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St. Maarten

$62+ Cheap flights from Wisconsin to St. Maarten

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
1 adult, Economy
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Cheap flight deals from Wisconsin to St. Maarten

Cheapest flights from Wisconsin to St. Maarten
Explore the most affordable flight options available from Wisconsin to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.

This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 3/112:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1$210
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Fri 2/273:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1$215
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/285:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Sat 3/73:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/31$216
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Mon 3/92:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2$222
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Mon 3/92:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/31$230
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/183:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1$233
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/165:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Fri 2/203:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/31$241
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Sat 2/283:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1$250
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Wed 3/112:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1$251
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/253:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/31$258
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/166:42 am
MSP
-
SXM
1 stop29h 33m
Multiple Airlines
Wed 2/253:20 pm
SXM
-
MSP
2 stops30h 07m
Multiple Airlines
Deal found 1/31$373
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/154:36 pm
MSP
-
SXM
1 stop19h 39m
Multiple Airlines
Wed 2/253:20 pm
SXM
-
MSP
2 stops30h 07m
Multiple Airlines
Deal found 1/31$379

Find flight deals from Wisconsin to St. Maarten

Keep the following information in mind while searching for Wisconsin 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

$210
(Travelocity)

One-way from

$62
(Orbitz)

Popular in

June

Cheapest in

August

Average price

$857
Provider with most accurate pricing for Milwaukee-Mitchell-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Simpson Bay Princess Juliana flights.
Search Deals
From Wisconsin to St. Maarten
Search Deals
One-way flight from Wisconsin to St. Maarten
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($286 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($101 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 Wisconsin to St. Maarten that are best for you.

Fly from

Wisconsin

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/23

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Fri 2/27

3:20 pm-11:47 pm

1 stop10h 27m

$215

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/4

10:19 am-2:15 pm

2 stops25h 56m

Simpson Bay Princess Juliana

Wed 3/11

2:20 pm-11:47 pm

1 stop10h 27m

$282

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/20

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Tue 2/24

3:20 pm-11:47 pm

1 stop10h 27m

$304

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/21

7:15 am-4:00 pm

2 stops54h 45m

Simpson Bay Princess Juliana

Sat 2/28

3:20 pm-11:47 pm

1 stop10h 27m

$318

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/11

5:15 am-1:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 3/16

2:20 pm-11:17 pm

1 stop9h 57m

$320

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/4

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sun 3/8

2:20 pm-10:56 am

2 stops21h 36m

$330

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/22

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sun 3/1

3:20 pm-11:22 am

1 stop22h 02m

$342

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 5/20

5:15 am-1:16 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Wed 5/27

2:11 pm-11:41 pm

1 stop10h 30m

$345

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 4/15

1:35 pm-1:16 pm

2 stops22h 41m

Simpson Bay Princess Juliana

Mon 4/20

2:11 pm-11:27 am

1 stop22h 16m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 5/3

1:27 pm-1:16 pm

1 stop22h 49m

Simpson Bay Princess Juliana

Thu 5/7

12:25 pm-11:59 pm

2 stops12h 34m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 48 results
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Best time to book a flight from Wisconsin to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Wisconsin 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 Wisconsin to St. Maarten

What is the cheapest month to book a flight from Wisconsin to St. Maarten?

Currently, February is the cheapest month in which you can book a flight from Wisconsin to St. Maarten (average of $577). Flying from Wisconsin 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 Wisconsin to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Wisconsin to St. Maarten?

    For as low as $553, Spirit Airlines can have you in St. Maarten from Wisconsin in 5h 31m. Airlines will cover a distance of 2536 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Wisconsin to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Wisconsin to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to St. Maarten.

  • Can I find deals for business class flights from Wisconsin to St. Maarten?

    Yes. Cheapflights offers flight deals from Wisconsin 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 Wisconsin to St. Maarten?

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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Wisconsin to St. Maarten

Discover the top 2 airlines that operate flights from Wisconsin 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 2,558,603 searches. Data last updated February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$605Average$832FlexibilityNo cancel feeOn-time71%
DeltaCheapest$609Average$747FlexibilityNo cancel feeOn-timeN/A

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