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Cheap flights from Madison to St. Maarten from $506

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to St. Maarten departing on 2/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to St. Maarten

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:16 pm - 4:27 pm
MSN
-
SXM
18h 11m2 stops
American Airlines Logo
3:05 pm - 10:10 am
SXM
-
MSN
21h 05m2 stops
$506American Airlines
Sun, Feb 22 - Fri, Feb 27
American Airlines Logo
3:57 pm - 12:38 pm
MSN
-
SXM
18h 41m2 stops
American Airlines Logo
1:41 pm - 10:57 pm
SXM
-
MSN
11h 16m2 stops
$536American Airlines
Wed, Feb 11 - Wed, Feb 25
American Airlines Logo
3:09 pm - 12:58 pm
MSN
-
SXM
19h 49m2 stops
American Airlines Logo
5:33 pm - 10:55 am
SXM
-
MSN
19h 22m2 stops
$561American Airlines
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
4:47 pm - 2:31 pm
MSN
-
SXM
19h 44m1 stop
American Airlines Logo
4:24 pm - 11:41 pm
SXM
-
MSN
9h 17m1 stop
$567American Airlines
Thu, Jan 15 - Thu, Jan 22
United Airlines Logo
12:57 pm - 1:50 pm
MSN
-
SXM
22h 53m2 stops
United Airlines Logo
1:52 pm - 10:37 pm
SXM
-
MSN
9h 45m1 stop
$587United Airlines
Wed, Mar 4 - Wed, Mar 11
United Airlines Logo
5:44 pm - 12:50 pm
MSN
-
SXM
18h 06m2 stops
United Airlines Logo
3:55 pm - 3:14 pm
SXM
-
MSN
24h 19m2 stops
$592United Airlines
Tue, Mar 10 - Fri, Mar 20
American Airlines Logo
10:58 am - 1:16 pm
MSN
-
SXM
25h 18m1 stop
American Airlines Logo
4:01 pm - 4:50 pm
SXM
-
MSN
25h 49m1 stop
$608American Airlines
Tue, Mar 10 - Fri, Mar 20
United Airlines Logo
6:00 am - 3:51 pm
MSN
-
SXM
7h 51m1 stop
United Airlines Logo
2:52 pm - 11:44 pm
SXM
-
MSN
10h 52m1 stop
$611United Airlines
Sun, Jan 25 - Wed, Jan 28
American Airlines Logo
5:07 pm - 2:05 pm
MSN
-
SXM
18h 58m2 stops
American Airlines Logo
2:21 pm - 11:40 pm
SXM
-
MSN
10h 19m1 stop
$617American Airlines
Wed, Mar 4 - Wed, Mar 11
United Airlines Logo
6:05 am - 3:51 pm
MSN
-
SXM
7h 46m1 stop
United Airlines Logo
2:52 pm - 10:16 am
SXM
-
MSN
21h 24m2 stops
$618United Airlines
Sun, Feb 22 - Fri, Feb 27

United Airlines flights from Madison to St. Maarten

Our best United Airlines deals on Madison to St. Maarten flight tickets
United Airlines
Mar 4
MSN12:57 pmMadison Truax Field
22h 53m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Mar 11
SXM1:52 pmSimpson Bay Princess Juliana
9h 45m
1 stop
MSN10:37 pmMadison Truax Field
$587
Find similar
United Airlines
Mar 4
MSN12:57 pmMadison Truax Field
22h 53m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Mar 11
SXM3:55 pmSimpson Bay Princess Juliana
23h 07m
2 stops
MSN2:02 pmMadison Truax Field
$607
Find similar
United Airlines
Jan 25
MSN6:00 amMadison Truax Field
7h 51m
1 stop
SXM3:51 pmSimpson Bay Princess Juliana
Jan 28
SXM2:52 pmSimpson Bay Princess Juliana
10h 52m
1 stop
MSN11:44 pmMadison Truax Field
$611
Find similar

American Airlines flights from Madison to St. Maarten

Our best American Airlines deals on Madison to St. Maarten flight tickets
American Airlines
Feb 11
MSN4:30 pmMadison Truax Field
18h 08m
2 stops
SXM12:38 pmSimpson Bay Princess Juliana
Feb 25
SXM3:20 pmSimpson Bay Princess Juliana
19h 53m
2 stops
MSN9:13 amMadison Truax Field
$536
Find similar
American Airlines
Jan 15
MSN3:09 pmMadison Truax Field
19h 49m
2 stops
SXM12:58 pmSimpson Bay Princess Juliana
Jan 22
SXM5:33 pmSimpson Bay Princess Juliana
19h 22m
2 stops
MSN10:55 amMadison Truax Field
$561
Find similar
American Airlines
Jan 23
MSN5:51 pmMadison Truax Field
17h 07m
2 stops
SXM12:58 pmSimpson Bay Princess Juliana
Jan 31
SXM3:23 pmSimpson Bay Princess Juliana
10h 17m
1 stop
MSN11:40 pmMadison Truax Field
$566
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated December 11, 2025.
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

