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Saint Martin Island

$544+ Cheap flights from Madison (MSN) to Saint Martin Island

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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
1 adult, Economy
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Cheap flight deals from Madison to Saint Martin Island

Keep the following information in mind while searching for Madison to Saint Martin Island flight deals. Data was last updated January 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$544
(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 Saint Martin Island
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Find flight deals from Madison to Saint Martin Island

Cheapest flights from Madison to Saint Martin Island
Explore the most affordable flight options available from Madison to Saint Martin Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 7, 2026.

This American Airlines deal was found by Cheapflights users on 1/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:23 pmMSN - SXM
2 stops18h 56mAmerican Airlines
Sat 2/285:28 pmSXM - MSN
2 stops18h 35mAmerican Airlines
Deal found 1/7$544
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/73:09 pmMSN - SXM
2 stops19h 49mAmerican Airlines
Sat 2/215:28 pmSXM - MSN
2 stops17h 49mAmerican Airlines
Deal found 1/6$607
This American Airlines deal was found by Cheapflights users on 1/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/113:09 pmMSN - SXM
2 stops19h 20mAmerican Airlines
Wed 2/255:28 pmSXM - MSN
2 stops17h 43mAmerican Airlines
Deal found 1/7$664
This United Airlines deal was found by Cheapflights users on 1/6. 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.
Sat 4/258:30 amMSN - SXM
1 stop7h 19mUnited Airlines
Wed 4/291:35 pmSXM - MSN
2 stops23h 03mUnited Airlines
Deal found 1/6$735
This Delta deal was found by Cheapflights users on 1/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:38 amMSN - SXM
1 stop8h 25mDelta
Sat 2/213:40 pmSXM - MSN
1 stop9h 08mDelta
Deal found 1/7$792

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Saint Martin Island 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 7, 2026.
Use the filters below to find and compare flights from Madison to Saint Martin Island that are best for you.

Fly from

Madison

Fly to

Saint Martin Island

Route

Depart

Return

Price

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 2/21

10:54 am-2:16 pm

1 stop25h 22m

Simpson Bay Princess Juliana

Sat 2/28

5:28 pm-10:03 am

2 stops18h 35m

$553

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 2/7

8:10 am-1:42 pm

1 stop27h 32m

Simpson Bay Princess Juliana

Sat 2/21

5:28 pm-9:17 am

2 stops17h 49m

$616

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 2/11

3:09 pm-12:29 pm

2 stops19h 20m

Simpson Bay Princess Juliana

Wed 2/25

5:28 pm-9:11 am

2 stops17h 43m

$664

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 4/25

6:30 am-4:49 pm

1 stop9h 19m

Simpson Bay Princess Juliana

Wed 4/29

3:50 pm-7:19 pm

2 stops28h 29m

$735

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 2/7

5:38 am-4:03 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Sat 2/21

3:40 pm-10:48 pm

1 stop9h 08m

$792

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Best time to book a flight from Madison to Saint Martin Island

Have a flexible travel schedule? Discover the best time to fly to Saint Martin Island 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 Saint Martin Island

What is the cheapest month to book a flight from Madison to Saint Martin Island?

Currently, March is the cheapest month in which you can book a flight from Madison to Saint Martin Island (average of $584). Flying from Madison to Saint Martin Island 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 Saint Martin Island

Get insights into the airlines that provide service to Saint Martin Island. 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 Saint Martin Island. Reviews last updated January 7, 2026.
Read through reviews of airlines operating flights from Madison to Saint Martin Island, such as Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,025 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

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
8,025 reviews
Delta
7.9
Good
8,025 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

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 Saint Martin Island. 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 Saint Martin Island?

    Madison Truax Field (MSN), located 5.4 mi from the city center, is the airport you fly out of when you book flights from Madison to Saint Martin Island.

  • How long is the flight from Madison to Saint Martin Island?

    Departing from Madison to Saint Martin Island will take you 25h 22m. There are 2311 mi between Madison and Saint Martin Island.

  • Can I find deals for flights from Madison to Saint Martin Island that include hotel bookings?

    Yes. In addition to deals on Madison to Saint Martin Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Saint Martin Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Saint Martin Island.

  • Can I find deals for business class flights from Madison to Saint Martin Island?

    Yes. Cheapflights offers flight deals from Madison to Saint Martin Island 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 Saint Martin Island?

    Currently, March is the cheapest month in which you can book a flight from Madison to Saint Martin Island (average of $584). Flying from Madison to Saint Martin Island 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 Saint Martin Island

Discover the top airline that operate flights from Madison to Saint Martin Island. 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 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$587Average$645FlexibilityNo cancel feeOn-timeN/A

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