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Simpson Bay

$125+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find 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 November 3, 2025.

This Expedia deal was found by Cheapflights users on 11/1. 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 11/295:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/63:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/1$302
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/1$315
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Sat 12/62:40 pmSXM - ORD
Nonstop6h 00mUnited Airlines
Deal found 11/1$361
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:02 pmORD - SXM
1 stop16h 53mDelta
Sat 12/63:25 pmSXM - ORD
1 stop9h 18mDelta
Deal found 11/2$365
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:35 pmORD - SXM
1 stop17h 17mAmerican Airlines
Thu 12/181:39 pmSXM - ORD
1 stop13h 04mAmerican Airlines
Deal found 11/1$375
This Expedia deal was found by Cheapflights users on 11/1. 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 11/295:55 pmORD - SXM
2 stops44h 05mMultiple Airlines
Sat 12/63:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 11/1$377
This Mytrip deal was found by Cheapflights users on 11/1. 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 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 11/1$378
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:07 pmORD - SXM
1 stop17h 13mAmerican Airlines
Sun 12/211:39 pmSXM - ORD
1 stop13h 04mAmerican Airlines
Deal found 11/2$380
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fri 1/94:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 11/2$389
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 1/104:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 11/2$390
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/282:42 pmMSP - SXM
2 stops21h 33mMultiple Airlines
Sat 12/63:20 pmSXM - MSP
2 stops24h 40mMultiple Airlines
Deal found 11/1$501
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:12 amMSP - SXM
2 stops30h 03mMultiple Airlines
Tue 12/231:45 pmSXM - MSP
1 stop9h 33mMultiple Airlines
Deal found 11/1$564

Cheap 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$302
(Expedia)

One-way from

$125
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$700
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. 25% potential increase in price ($287 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($116 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 3, 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

Wed 1/28

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 2/6

4:28 pm-11:42 pm

1 stop9h 14m

$313

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/29

8:02 pm-2:55 pm

1 stop16h 53m

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-1:50 pm

2 stops24h 25m

$365

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sat 12/6

5:00 pm-11:43 pm

1 stop8h 43m

$371

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

6:35 pm-1:52 pm

1 stop17h 17m

Simpson Bay Princess Juliana

Thu 12/18

1:39 pm-12:43 am

1 stop13h 04m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 12/16

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-12:02 am

1 stop12h 17m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/4

6:15 pm-12:30 pm

1 stop16h 15m

Simpson Bay Princess Juliana

Mon 1/12

4:20 pm-9:44 am

1 stop19h 24m

$381

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/5

5:33 am-2:55 pm

1 stop7h 22m

Simpson Bay Princess Juliana

Mon 1/12

4:20 pm-10:59 am

2 stops20h 39m

$386

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/21

3:26 pm-2:15 pm

1 stop20h 49m

Simpson Bay Princess Juliana

Wed 1/7

3:20 pm-7:24 pm

1 stop30h 04m

$396

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/29

5:00 am-4:22 pm

1 stop9h 22m

Simpson Bay Princess Juliana

Sat 12/6

4:00 pm-7:54 pm

Nonstop5h 54m

$400

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/27

9:09 pm-2:15 pm

2 stops39h 06m

Simpson Bay Princess Juliana

Wed 1/7

3:20 pm-7:24 pm

1 stop30h 04m

$438

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 56 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, January is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $566). Flying from Wisconsin to Simpson Bay 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 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 November 3, 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, Delta, and United Airlines fly from Wisconsin to Simpson Bay in about 5h 12m. The time it takes to get you to your destination can typically vary by up to 11h 41m. The distance between Wisconsin and Simpson Bay is about 2204 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Wisconsin to Simpson Bay one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $145. However, be on the lookout for offers from Sun Country Air and American Airlines, as they are both options that can get you from Wisconsin to Simpson Bay for a low price.

  • 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, January is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $566). Flying from Wisconsin to Simpson Bay 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

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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$584Average$707FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$605Average$800FlexibilityNo cancel feeOn-time71%

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