$491+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Sep 25 — Oct 21
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Madison to St. Maarten
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Best
Last-minute
Cheapest flights from Madison to St. MaartenExplore 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 26, 2026.
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 26, 2026.
This American Airlines deal was found by Cheapflights users on 8/23. 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 11/177:08 pm -
2 stops19h 23m
Mon 11/233:00 pm -
1 stop10h 59m
Deal found 8/23![American Airlines logo]()
$548
This American Airlines deal was found by Cheapflights users on 8/23. 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 12/66:38 pm -
2 stops19h 53m
Sun 12/133:26 pm -
2 stops18h 43m
Deal found 8/23![American Airlines logo]()
$553
This American Airlines deal was found by Cheapflights users on 8/24. 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 9/1812:56 pm -
2 stops23h 27m
Sun 9/202:23 pm -
2 stops23h 03m
Deal found 8/24![American Airlines logo]()
$773
This Delta deal was found by Cheapflights users on 8/24. 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 9/185:50 am -
1 stop7h 03m
Sun 9/203:18 pm -
1 stop8h 23m
Deal found 8/24![Delta logo]()
$1,430
Best flights from Madison to St. MaartenDiscover carefully curated flight deals from Madison to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
Discover carefully curated flight deals from Madison to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
This American Airlines deal was found by Cheapflights users on 8/26. 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 1/263:28 pm -
2 stops19h 30m
Fri 2/52:50 pm -
1 stop10h 51m
Deal found 8/26![American Airlines logo]()
$491
This American Airlines deal was found by Cheapflights users on 8/21. 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 2/27:05 pm -
2 stops19h 23m
Sun 2/72:50 pm -
2 stops19h 16m
Deal found 8/21![American Airlines logo]()
$560
Last-minute flights from Madison to St. MaartenDiscover last-minute flight deals from Madison to St. Maarten. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to St. Maarten. Data last updated August 26, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/24. 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 9/1812:56 pm -
2 stops23h 27m
Sun 9/202:23 pm -
2 stops23h 03m
Deal found 8/24![American Airlines logo]()
$773
This Delta deal was found by Cheapflights users on 8/24. 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 9/185:50 am -
1 stop7h 03m
Sun 9/203:18 pm -
1 stop8h 23m
Deal found 8/24![Delta logo]()
$1,430
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 August 26, 2026.
Round-trip from | $491 (American Airlines) |
|---|
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 7,457,451 searches. Data last updated August 26, 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
Cheapest round-trip
Quickest round-trip
MadisonSimpson Bay
MSN Madison Truax Field - SXM Simpson Bay Princess Juliana
MSNSXM
Madison Truax Field
Tue 1/26
3:28 pm-12:58 pm
2 stops19h 30m
Simpson Bay Princess Juliana
Fri 2/5
2:50 pm-11:41 pm
1 stop10h 51m
$491
MadisonSimpson Bay
MSN Madison Truax Field - SXM Simpson Bay Princess Juliana
MSNSXM
Madison Truax Field
Tue 2/2
7:05 pm-4:28 pm
2 stops19h 23m
Simpson Bay Princess Juliana
Sun 2/7
2:50 pm-8:06 am
2 stops19h 16m
$560
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.
MSN-SXM
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
MSN-SX0
MSN-SXM
No data available for this route at this time. Please check back soon.
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 26, 2026.
Get a feel of what it's like to fly with 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.
Overall
7.1
Boarding
7.5
Comfort
7.2
Crew
7.9
Food
6.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Overall
7.1
Boarding
7.5
Comfort
7.2
Crew
7.9
Food
6.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
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.
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Madison and St. Maarten flights
Browse other Madison and St. Maarten flight options. Last updated on August 26, 2026.
Popular flight searches
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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 7,457,451 searches. Data last updated August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$582 | Average$774 | FlexibilityNo cancel fee | On-time71% |