Princess Juliana
10h 57m
1 stop
MSN11:57 pmMadison Truax Field
Nov 28
MSN6:38 pmMadison Truax Field
17h 19m
1 stop
SXM1:57 pmSimpson Bay Princess Juliana
$609

United Airlines flights from Simpson Bay to Madison

Our best United Airlines deals on Simpson Bay to Madison flight tickets
United Airlines
Nov 25
SXM2:52 pmSimpson Bay Princess Juliana
44h 58m
2 stops
MSN9:50 amMadison Truax Field
Dec 4
MSN8:20 amMadison Truax Field
29h 37m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
$647
United Airlines
Nov 24
SXM2:52 pmSimpson Bay Princess Juliana
10h 45m
1 stop
MSN11:37 pmMadison Truax Field
Dec 4
MSN8:20 amMadison Truax Field
29h 37m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
$678
United Airlines
Nov 26
SXM2:52 pmSimpson Bay Princess Juliana
32h 13m
2 stops
MSN9:05 pmMadison Truax Field
Dec 4
MSN8:20 amMadison Truax Field
29h 37m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
$688

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 July 31, 2026.
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

Cheapest round-trip

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 11/25

3:00 pm-11:57 pm

1 stop10h 57m

Madison Truax Field

Tue 12/1

6:38 pm-4:25 pm

2 stops19h 47m

$494

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 11/25

3:00 pm-11:57 pm

1 stop10h 57m

Madison Truax Field

Tue 12/1

6:38 pm-1:58 pm

1 stop17h 20m

$606
Quickest round-trip

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 11/25

3:00 pm-11:57 pm

1 stop10h 57m

Madison Truax Field

Sat 11/28

6:38 pm-1:57 pm

1 stop17h 19m

$609

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 11/25

5:33 pm-11:50 am

2 stops20h 17m

Madison Truax Field

Sat 11/28

6:38 pm-1:57 pm

1 stop17h 19m

$614

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Tue 11/24

5:33 pm-11:57 pm

2 stops32h 24m

Madison Truax Field

Sat 11/28

8:42 pm-1:57 pm

2 stops15h 15m

$623

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 11/25

3:00 pm-11:42 am

1 stop22h 42m

Madison Truax Field

Sun 11/29

6:55 am-1:57 pm

1 stop29h 02m

$630

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Tue 11/24

5:33 pm-11:57 pm

2 stops32h 24m

Madison Truax Field

Tue 12/1

12:12 pm-4:25 pm

2 stops26h 13m

$633

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 11/25

3:00 pm-3:04 pm

2 stops26h 04m

Madison Truax Field

Sun 11/29

6:55 am-1:57 pm

1 stop29h 02m

$640

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Tue 11/24

5:33 pm-11:57 pm

2 stops32h 24m

Madison Truax Field

Sun 11/29

6:55 am-1:57 pm

1 stop29h 02m

$643

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 11/25

2:52 pm-9:50 am

2 stops44h 58m

Madison Truax Field

Fri 12/4

8:20 am-3:57 pm

1 stop29h 37m

$647

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

Fastest flight time

23h 40m

Direct flights

None
The fastest flight from Simpson Bay to Madison takes 23h 40m
There are no direct flights from Simpson Bay to Madison. There are no popular flight routes from Simpson Bay to Madison.
Search flight deals

Frequently asked questions about flying from Simpson Bay to Madison

  • 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. 23h 40m 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.

Frequently asked questions about flying from Simpson Bay to Madison

  • How do I get Price Alerts for flights from Simpson Bay to Madison?

    Price Alerts will notify you by email when the price for flights to Madison from Simpson Bay decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

  • How can I save money on flights from Simpson Bay to Madison with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We compare prices from 700+ competitors to help you find the price that works best for you. momondo operates in over 30 international markets, bringing you access to a wide range of fares and deals. Search for your travel using momondo for a diverse range of options from airlines and OTAs.

Traveling to a place near Madison?

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

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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