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Cheap flights from Simpson Bay to Madison from $302

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 5/20. 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

Find the cheapest flights from Simpson Bay to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
3:50 pm - 9:59 am
SXM
-
MSN
19h 09m
2 stops
United Airlines Logo
7:17 pm - 12:33 pm
MSN
-
SXM
16h 16m
2 stops
$590United Airlines
Sat, Jun 13 - Sat, Jun 20
American Airlines Logo
2:22 pm - 7:45 am
SXM
-
MSN
18h 23m
2 stops
American Airlines Logo
7:00 am - 1:50 pm
MSN
-
SXM
29h 50m
1 stop
$649American Airlines
Sat, Jun 13 - Sat, Jun 20
American Airlines Logo
1:40 pm - 10:29 pm
SXM
-
MSN
9h 49m
1 stop
American Airlines Logo
7:00 am - 1:50 pm
MSN
-
SXM
29h 50m
1 stop
$744American Airlines
Sat, Jun 13 - Sat, Jun 20

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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
Jun 13
SXM2:22 pmSimpson Bay Princess Juliana
18h 23m
2 stops
MSN7:45 amMadison Truax Field
Jun 20
MSN7:00 amMadison Truax Field
29h 50m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
$649
American Airlines
Jun 13
SXM1:40 pmSimpson Bay Princess Juliana
9h 49m
1 stop
MSN10:29 pmMadison Truax Field
Jun 20
MSN7:00 amMadison Truax Field
29h 50m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
$744

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 May 1, 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
Quickest round-trip

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 6/13

3:50 pm-9:59 am

2 stops19h 09m

Madison Truax Field

Sat 6/20

7:17 pm-12:33 pm

2 stops16h 16m

$590

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 6/13

2:22 pm-7:45 am

2 stops18h 23m

Madison Truax Field

Sat 6/20

7:00 am-1:50 pm

1 stop29h 50m

$649

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 6/13

1:40 pm-10:29 pm

1 stop9h 49m

Madison Truax Field

Sat 6/20

7:00 am-1:50 pm

1 stop29h 50m

$744
Cheapest one-way
Quickest one-way

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 5/20

2:24 pm-11:54 pm

1 stop10h 30m

$302

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 5/20

4:35 pm-11:36 am

2 stops20h 01m

$307

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Wed 5/20

9:35 am-8:25 am

3 stops47h 50m

$452

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Madison from

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?

American Airlines is the most popular carrier 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

Fastest flight time

19h 09m

Direct flights

None
The fastest flight from Simpson Bay to Madison takes 19h 09m
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. 19h 09m 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
Sun Prairie
Middleton
Fitchburg
Portage
Windsor
Cambridge
Oxford
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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