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Simpson Bay

$139+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$337
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$612
From Wisconsin to Simpson Bay Princess Juliana
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One-way flight from Wisconsin to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 24% potential increase in price ($280 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease ($114 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Wed 11/54:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 9/15$337
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/185:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 9/14$342
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Fri 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 9/16$346
This Priceline deal was found by Cheapflights users on 9/14. 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 11/85:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Sat 11/154:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 9/14$347
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:00 pmORD - SXM
1 stop24h 00mMultiple Airlines
Wed 12/104:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/15$373
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Wed 10/291:59 pmORD - SXM
2 stops48h 01mMultiple Airlines
Wed 11/54:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/14$383
This Orbitz deal was found by Cheapflights users on 9/14. 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 Orbitz 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
Wed 12/34:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/14$393
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Sat 11/13:05 pmSXM - ORD
1 stop21h 45mSpirit Airlines
Deal found 9/15$398
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 10/313:05 pmSXM - ORD
1 stop28h 33mSpirit Airlines
Deal found 9/16$400
This Gotogate deal was found by Cheapflights users on 9/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:43 pmORD - SXM
1 stop17h 17mMultiple Airlines
Fri 10/314:00 pmSXM - ORD
2 stops17h 00mMultiple Airlines
Deal found 9/16$401
This Gotogate deal was found by Cheapflights users on 9/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:43 pmORD - SXM
1 stop17h 17mMultiple Airlines
Sat 11/14:00 pmSXM - ORD
2 stops21h 18mMultiple Airlines
Deal found 9/15$402
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/316:39 pmMKE - SXM
1 stop19h 18mUnited Airlines
Tue 11/42:52 pmSXM - MKE
2 stops22h 37mUnited Airlines
Deal found 9/14$527

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 September 16, 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

Sat 2/21

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:35 pm

1 stop9h 05m

$375

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/31

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 2/7

6:32 pm-10:51 pm

Nonstop6h 19m

$455

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

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/17

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 1/31

6:32 pm-10:51 pm

Nonstop6h 19m

$455

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/24

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 1/31

6:32 pm-10:51 pm

Nonstop6h 19m

$455

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/8

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 11/15

4:28 pm-7:13 am

2 stops16h 45m

$467

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/26

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 1/30

4:28 pm-9:23 am

1 stop18h 55m

$468

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

6:28 pm-4:00 pm

1 stop19h 32m

Simpson Bay Princess Juliana

Mon 12/15

5:00 pm-11:18 am

2 stops20h 18m

$483

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

2:13 pm-11:24 am

1 stop19h 11m

Simpson Bay Princess Juliana

Sun 2/1

12:25 pm-12:04 am

1 stop13h 39m

$489

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 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, September is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $459). Flying from Wisconsin to Simpson Bay in March is currently the most expensive (average of $652). 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Simpson Bay as you normally would.

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 Sun Country Air, Spirit Airlines, and Air Canada 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 14h 08m. The distance between Wisconsin and Simpson Bay is about 2536 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 Air Canada, with whom users have recently found tickets for as low as $141. However, be on the lookout for offers from Spirit Airlines 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 Appleton Intl - 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, September is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $459). Flying from Wisconsin to Simpson Bay in March is currently the most expensive (average of $652). 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$572Average$686FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$584Average$800FlexibilityNo cancel feeOn-time71%

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