When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 52 days in advance, which can save you up to 283% on flights from Wisconsin to St. Maarten compared to booking the week you need them. Waiting 52 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $1,221. For sooner than that we have options available in the next 3 days from $1,483.
Flights from Wisconsin to St. Maarten lean towards being more expensive in July. Prices are generally better when you fly from Wisconsin to St. Maarten in September, with the cheapest ticket starting at $638.
When flying from Wisconsin to St. Maarten, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$539 - $684
Route
Depart
Return
Price
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Tue 7/23
2 stops17h 35m
Simpson Bay Princess Juliana
Tue 7/30
2 stops21h 02m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Tue 7/23
2 stops17h 30m
Simpson Bay Princess Juliana
Mon 7/29
1 stop8h 59m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Tue 7/23
2 stops19h 53m
Simpson Bay Princess Juliana
Mon 7/29
2 stops23h 01m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Thu 7/4
2 stops23h 06m
Simpson Bay Princess Juliana
Mon 7/15
1 stop8h 59m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Sun 9/15
2 stops28h 22m
Simpson Bay Princess Juliana
Wed 9/18
2 stops21h 03m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Wed 5/8
1 stop17h 46m
Simpson Bay Princess Juliana
Wed 5/15
1 stop9h 11m
Milwaukee-MitchellSimpson Bay Princess Juliana
MKE - SXM
MKESXM
Milwaukee-Mitchell
Sat 6/8
1 stop7h 04m
Simpson Bay Princess Juliana
Sat 6/15
1 stop9h 50m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Sun 9/15
1 stop6h 54m
Simpson Bay Princess Juliana
Wed 9/18
1 stop8h 14m
Madison Truax FieldSimpson Bay Princess Juliana
MSN - SXM
MSNSXM
Madison Truax Field
Sun 9/15
1 stop6h 54m
Simpson Bay Princess Juliana
Wed 9/18
2 stops18h 26m
No data available for this route at this time. Please check back soon.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
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