HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
St. Maarten

$216+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to St. Maarten with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 26, 2026.

This American Airlines deal was found by Cheapflights users on 2/25. 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 4/115:37 pm
MSN
-
SXM
2 stops18h 43m
American Airlines
Sat 4/182:21 pm
SXM
-
MSN
2 stops19h 24m
American Airlines
Deal found 2/25$503
This American Airlines deal was found by Cheapflights users on 2/23. 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 6/65:52 pm
MSN
-
SXM
1 stop17h 51m
American Airlines
Fri 6/121:45 pm
SXM
-
MSN
1 stop8h 50m
American Airlines
Deal found 2/23$605
This United Airlines deal was found by Cheapflights users on 2/23. 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 4/258:30 am
MSN
-
SXM
1 stop7h 19m
United Airlines
Wed 4/293:50 pm
SXM
-
MSN
2 stops24h 10m
United Airlines
Deal found 2/23$613
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Wed 4/811:35 am
MSN
-
SXM
1 stop24h 46m
American Airlines
Wed 4/152:24 pm
SXM
-
MSN
1 stop10h 31m
American Airlines
Deal found 2/22$636
This American Airlines deal was found by Cheapflights users on 2/25. 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.
Sun 6/145:52 pm
MSN
-
SXM
1 stop17h 51m
American Airlines
Sat 6/201:45 pm
SXM
-
MSN
1 stop9h 43m
American Airlines
Deal found 2/25$670
This American Airlines deal was found by Cheapflights users on 2/25. 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 3/288:22 pm
MSN
-
SXM
2 stops18h 06m
American Airlines
Fri 4/34:28 pm
SXM
-
MSN
2 stops19h 11m
American Airlines
Deal found 2/25$834

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 February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$503
(American Airlines)

One-way from

$216
(Kiwi.com)
Provider with most accurate pricing for Madison Truax Field-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Simpson Bay Princess Juliana flights.
Search Deals
From Madison Truax Field to St. Maarten
Search Deals
One-way flight from Madison Truax Field to St. Maarten
Search Deals

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 February 26, 2026.
Use the filters below to find and compare flights from Madison to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/11

8:24 pm-1:21 pm

2 stops15h 57m

Simpson Bay Princess Juliana

Sat 4/18

2:21 pm-8:45 am

2 stops19h 24m

$503

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 4/8

6:00 am-2:43 pm

1 stop7h 43m

Simpson Bay Princess Juliana

Wed 4/15

3:50 pm-8:56 am

2 stops18h 06m

$610

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/25

8:30 am-4:49 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Wed 4/29

3:50 pm-3:00 pm

2 stops24h 10m

$613

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 4/8

3:29 pm-11:37 am

2 stops19h 08m

Simpson Bay Princess Juliana

Wed 4/15

4:35 pm-11:14 am

2 stops19h 39m

$630

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 6/14

5:52 pm-12:43 pm

1 stop17h 51m

Simpson Bay Princess Juliana

Sat 6/20

1:45 pm-10:28 pm

1 stop9h 43m

$670

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 3/8

6:04 pm-11:29 am

2 stops16h 25m

$363

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 3/9

6:28 pm-11:29 am

2 stops16h 01m

$363

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 3/3

5:38 am-2:50 pm

1 stop7h 12m

$373

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 3/5

9:43 am-2:50 pm

2 stops27h 07m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Sorted by cheapest first

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 $573). 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 7h 19m. American Airlines provides one of the quickest options available for as low as $613. The distance between Madison and St. Maarten is about 2311 mi. This flight may include one or multiple stops.

  • 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 $573). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights