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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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Jun 27 — Jul 41
Sat 6/27
Sat 7/4
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 May 28, 2026.

This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/285:52 am
MSN
-
SXM
1 stop7h 01m
Delta
Wed 7/83:20 pm
SXM
-
MSN
1 stop8h 18m
Delta
Deal found 5/25$625
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/301:31 pm
MSN
-
SXM
2 stops23h 22m
Delta
Wed 7/83:20 pm
SXM
-
MSN
1 stop8h 18m
Delta
Deal found 5/25$630
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:52 am
MSN
-
SXM
1 stop7h 01m
Delta
Wed 7/83:20 pm
SXM
-
MSN
1 stop8h 18m
Delta
Deal found 5/25$645
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:45 pm
MSN
-
SXM
2 stops19h 08m
Delta
Thu 7/93:20 pm
SXM
-
MSN
2 stops22h 22m
Delta
Deal found 5/25$650
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Mon 6/295:22 pm
MSN
-
SXM
1 stop19h 28m
American Airlines
Mon 7/61:34 pm
SXM
-
MSN
2 stops19h 17m
American Airlines
Deal found 5/25$660
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:48 am
MSN
-
SXM
1 stop7h 05m
Delta
Wed 7/83:20 pm
SXM
-
MSN
1 stop8h 18m
Delta
Deal found 5/25$729
This Delta deal was found by Cheapflights users on 5/26. 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.
Tue 6/95:52 am
MSN
-
SXM
1 stop7h 01m
Delta
Wed 6/243:18 pm
SXM
-
MSN
1 stop8h 25m
Delta
Deal found 5/26$730
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/285:52 am
MSN
-
SXM
1 stop7h 01m
Delta
Mon 7/63:18 pm
SXM
-
MSN
2 stops22h 24m
Delta
Deal found 5/25$734
This American Airlines deal was found by Cheapflights users on 5/26. 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.
Tue 6/96:42 pm
MSN
-
SXM
2 stops20h 00m
American Airlines
Wed 6/242:22 pm
SXM
-
MSN
2 stops18h 23m
American Airlines
Deal found 5/26$735
This American Airlines deal was found by Cheapflights users on 5/25. 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 6/285:52 pm
MSN
-
SXM
1 stop17h 48m
American Airlines
Tue 7/72:51 pm
SXM
-
MSN
1 stop9h 51m
American Airlines
Deal found 5/25$745
This American Airlines deal was found by Cheapflights users on 5/25. 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 6/275:52 pm
MSN
-
SXM
2 stops20h 50m
American Airlines
Tue 7/72:51 pm
SXM
-
MSN
1 stop9h 51m
American Airlines
Deal found 5/25$750

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 May 28, 2026.

Round-trip from

$625
(Delta)
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 May 28, 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

Cheapest round-trip

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 7/2

5:45 pm-1:53 pm

2 stops19h 08m

Simpson Bay Princess Juliana

Wed 7/8

3:20 pm-10:38 pm

1 stop8h 18m

$650

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/9

5:52 pm-12:40 pm

1 stop17h 48m

Simpson Bay Princess Juliana

Wed 6/24

2:53 pm-12:09 am

1 stop10h 16m

$730
Quickest round-trip

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 6/9

5:52 am-1:53 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Wed 6/24

3:18 pm-10:43 pm

1 stop8h 25m

$730

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 7/2

5:48 am-1:53 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Thu 7/9

3:20 pm-12:42 pm

2 stops22h 22m

$734

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 6/28

5:52 am-1:53 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Mon 7/6

3:18 pm-12:42 pm

2 stops22h 24m

$734

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

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
No data available for this route at this time. Please check back soon.

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 17h 48m. Delta provides one of the quickest options available for as low as $730. 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.

See more FAQs

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