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St. Maarten

$70+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Jan 19 — Jan 261
Mon 1/19
Mon 1/26
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 December 20, 2025.

This Expedia deal was found by Cheapflights users on 12/19. 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.
Sun 12/213:26 pmORD - SXM
1 stop20h 49mSpirit Airlines
Mon 12/293:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 12/19$449
This Delta deal was found by Cheapflights users on 12/19. 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 12/215:30 amORD - SXM
1 stop7h 20mDelta
Thu 12/251:45 pmSXM - ORD
1 stop12h 17mDelta
Deal found 12/19$501
This Delta deal was found by Cheapflights users on 12/18. 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 12/217:59 pmORD - SXM
1 stop16h 51mDelta
Wed 12/314:15 pmSXM - ORD
2 stops29h 23mDelta
Deal found 12/18$506
This Air Canada deal was found by Cheapflights users on 12/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/223:35 pmORD - SXM
1 stop21h 05mAir Canada
Thu 12/253:40 pmSXM - ORD
2 stops29h 13mAir Canada
Deal found 12/19$521
This Delta deal was found by Cheapflights users on 12/19. 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 12/215:30 amORD - SXM
1 stop7h 20mDelta
Mon 12/291:45 pmSXM - ORD
1 stop12h 17mDelta
Deal found 12/19$531
This Delta deal was found by Cheapflights users on 12/18. 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.
Sat 12/206:02 pmORD - SXM
2 stops18h 48mDelta
Tue 12/304:15 pmSXM - ORD
2 stops27h 07mDelta
Deal found 12/18$536
This Air Canada deal was found by Cheapflights users on 12/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:30 pmORD - SXM
2 stops40h 10mAir Canada
Thu 12/253:40 pmSXM - ORD
1 stop25h 15mAir Canada
Deal found 12/19$550
This Delta deal was found by Cheapflights users on 12/18. 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.
Sat 12/207:55 pmORD - SXM
1 stop16h 55mDelta
Mon 12/291:45 pmSXM - ORD
1 stop12h 17mDelta
Deal found 12/18$561
This Cheapflightsfares deal was found by Cheapflights users on 12/18. 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.
Wed 12/245:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Mon 12/293:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 12/18$585
This United Airlines deal was found by Cheapflights users on 12/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Thu 12/254:55 pmSXM - ORD
1 stop16h 52mUnited Airlines
Deal found 12/19$607
This United Airlines deal was found by Cheapflights users on 12/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:15 pmORD - SXM
1 stop14h 35mUnited Airlines
Wed 12/314:55 pmSXM - ORD
1 stop16h 53mUnited Airlines
Deal found 12/18$611
This Mytrip deal was found by Cheapflights users on 12/18. 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.
Mon 12/224:30 pmMSP - SXM
1 stop21h 30mAir Canada
Wed 12/245:00 pmSXM - MSP
1 stop30h 19mAir Canada
Deal found 12/18$708

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 December 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$211
(FlightHub)

One-way from

$70
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$866
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.
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From Wisconsin to St. Maarten
Search Deals
One-way flight from Wisconsin to St. Maarten
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($268 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($103 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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 December 20, 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

Mon 2/9

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Wed 2/18

3:20 pm-11:47 pm

1 stop10h 27m

$224

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/19

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 1/23

3:15 pm-11:46 pm

1 stop10h 31m

$245

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sun 2/1

3:20 pm-11:47 pm

1 stop10h 27m

$289

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/16

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Tue 1/20

3:40 pm-8:05 am

1 stop18h 25m

$306

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/18

1:13 pm-2:10 pm

1 stop22h 57m

Simpson Bay Princess Juliana

Sun 1/25

3:15 pm-10:41 am

2 stops21h 26m

$313

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/14

12:06 pm-2:15 pm

1 stop24h 09m

Simpson Bay Princess Juliana

Sat 2/21

3:20 pm-11:47 pm

1 stop10h 27m

$318

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/10

12:44 pm-2:10 pm

3 stops23h 26m

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-9:12 am

2 stops19h 57m

$344

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/6

10:07 am-2:15 pm

2 stops26h 08m

Simpson Bay Princess Juliana

Sun 2/8

3:20 pm-9:12 am

2 stops19h 52m

$350

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/17

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 1/24

6:32 pm-10:51 pm

Nonstop6h 19m

$455

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 2/7

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 2/14

6:32 pm-10:51 pm

Nonstop6h 19m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 50 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, March is the cheapest month in which you can book a flight from Wisconsin to St. Maarten (average of $584). Flying from Wisconsin to St. Maarten in November is currently the most expensive (average of $649). 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 December 20, 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 $455, Spirit Airlines can have you in St. Maarten from Wisconsin in 5h 24m. 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, March is the cheapest month in which you can book a flight from Wisconsin to St. Maarten (average of $584). Flying from Wisconsin to St. Maarten in November is currently the most expensive (average of $649). 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

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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 December 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$584Average$760FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$587Average$793FlexibilityNo cancel feeOn-time71%

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