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St. Maarten

$536+ Cheap flights from Madison (MSN) to St. Maarten

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/10. 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.
Fri 12/128:08 pmMSN - SXM
1 stop17h 00mAmerican Airlines
Wed 12/172:51 pmSXM - MSN
1 stop10h 49mAmerican Airlines
Deal found 12/10$966
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Thu 12/113:55 pmMSN - SXM
2 stops20h 25mAmerican Airlines
Tue 12/165:25 pmSXM - MSN
2 stops19h 06mAmerican Airlines
Deal found 12/11$1,021
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:38 amMSN - SXM
1 stop6h 50mDelta
Tue 12/163:53 pmSXM - MSN
1 stop8h 33mDelta
Deal found 12/10$1,123
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/115:23 pmMSN - SXM
2 stops42h 27mUnited Airlines
Tue 12/162:52 pmSXM - MSN
1 stop9h 53mUnited Airlines
Deal found 12/10$1,335

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 December 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$536
(American Airlines)

Popular in

February

Cheapest in

July

Average price

$726
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
Search Deals
Highest demand for flights based on searches. 31% potential increase in price ($375 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($66 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 12, 2025.
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

Wed 2/11

3:57 pm-12:38 pm

2 stops18h 41m

Simpson Bay Princess Juliana

Wed 2/25

1:41 pm-10:57 pm

2 stops11h 16m

$536

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 1/15

3:09 pm-12:58 pm

2 stops19h 49m

Simpson Bay Princess Juliana

Thu 1/22

5:33 pm-10:55 am

2 stops19h 22m

$561

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 1/23

5:51 pm-12:58 pm

2 stops17h 07m

Simpson Bay Princess Juliana

Sat 1/31

3:23 pm-11:40 pm

1 stop10h 17m

$566

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 3/4

12:57 pm-1:50 pm

2 stops22h 53m

Simpson Bay Princess Juliana

Wed 3/11

1:52 pm-10:37 pm

1 stop9h 45m

$587

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 2/7

4:30 pm-1:42 pm

1 stop19h 12m

Simpson Bay Princess Juliana

Sat 2/21

5:28 pm-10:10 am

2 stops18h 42m

$610

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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, March is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $584). Flying from Madison to St. Maarten in November is currently the most expensive (average of $649). 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.

What is the cheapest time of day to fly from MSN to SX?

Find hourly flight availability from Madison to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

When flying from Madison to St. Maarten, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 45% versus a flight in the evening.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St. Maarten. Reviews last updated December 12, 2025.
Get a feel of what it's like to fly with Delta from Madison to St. Maarten by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Crew

8.5

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 08m. American Airlines provides one of the quickest options available for as low as $536. 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, March is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $584). Flying from Madison to St. Maarten in November is currently the most expensive (average of $649). 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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Top airline flying from Madison to St. Maarten

Discover the top airline that operate flights from Madison to St. Maarten. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$652FlexibilityNo cancel feeOn-timeN/A

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