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St. Maarten

$318+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
1 adult, Economy
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Cheap 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 November 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$612
(Delta)

One-way from

$318
(Delta)

Popular in

February

Cheapest in

January

Average price

$700
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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Highest demand for flights based on searches. 16% potential increase in price ($146 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 10, 2025.

This Delta deal was found by Cheapflights users on 11/9. 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.
Fri 12/125:38 amMSN - SXM
1 stop6h 50mDelta
Wed 12/173:53 pmSXM - MSN
1 stop8h 33mDelta
Deal found 11/9$612
This American Airlines deal was found by Cheapflights users on 11/10. 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 12/125:00 amMSN - SXM
2 stops9h 25mAmerican Airlines
Wed 12/173:20 pmSXM - MSN
2 stops21h 17mAmerican Airlines
Deal found 11/10$617
This American Airlines deal was found by Cheapflights users on 11/10. 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.
Thu 12/113:55 pmMSN - SXM
1 stop19h 57mAmerican Airlines
Tue 12/163:20 pmSXM - MSN
2 stops20h 35mAmerican Airlines
Deal found 11/10$628
This Delta deal was found by Cheapflights users on 11/10. 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 11/10$702
This American Airlines deal was found by Cheapflights users on 11/8. 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 12/199:30 pmMSN - SXM
2 stops17h 03mAmerican Airlines
Fri 12/262:59 pmSXM - MSN
1 stop11h 00mAmerican Airlines
Deal found 11/8$800
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Tue 12/236:00 amMSN - SXM
1 stop7h 51mUnited Airlines
Tue 12/302:52 pmSXM - MSN
1 stop10h 05mUnited Airlines
Deal found 11/7$1,984
This WestJet deal was found by Cheapflights users on 11/7. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:03 pmMSN - SXM
2 stops44h 18mWestJet
Tue 12/304:20 pmSXM - MSN
2 stops18h 45mWestJet
Deal found 11/7$3,588

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 November 10, 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

Fri 12/12

5:38 am-2:28 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Wed 12/17

3:53 pm-10:26 pm

1 stop8h 33m

$612

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 12/12

1:40 pm-12:10 pm

2 stops20h 30m

Simpson Bay Princess Juliana

Wed 12/17

5:25 pm-10:37 am

2 stops19h 12m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 2/11

1:16 pm-12:40 pm

2 stops21h 24m

Simpson Bay Princess Juliana

Wed 2/25

4:40 pm-10:59 pm

1 stop8h 19m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

3:12 pm-2:20 pm

2 stops21h 08m

Simpson Bay Princess Juliana

Tue 12/16

3:20 pm-9:55 am

2 stops20h 35m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 2/7

3:09 pm-2:31 pm

2 stops21h 22m

Simpson Bay Princess Juliana

Sat 2/14

3:19 pm-9:10 am

2 stops19h 51m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

5:00 am-4:25 pm

2 stops9h 25m

$318

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

5:38 am-2:28 pm

1 stop6h 50m

$318

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 12/12

5:00 am-4:25 pm

2 stops9h 25m

$318

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 12/12

5:38 am-2:28 pm

1 stop6h 50m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

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, January is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $565). 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 November 10, 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 November 10, 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

Food

7.3

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

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

Food

7.3

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

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 6h 50m. Delta provides one of the quickest options available for as low as $612. 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, January is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $565). 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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Alternative routes for Madison to St. Maarten

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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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$645FlexibilityNo cancel feeOn-timeN/A

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