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Simpson Bay

$71+ Cheap flights from Wisconsin to Simpson Bay (SXM)

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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Wisconsin to Simpson Bay

Cheapest flights from Wisconsin to Simpson Bay
Explore the most affordable flight options available from Wisconsin to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/16. 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 12/205:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/273:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 12/16$438
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 12/17$475
This United Airlines deal was found by Cheapflights users on 12/17. 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
Tue 12/234:55 pmSXM - ORD
1 stop8h 49mUnited Airlines
Deal found 12/17$497
This Priceline deal was found by Cheapflights users on 12/15. 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.
Fri 12/196:00 amORD - SXM
1 stop29h 30mMultiple Airlines
Sun 12/213:40 pmSXM - ORD
1 stop21h 38mMultiple Airlines
Deal found 12/15$520
This Delta deal was found by Cheapflights users on 12/17. 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.
Tue 12/235:30 amORD - SXM
1 stop7h 20mDelta
Mon 12/291:45 pmSXM - ORD
1 stop9h 29mDelta
Deal found 12/17$531
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Fri 12/196:00 amORD - SXM
1 stop7h 51mUnited Airlines
Sun 12/212:20 pmSXM - ORD
Nonstop6h 01mUnited Airlines
Deal found 12/15$551
This KAYAK deal was found by Cheapflights users on 12/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:44 pmORD - SXM
2 stops16h 31mSpirit Airlines
Mon 12/293:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 12/17$554
This Expedia deal was found by Cheapflights users on 12/17. 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 12/217:41 pmORD - SXM
1 stop15h 03mMultiple Airlines
Tue 12/233:40 pmSXM - ORD
1 stop29h 10mMultiple Airlines
Deal found 12/17$556
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/185:30 amORD - SXM
1 stop7h 20mDelta
Sun 12/211:45 pmSXM - ORD
1 stop9h 29mDelta
Deal found 12/16$561
This Gotogate deal was found by Cheapflights users on 12/17. 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.
Sun 12/218:30 pmORD - SXM
2 stops40h 10mAir Canada
Tue 12/235:00 pmSXM - ORD
2 stops27h 53mAir Canada
Deal found 12/17$568
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/255:15 amMSP - SXM
1 stop7h 35mDelta
Wed 12/311:45 pmSXM - MSP
1 stop12h 48mDelta
Deal found 12/17$685
This Delta deal was found by Cheapflights users on 12/17. 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.
Mon 12/295:15 amMSP - SXM
1 stop7h 35mDelta
Wed 12/314:15 pmSXM - MSP
2 stops21h 49mDelta
Deal found 12/17$690

Find flight deals from Wisconsin to Simpson Bay

Keep the following information in mind while searching for Wisconsin to Simpson Bay flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$223
(Super.com)

One-way from

$71
(Cheapflightsfares)

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.
Search Deals
From Wisconsin to Simpson Bay Princess Juliana
Search Deals
One-way flight from Wisconsin to Simpson Bay Princess Juliana
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).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Simpson Bay 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 18, 2025.
Use the filters below to find and compare flights from Wisconsin to Simpson Bay that are best for you.

Fly from

Wisconsin

Fly to

Simpson Bay

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 2/17

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Thu 2/26

3:20 pm-11:47 pm

1 stop10h 27m

$246

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Fri 2/13

3:20 pm-7:50 pm

1 stop30h 30m

$249

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/6

8:43 pm-2:15 pm

1 stop15h 32m

Simpson Bay Princess Juliana

Thu 2/12

3:20 pm-11:24 pm

1 stop10h 04m

$249

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/8

3:00 pm-2:15 pm

1 stop21h 15m

Simpson Bay Princess Juliana

Thu 2/12

3:20 pm-11:24 pm

1 stop10h 04m

$253

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 2/9

3:20 pm-11:47 pm

1 stop10h 27m

$257

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 2/4

5:32 pm-2:15 pm

1 stop18h 43m

Simpson Bay Princess Juliana

Thu 2/12

3:20 pm-11:24 pm

1 stop10h 04m

$261

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/23

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Thu 1/29

3:15 pm-11:27 am

2 stops22h 12m

$285

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 2/17

6:02 pm-2:15 pm

2 stops18h 13m

Simpson Bay Princess Juliana

Wed 2/25

3:20 pm-11:47 pm

1 stop10h 27m

$289

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

3:15 pm-11:46 pm

1 stop10h 31m

$317

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 2/14

3:15 pm-2:23 pm

2 stops25h 08m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 47 results
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Best time to book a flight from Wisconsin to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay 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 Simpson Bay

What is the cheapest month to book a flight from Wisconsin to Simpson Bay?

Currently, March is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $584). Flying from Wisconsin to Simpson Bay 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 SXM?

Find hourly flight availability from Wisconsin to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

When flying from Wisconsin to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 25% versus a flight in the evening.

How much does it cost to fly round-trip from Wisconsin to Simpson Bay?

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Simpson Bay from Wisconsin?

    Simpson Bay Princess Juliana (SXM), located 0.5 mi from the city center, is the airport you fly into when you book flights from Wisconsin to Simpson Bay.

  • How long is the flight from Wisconsin to Simpson Bay?

    Airlines like Spirit Airlines and Sun Country Air fly from Wisconsin to Simpson Bay in about 5h 24m. The time it takes to get you to your destination can typically vary by up to 1h 36m. The distance between Wisconsin and Simpson Bay is about 2536 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Wisconsin to Simpson Bay?

    When deciding which route to take from Wisconsin to Simpson Bay consider Chicago O'Hare Intl - Simpson Bay Princess Juliana, Minneapolis St Paul - Simpson Bay Princess Juliana or Milwaukee-Mitchell - Simpson Bay Princess Juliana as they are the most popular.

  • Can I find deals for flights from Wisconsin to Simpson Bay that include hotel bookings?

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

  • How can I find direct flights from Wisconsin to Simpson Bay?

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

  • Can I find deals for business class flights from Wisconsin to Simpson Bay?

    Yes. Cheapflights offers flight deals from Wisconsin to Simpson Bay 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 Simpson Bay?

    Currently, March is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $584). Flying from Wisconsin to Simpson Bay 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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Alternative routes for Wisconsin to Simpson Bay

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 Simpson Bay

Discover the top 2 airlines that operate flights from Wisconsin to Simpson Bay. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$584Average$708FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$587Average$793FlexibilityNo cancel feeOn-time71%

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