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St. Maarten

$113+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$298
(Cheapflightsfares)

One-way from

$113
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$671
Provider with most accurate pricing for Milwaukee-Mitchell-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Simpson Bay Princess Juliana flights.
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From Wisconsin to St. Maarten
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One-way flight from Wisconsin to St. Maarten
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Highest demand for flights based on searches. 24% potential increase in price ($282 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease ($115 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 10/29$314
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/143:20 pmORD - SXM
1 stop20h 55mMultiple Airlines
Wed 12/243:20 pmSXM - ORD
1 stop25h 42mMultiple Airlines
Deal found 10/28$318
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/203:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 10/28$332
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 12/116:15 amORD - SXM
1 stop30h 00mMultiple Airlines
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 10/28$337
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/285:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fri 12/53:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 10/29$349
This Gotogate deal was found by Cheapflights users on 10/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:20 pmORD - SXM
1 stop19h 10mMultiple Airlines
Wed 12/103:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 10/28$351
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:34 pmORD - SXM
2 stops16h 41mSpirit Airlines
Mon 11/173:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/29$355
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:47 pmORD - SXM
2 stops19h 28mSpirit Airlines
Wed 12/103:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 10/28$357
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/164:22 pmORD - SXM
2 stops19h 53mMultiple Airlines
Wed 1/73:20 pmSXM - ORD
1 stop30h 04mMultiple Airlines
Deal found 10/29$359
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/137:07 pmORD - SXM
1 stop17h 13mAmerican Airlines
Sat 12/203:04 pmSXM - ORD
Nonstop5h 54mAmerican Airlines
Deal found 10/28$365
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Thu 12/46:12 amMSP - SXM
1 stop30h 03mMultiple Airlines
Wed 12/103:20 pmSXM - MSP
2 stops42h 16mMultiple Airlines
Deal found 10/30$422
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/149:06 amMSP - SXM
2 stops27h 09mMultiple Airlines
Wed 12/243:20 pmSXM - MSP
1 stop25h 58mMultiple Airlines
Deal found 10/29$430

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 October 30, 2025.
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

Thu 12/11

6:15 am-2:15 pm

1 stop30h 00m

Simpson Bay Princess Juliana

Wed 12/17

3:20 pm-12:09 am

1 stop10h 49m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/14

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sun 12/21

5:00 pm-11:44 pm

1 stop8h 44m

$371

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:43 pm

1 stop8h 50m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/3

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Fri 12/5

3:53 pm-12:01 am

1 stop10h 08m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/10

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:43 pm

1 stop8h 50m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 12/1

5:23 am-2:55 pm

1 stop7h 32m

Simpson Bay Princess Juliana

Fri 12/5

3:53 pm-12:01 am

1 stop10h 08m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/17

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-9:14 pm

1 stop9h 29m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 12/3

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-10:43 pm

1 stop9h 18m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 12/1

5:23 am-2:55 pm

1 stop7h 32m

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-10:43 pm

1 stop9h 18m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/7

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:43 pm

1 stop8h 50m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 59 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, January is the cheapest month in which you can book a flight from Wisconsin to St. Maarten (average of $566). Flying from Wisconsin to St. Maarten in August is currently the most expensive (average of $712). 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.

What is the cheapest time of day to fly from WI to SX?

Find hourly flight availability from Wisconsin to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Wisconsin to St. Maarten is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 25% on airfare.

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 $371, United Airlines can have you in St. Maarten from Wisconsin in 5h 12m. Airlines will cover a distance of 2204 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, January is the cheapest month in which you can book a flight from Wisconsin to St. Maarten (average of $566). Flying from Wisconsin to St. Maarten in August is currently the most expensive (average of $712). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$584Average$696FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$605Average$793FlexibilityNo cancel feeOn-time71%

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