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St. Maarten

$293+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$617
(American Airlines)

One-way from

$293
(American Airlines)

Popular in

February

Cheapest in

July
From Madison Truax Field to St. Maarten
Search Deals
One-way flight from Madison Truax Field to St. Maarten
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Highest demand for flights based on searches. 28% potential increase in price ($307 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($71 potential savings vs. average RT price).
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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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. 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 12/114:20 pmMSN - SXM
2 stops21h 20mAmerican Airlines
Tue 12/163:35 pmSXM - MSN
1 stop10h 06mAmerican Airlines
Deal found 8/13$617
This American Airlines deal was found by Cheapflights users on 8/13. 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 12/114:20 pmMSN - SXM
2 stops21h 20mAmerican Airlines
Mon 12/154:45 pmSXM - MSN
2 stops19h 58mAmerican Airlines
Deal found 8/13$642
This Delta deal was found by Cheapflights users on 8/14. 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.
Wed 10/155:30 amMSN - SXM
1 stop7h 19mDelta
Wed 10/223:14 pmSXM - MSN
1 stop8h 31mDelta
Deal found 8/14$772
This American Airlines deal was found by Cheapflights users on 8/13. 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 12/265:11 pmMSN - SXM
2 stops16h 59mAmerican Airlines
Sun 1/42:15 pmSXM - MSN
1 stop26h 53mAmerican Airlines
Deal found 8/13$1,418

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 August 14, 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

Thu 12/11

4:20 pm-3:40 pm

2 stops21h 20m

Simpson Bay Princess Juliana

Tue 12/16

4:45 pm-10:20 am

2 stops19h 35m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 10/15

8:25 pm-3:15 pm

2 stops17h 50m

Simpson Bay Princess Juliana

Wed 10/22

2:40 pm-11:25 am

2 stops21h 45m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 12/11

4:20 pm-3:40 pm

2 stops21h 20m

Simpson Bay Princess Juliana

Mon 12/15

4:45 pm-10:43 am

2 stops19h 58m

$642

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 10/15

5:30 am-1:49 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Wed 10/22

3:14 pm-10:45 pm

1 stop8h 31m

$772

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Fri 12/26

5:11 pm-12:10 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Sun 1/4

2:15 pm-3:08 pm

1 stop26h 53m

$1,418

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 1/10

3:30 pm-2:05 pm

2 stops20h 35m

$293

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 1/10

7:00 am-1:44 pm

3 stops28h 44m

$2,615

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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, September is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $459). Flying from Madison to St. Maarten in March is currently the most expensive (average of $654). 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 August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to St. Maarten as you normally would.

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 August 14, 2025.
Get a feel of what it's like to fly with Delta and American Airlines 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
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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, September is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $459). Flying from Madison to St. Maarten in March is currently the most expensive (average of $654). 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 2 airlines flying from Madison to St. Maarten

Discover the top 2 airlines 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$645FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$647Average$784FlexibilityNo cancel feeOn-time71%

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