HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
St. Maarten

$615+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SXM
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to St. Maarten with Cheapflights

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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

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 February 2, 2026.

This Delta deal was found by Cheapflights users on 1/31. 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 9/285:45 am
MSN
-
SXM
1 stop7h 05m
Delta
Wed 10/73:14 pm
SXM
-
MSN
1 stop8h 20m
Delta
Deal found 1/31$615
This Delta deal was found by Cheapflights users on 1/31. 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 9/295:50 pm
MSN
-
SXM
2 stops19h 00m
Delta
Wed 10/73:14 pm
SXM
-
MSN
2 stops22h 42m
Delta
Deal found 1/31$620
This Delta deal was found by Cheapflights users on 1/31. 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 9/285:45 am
MSN
-
SXM
1 stop7h 05m
Delta
Fri 10/93:14 pm
SXM
-
MSN
1 stop8h 20m
Delta
Deal found 1/31$624
This Delta deal was found by Cheapflights users on 1/31. 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 9/299:26 am
MSN
-
SXM
2 stops27h 24m
Delta
Fri 10/93:14 pm
SXM
-
MSN
1 stop8h 20m
Delta
Deal found 1/31$629
This Delta deal was found by Cheapflights users on 1/31. 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 10/45:45 am
MSN
-
SXM
1 stop7h 05m
Delta
Wed 10/73:14 pm
SXM
-
MSN
1 stop8h 20m
Delta
Deal found 1/31$633
This Delta deal was found by Cheapflights users on 1/31. 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 9/285:45 am
MSN
-
SXM
1 stop7h 05m
Delta
Mon 10/53:20 pm
SXM
-
MSN
1 stop8h 15m
Delta
Deal found 1/31$640
This Delta deal was found by Cheapflights users on 1/31. 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 9/299:26 am
MSN
-
SXM
2 stops27h 24m
Delta
Mon 10/53:20 pm
SXM
-
MSN
2 stops18h 30m
Delta
Deal found 1/31$645
This Delta deal was found by Cheapflights users on 1/31. 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 9/285:45 am
MSN
-
SXM
1 stop7h 05m
Delta
Sun 10/43:20 pm
SXM
-
MSN
1 stop8h 15m
Delta
Deal found 1/31$649
This American Airlines deal was found by Cheapflights users on 2/1. 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 5/95:08 pm
MSN
-
SXM
1 stop19h 13m
American Airlines
Sat 5/162:16 pm
SXM
-
MSN
1 stop10h 40m
American Airlines
Deal found 2/1$650
This Delta deal was found by Cheapflights users on 1/31. 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 9/291:45 pm
MSN
-
SXM
2 stops23h 05m
Delta
Sun 10/43:20 pm
SXM
-
MSN
1 stop8h 15m
Delta
Deal found 1/31$654
This American Airlines deal was found by Cheapflights users on 1/31. 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 4/2011:35 am
MSN
-
SXM
1 stop24h 46m
American Airlines
Mon 4/274:35 pm
SXM
-
MSN
2 stops19h 29m
American Airlines
Deal found 1/31$655

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 February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$645
(American Airlines)
Provider with most accurate pricing for Madison Truax Field-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Simpson Bay Princess Juliana flights.
Search Deals
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 February 2, 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 5/9

5:08 pm-11:38 am

2 stops17h 30m

Simpson Bay Princess Juliana

Sat 5/16

4:35 pm-11:14 am

2 stops19h 39m

$645

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 4/20

4:12 pm-1:16 pm

2 stops20h 04m

Simpson Bay Princess Juliana

Mon 4/27

2:21 pm-11:04 am

2 stops21h 43m

$645

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 6/15

5:44 pm-12:45 pm

1 stop18h 01m

Simpson Bay Princess Juliana

Sat 6/20

1:45 pm-10:13 pm

1 stop9h 28m

$688

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Mon 6/15

3:53 pm-12:33 pm

2 stops19h 40m

Simpson Bay Princess Juliana

Sat 6/20

3:50 pm-8:53 am

2 stops18h 03m

$753

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-3:00 pm

2 stops24h 10m

$755

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

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, February is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $577). 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.

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 30m. American Airlines provides one of the quickest options available for as low as $645. 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, February is the cheapest month in which you can book a flight from Madison to St. Maarten (average of $577). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
Minneapolis to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Montego Bay flights
Minneapolis to Saint Thomas Island flights
Minneapolis to Punta Cana flights
Milwaukee to Luis Munoz Marin Intl flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
Minneapolis to Montego Bay flights
O'Hare Intl to Simpson Bay flights
Minneapolis to Nassau flights
Milwaukee to Punta Cana flights
Minneapolis to Oranjestad flights
Minneapolis to Providenciales flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
Madison to Luis Munoz Marin Intl flights
O'Hare Intl to Christiansted flights
Appleton to Luis Munoz Marin Intl flights
O'Hare Intl to Castries flights
Minneapolis to George Town flights
Green Bay to Luis Munoz Marin Intl flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Puerto Plata flights
Minneapolis to Simpson Bay flights
O'Hare Intl to St. John's flights
Minneapolis to Willemstad flights
Madison to Punta Cana flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Ponce flights
Milwaukee to Saint Thomas Island flights
O'Hare Intl to Kingston flights
O'Hare Intl to Road Town flights
O'Hare Intl to Santiago de los Caballeros flights
Milwaukee to Montego Bay flights
Madison to Oranjestad flights
Minneapolis to Road Town flights
Minneapolis to Santo Domingo flights
Milwaukee to Nassau flights
O'Hare Intl to Georgetown flights
Milwaukee to Simpson Bay flights
Minneapolis to Puerto Plata flights
Minneapolis to Christiansted flights
Minneapolis to Castries flights
Milwaukee to Oranjestad flights
Milwaukee to Puerto Plata flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
Cookie settings©2026 Cheapflights