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Simpson Bay

$72+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
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 February 6, 2026.

This Booking.com deal was found by Cheapflights users on 2/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/165:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Thu 2/193:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/3$249
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 3/48:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Mon 3/92:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/3$251
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Wed 2/185:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/253:20 pm
SXM
-
ORD
1 stop22h 02m
Spirit Airlines
Deal found 2/3$271
This Priceline deal was found by Cheapflights users on 2/4. 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.
Wed 3/45:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Tue 3/102:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/4$276
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 2/288:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Sat 3/73:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/3$283
This Priceline deal was found by Cheapflights users on 2/4. 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 3/78:16 pm
ORD
-
SXM
1 stop14h 59m
Spirit Airlines
Sat 3/142:20 pm
SXM
-
ORD
1 stop9h 57m
Spirit Airlines
Deal found 2/4$284
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 2/95:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/183:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/3$289
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/166:42 am
MSP
-
SXM
1 stop29h 33m
Multiple Airlines
Thu 2/263:20 pm
SXM
-
MSP
2 stops30h 05m
Multiple Airlines
Deal found 2/3$441
This Mytrip deal was found by Cheapflights users on 2/3. 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.
Sat 4/410:01 am
MSP
-
SXM
Nonstop5h 31m
Multiple Airlines
Sat 4/112:35 pm
SXM
-
MSP
2 stops21h 37m
Multiple Airlines
Deal found 2/3$456
This Sun Country Air deal was found by Cheapflights users on 2/3. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:08 am
MSP
-
SXM
Nonstop5h 24m
Sun Country Air
Sat 2/146:32 pm
SXM
-
MSP
Nonstop6h 19m
Sun Country Air
Deal found 2/3$462
This Mytrip deal was found by Cheapflights users on 2/4. 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.
Sat 2/2110:01 am
MSP
-
SXM
Nonstop5h 31m
Multiple Airlines
Sat 2/283:20 pm
SXM
-
MSP
2 stops20h 30m
Multiple Airlines
Deal found 2/4$468
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/154:36 pm
MSP
-
SXM
1 stop19h 39m
Multiple Airlines
Thu 2/263:20 pm
SXM
-
MSP
2 stops30h 05m
Multiple Airlines
Deal found 2/4$483

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 February 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Booking.com)

One-way from

$72
(Super.com)

Popular in

June

Cheapest in

August

Average price

$857
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. 24% potential increase in price ($286 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($101 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 6, 2026.
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 3/4

10:19 am-2:15 pm

2 stops25h 56m

Simpson Bay Princess Juliana

Mon 3/9

2:20 pm-11:47 pm

1 stop10h 27m

$310

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/10

6:10 pm-1:30 pm

1 stop18h 20m

Simpson Bay Princess Juliana

Wed 4/15

2:11 pm-11:41 pm

1 stop10h 30m

$314

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/11

5:15 am-1:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 3/16

2:20 pm-11:17 am

1 stop21h 57m

$332

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 5/26

5:15 am-1:16 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Wed 6/3

2:11 pm-11:41 pm

1 stop10h 30m

$340

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/5

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Mon 3/9

2:20 pm-11:47 pm

1 stop10h 27m

$343

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 3/31

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Mon 4/6

4:00 pm-12:17 pm

2 stops21h 17m

$344

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/25

1:35 pm-1:16 pm

2 stops22h 41m

Simpson Bay Princess Juliana

Sat 5/9

2:11 pm-11:41 pm

1 stop10h 30m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/24

3:10 pm-1:16 pm

2 stops21h 06m

Simpson Bay Princess Juliana

Tue 4/28

2:11 pm-11:41 pm

1 stop10h 30m

$359

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/20

4:42 pm-1:59 pm

1 stop19h 17m

Simpson Bay Princess Juliana

Tue 2/24

3:20 pm-11:47 pm

1 stop10h 27m

$365

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/4

10:44 am-2:15 pm

3 stops25h 31m

Simpson Bay Princess Juliana

Wed 3/11

2:20 pm-10:20 am

2 stops21h 00m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

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, February is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $577). Flying from Wisconsin to Simpson Bay in June is currently the most expensive (average of $754). 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.

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, Sun Country Air, and Delta fly from Wisconsin to Simpson Bay in about 5h 31m. The time it takes to get you to your destination can typically vary by up to 20h 25m. 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, February is the cheapest month in which you can book a flight from Wisconsin to Simpson Bay (average of $577). Flying from Wisconsin to Simpson Bay in June is currently the most expensive (average of $754). 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 February 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$605Average$832FlexibilityNo cancel feeOn-time71%
DeltaCheapest$609Average$747FlexibilityNo cancel feeOn-timeN/A

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