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St. Maarten

$183+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$338
(Priceline)

One-way from

$183
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$1,093
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. 21% potential increase in price ($216 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($75 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Mon 6/25:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 6/93:05 pmSXM - ORD
1 stop18h 45mSpirit Airlines
Deal found 4/29$333
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/65:08 pmORD - SXM
1 stop17h 15mMultiple Airlines
Sat 6/143:05 pmSXM - ORD
1 stop18h 45mMultiple Airlines
Deal found 4/29$383
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/65:08 pmORD - SXM
1 stop17h 15mFrontier
Sat 6/1412:36 pmSXM - ORD
2 stops22h 46mFrontier
Deal found 4/29$428
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Tue 6/247:54 amMSP - SXM
2 stops29h 06mMultiple Airlines
Fri 6/273:05 pmSXM - MSP
2 stops29h 41mMultiple Airlines
Deal found 4/28$530
This Mytrip deal was found by Cheapflights users on 4/29. 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 6/133:00 pmMKE - SXM
2 stops22h 00mSpirit Airlines
Fri 6/203:05 pmSXM - MKE
2 stops28h 04mSpirit Airlines
Deal found 4/29$572
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:48 pmMKE - SXM
2 stops19h 22mAmerican Airlines
Wed 12/104:45 pmSXM - MKE
2 stops21h 51mAmerican Airlines
Deal found 4/29$592
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/129:46 amATW - SXM
2 stops26h 39mAmerican Airlines
Sat 7/194:25 pmSXM - ATW
2 stops19h 04mAmerican Airlines
Deal found 4/29$617
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/106:00 amORD - SXM
1 stop8h 05mAmerican Airlines
Tue 6/172:34 pmSXM - ORD
1 stop8h 55mAmerican Airlines
Deal found 4/29$622
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:00 amORD - SXM
1 stop7h 41mJetBlue
Sat 8/2312:15 pmSXM - ORD
1 stop12h 10mJetBlue
Deal found 4/29$635
This Justfly.com deal was found by Cheapflights users on 4/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:25 pmORD - SXM
2 stops17h 30mAir Canada
Sun 12/144:55 pmSXM - ORD
2 stops20h 03mAir Canada
Deal found 4/29$679
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/205:35 amMKE - SXM
1 stop7h 25mDelta
Wed 6/253:25 pmSXM - MKE
1 stop9h 32mDelta
Deal found 4/29$707
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:15 amMSP - SXM
1 stop7h 33mDelta
Wed 9/103:15 pmSXM - MSP
1 stop10h 07mDelta
Deal found 4/29$709

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 April 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

Mon 6/2

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 6/9

3:05 pm-8:50 am

1 stop18h 45m

$333

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 6/6

5:08 pm-11:23 am

1 stop17h 15m

Simpson Bay Princess Juliana

Sat 6/14

3:05 pm-8:50 am

1 stop18h 45m

$383

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 6/6

5:08 pm-11:23 am

1 stop17h 15m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-10:22 am

2 stops22h 46m

$428

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Tue 6/24

7:54 am-2:00 pm

2 stops29h 06m

Simpson Bay Princess Juliana

Fri 6/27

3:05 pm-7:46 pm

2 stops29h 41m

$530

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 6/13

3:00 pm-2:00 pm

2 stops22h 00m

Simpson Bay Princess Juliana

Fri 6/20

3:05 pm-6:09 pm

2 stops28h 04m

$572

Green BaySimpson Bay

GRB - SXM

GRBSXM

Green Bay Austin-Straubel

Fri 6/13

5:53 pm-3:05 pm

2 stops20h 12m

Simpson Bay Princess Juliana

Fri 6/20

2:34 pm-9:23 am

2 stops19h 49m

$617

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Sat 7/12

9:46 am-1:25 pm

2 stops26h 39m

Simpson Bay Princess Juliana

Sat 7/19

4:25 pm-10:29 am

2 stops19h 04m

$617

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 6/20

4:21 pm-1:34 pm

2 stops20h 13m

Simpson Bay Princess Juliana

Wed 6/25

2:34 pm-12:36 pm

2 stops23h 02m

$617

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 6/10

6:00 am-3:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Tue 6/17

2:34 pm-10:29 pm

1 stop8h 55m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/16

6:00 am-2:41 pm

1 stop7h 41m

Simpson Bay Princess Juliana

Sat 8/23

12:15 pm-11:25 pm

1 stop12h 10m

$635

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 23 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 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 April 30, 2025.

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.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St. Maarten. Reviews last updated April 30, 2025.
To help decide which airline to fly from Wisconsin to St. Maarten, see what other customers have to say about Delta, United Airlines and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
JetBlue
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Spirit Airlines
6.3
Okay
7,961 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • 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, September is the cheapest month in which you can book a flight from Wisconsin to St. Maarten (average of $459). Flying from Wisconsin to St. Maarten in July is currently the most expensive (average of $675). 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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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$469Average$786FlexibilityNo cancel feeOn-time71%
DeltaCheapest$479Average$811FlexibilityNo cancel feeOn-timeN/A

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