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St. Maarten

$625+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
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 January 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$618
(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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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 January 12, 2026.

This American Airlines deal was found by Cheapflights users on 1/11. 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.
Sat 5/26:02 pm
MSN
-
SXM
2 stops16h 35m
American Airlines
Sat 5/92:56 pm
SXM
-
MSN
1 stop9h 32m
American Airlines
Deal found 1/11$625
This American Airlines deal was found by Cheapflights users on 1/11. 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.
Sun 3/228:24 pm
MSN
-
SXM
2 stops18h 04m
American Airlines
Sun 3/294:01 pm
SXM
-
MSN
1 stop25h 46m
American Airlines
Deal found 1/11$641
This American Airlines deal was found by Cheapflights users on 1/11. 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.
Sun 5/38:25 pm
MSN
-
SXM
2 stops17h 55m
American Airlines
Sat 5/92:56 pm
SXM
-
MSN
1 stop9h 32m
American Airlines
Deal found 1/11$643
This American Airlines deal was found by Cheapflights users on 1/12. 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 3/14:16 pm
MSN
-
SXM
2 stops20h 03m
American Airlines
Thu 3/55:28 pm
SXM
-
MSN
2 stops19h 08m
American Airlines
Deal found 1/12$648
This American Airlines deal was found by Cheapflights users on 1/11. 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.
Sat 2/73:00 pm
MSN
-
SXM
2 stops19h 58m
American Airlines
Sat 2/215:01 pm
SXM
-
MSN
2 stops18h 16m
American Airlines
Deal found 1/11$676

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 12, 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

Sat 5/2

6:02 pm-11:37 am

2 stops16h 35m

Simpson Bay Princess Juliana

Sat 5/9

2:56 pm-11:28 pm

1 stop9h 32m

$625

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 3/22

8:24 pm-3:28 pm

2 stops18h 04m

Simpson Bay Princess Juliana

Sun 3/29

4:01 pm-4:47 pm

1 stop25h 46m

$641

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 5/3

8:25 pm-3:20 pm

2 stops17h 55m

Simpson Bay Princess Juliana

Sat 5/9

2:56 pm-11:28 pm

1 stop9h 32m

$643

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 3/1

5:23 pm-2:19 pm

2 stops18h 56m

Simpson Bay Princess Juliana

Thu 3/5

3:21 pm-11:40 pm

1 stop10h 19m

$648

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

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 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.

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 January 12, 2026.
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
8,039 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

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
8,039 reviews
Delta
7.9
Good
8,039 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

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 53m. American Airlines provides one of the quickest options available for as low as $618. 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 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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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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$645FlexibilityNo cancel feeOn-timeN/A

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