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 2/22

8:16 pm-4:27 pm

2 stops18h 11m

Simpson Bay Princess Juliana

Fri 2/27

3:05 pm-10:10 am

2 stops21h 05m

$506

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 2/11

3:57 pm-12:38 pm

2 stops18h 41m

Simpson Bay Princess Juliana

Wed 2/25

1:41 pm-10:57 pm

2 stops11h 16m

$536

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 1/15

3:09 pm-12:58 pm

2 stops19h 49m

Simpson Bay Princess Juliana

Thu 1/22

5:33 pm-10:55 am

2 stops19h 22m

$561

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 1/15

4:47 pm-2:31 pm

1 stop19h 44m

Simpson Bay Princess Juliana

Thu 1/22

4:24 pm-11:41 pm

1 stop9h 17m

$567

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 3/4

12:57 pm-1:50 pm

2 stops22h 53m

Simpson Bay Princess Juliana

Wed 3/11

1:52 pm-10:37 pm

1 stop9h 45m

$587

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 3/10

5:44 pm-12:50 pm

2 stops18h 06m

Simpson Bay Princess Juliana

Fri 3/20

3:55 pm-3:14 pm

2 stops24h 19m

$592

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Tue 3/10

10:58 am-1:16 pm

1 stop25h 18m

Simpson Bay Princess Juliana

Fri 3/20

4:01 pm-4:50 pm

1 stop25h 49m

$608

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 1/25

6:00 am-3:51 pm

1 stop7h 51m

Simpson Bay Princess Juliana

Wed 1/28

2:52 pm-11:44 pm

1 stop10h 52m

$611

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Wed 3/4

5:07 pm-2:05 pm

2 stops18h 58m

Simpson Bay Princess Juliana

Wed 3/11

2:21 pm-11:40 pm

1 stop10h 19m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sun 2/22

6:05 am-3:51 pm

1 stop7h 46m

Simpson Bay Princess Juliana

Fri 2/27

2:52 pm-10:16 am

2 stops21h 24m

$618

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to St. Maarten from

How to get the cheapest flight ticket from Madison to St. Maarten

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to St. Maarten?

According to our data, Wednesday is the cheapest day to fly to St. Maarten from Madison. The lowest ticket price found for a Wednesday departure recently was $644. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to St. Maarten is Thursday, with ticket prices averaging around $940.

What is the cheapest time of day to depart on your flight to St. Maarten?

In the afternoon is the cheapest time of day to fly from Madison to St. Maarten when you can find flight prices for as low as $719. Flying to St. Maarten in the afternoon is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to St. Maarten is in the evening when prices are around $1,229.

Can stopping save me money on Madison to St. Maarten flights?

You could potentially save up to 39% on your flight if you consider stops on a Madison to St. Maarten flight.

Cheap Madison to St. Maarten flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to St. Maarten

Fastest flight time

6h 50m

Direct flights

None
The fastest flight from Madison to St. Maarten takes 6h 50m
There are no direct flights from Madison to St. Maarten. There are no popular flight routes from Madison to St. Maarten.
Search flight deals

  • When did momondo last update prices for flights from Madison Truax Field Airport to St. Maarten?

    Prices for flights from Madison Truax Field Airport to St. Maarten were last updated today.

  • How many operators does momondo search for flights from Madison Truax Field Airport to St. Maarten?

  • How old do you have to be to fly from Madison Truax Field Airport to St. Maarten?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Madison Truax Field Airport to St. Maarten.

  • What documentation or ID do you need to fly to St. Maarten?

    The travel and health documents required for your trip to St. Maarten can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at St. Maarten. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Madison to St. Maarten

Compare and see reviews for airlines that fly from Madison to St. Maarten with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $587Free CancellationRating
7.9
8,008 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to St. Maarten?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Madison to St. Maarten for you.

Can I find flights from Madison to St. Maarten with flexible booking policies on momondo?

momondo does allow users to show only those flights to St. Maarten from Madison which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Madison to St. Maarten?

momondo helps you find the best flight between Madison and St. Maarten by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Madison to St. Maarten right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Madison to St. Maarten flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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