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St. Maarten

$303+ Cheap flights from Madison (MSN) to St. Maarten

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Madison to St. Maarten

Cheapest flights from Madison to St. Maarten
Explore the most affordable flight options available from Madison to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:44 pm
MSN
-
SXM
1 stop18h 01m
American Airlines
Wed 6/241:45 pm
SXM
-
MSN
1 stop9h 28m
American Airlines
Deal found 1/27$615
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:25 pm
MSN
-
SXM
2 stops18h 55m
American Airlines
Sat 11/73:20 pm
SXM
-
MSN
2 stops20h 01m
American Airlines
Deal found 1/27$645
This American Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/194:51 pm
MSN
-
SXM
2 stops19h 25m
American Airlines
Sun 5/241:45 pm
SXM
-
MSN
1 stop9h 28m
American Airlines
Deal found 1/28$650
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:00 am
MSN
-
SXM
1 stop10h 49m
United Airlines
Wed 4/293:50 pm
SXM
-
MSN
2 stops19h 22m
United Airlines
Deal found 1/28$755
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/218:15 am
MSN
-
SXM
1 stop29h 42m
United Airlines
Mon 3/303:50 pm
SXM
-
MSN
2 stops20h 48m
United Airlines
Deal found 1/28$761
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/74:30 pm
MSN
-
SXM
2 stops21h 58m
American Airlines
Sat 2/213:00 pm
SXM
-
MSN
1 stop8h 14m
American Airlines
Deal found 1/27$850

Find flight deals from Madison to St. Maarten

Keep the following information in mind while searching for Madison to St. Maarten flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$615
(American Airlines)

One-way from

$303
(American Airlines)
Provider with most accurate pricing for Madison Truax Field-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Simpson Bay Princess Juliana flights.
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From Madison Truax Field to St. Maarten
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One-way flight from Madison Truax Field to St. Maarten
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to St. Maarten 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, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Madison to St. Maarten that are best for you.

Fly from

Madison

Fly to

St. Maarten

Route

Depart

Return

Price

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/9

5:44 pm-12:45 pm

1 stop18h 01m

Simpson Bay Princess Juliana

Wed 6/24

1:45 pm-10:13 pm

1 stop9h 28m

$615

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 5/19

4:51 pm-1:21 pm

1 stop19h 30m

Simpson Bay Princess Juliana

Sun 5/24

1:45 pm-10:13 pm

1 stop9h 28m

$655

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/25

5:00 am-4:49 pm

1 stop10h 49m

Simpson Bay Princess Juliana

Wed 4/29

1:35 pm-11:38 am

2 stops23h 03m

$755

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 3/21

6:30 am-12:50 pm

2 stops29h 20m

Simpson Bay Princess Juliana

Mon 3/30

3:50 pm-11:38 am

2 stops20h 48m

$755

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 5/19

3:29 pm-11:37 am

2 stops19h 08m

$303

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 5/19

3:33 pm-12:33 pm

3 stops20h 00m

$3,406

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Best time to book a flight from Madison to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to St. Maarten

What is the cheapest month to book a flight from Madison to St. Maarten?

Currently, February is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $577). Flying from Madison to St. Maarten in June is currently the most expensive (average of $754). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Madison to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to St. Maarten?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to St. Maarten. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to St. Maarten?

    A quick flight from Madison to St. Maarten can take about 18h 01m. American Airlines provides one of the quickest options available for as low as $615. The distance between Madison and St. Maarten is about 2311 mi.

  • Can I find deals for flights from Madison to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Madison to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to St. Maarten.

  • Can I find deals for business class flights from Madison to St. Maarten?

    Yes. Cheapflights offers flight deals from Madison to St. Maarten by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to St. Maarten?

    Currently, February is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $577). Flying from Madison to St. Maarten in June is currently the most expensive (average of $754). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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