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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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 August 1, 2025.

Round-trip from

$312
(Booking.com)

One-way from

$139
(Cheapflightsfares)

Popular in

June

Cheapest in

May
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 ($264 potential increase over avg. RT price).
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Cheapest flight prices on average. 16% potential price decrease ($117 potential savings vs. average RT price).
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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 August 1, 2025.

This Booking.com deal was found by Cheapflights users on 7/30. 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.
Sat 9/65:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 9/133:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 7/30$312
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/186:56 amORD - SXM
2 stops9h 25mMultiple Airlines
Wed 8/273:05 pmSXM - ORD
1 stop9h 54mMultiple Airlines
Deal found 7/30$414
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:00 amMKE - SXM
1 stop6h 56mDelta
Sun 9/73:21 pmSXM - MKE
1 stop9h 15mDelta
Deal found 8/1$497
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/279:31 amMSP - SXM
2 stops51h 29mSpirit Airlines
Fri 10/33:05 pmSXM - MSP
2 stops18h 21mSpirit Airlines
Deal found 7/30$508
This Delta deal was found by Cheapflights users on 7/31. 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.
Sun 9/75:34 amATW - SXM
1 stop7h 22mDelta
Sun 9/143:20 pmSXM - ATW
1 stop8h 20mDelta
Deal found 7/31$612
This American Airlines deal was found by Cheapflights users on 8/1. 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.
Sat 9/274:35 pmGRB - SXM
2 stops19h 44mAmerican Airlines
Sat 10/42:40 pmSXM - GRB
2 stops19h 38mAmerican Airlines
Deal found 8/1$617
This Delta deal was found by Cheapflights users on 7/30. 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 9/44:57 pmMSN - SXM
2 stops19h 48mDelta
Wed 9/103:10 pmSXM - MSN
2 stops25h 59mDelta
Deal found 7/30$617
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 10/295:47 pmMKE - SXM
2 stops20h 28mAmerican Airlines
Wed 11/53:20 pmSXM - MKE
2 stops22h 00mAmerican Airlines
Deal found 7/30$617
This United Airlines deal was found by Cheapflights users on 7/31. 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 11/12:45 pmMKE - SXM
1 stop24h 12mUnited Airlines
Sat 11/82:51 pmSXM - MKE
1 stop28h 26mUnited Airlines
Deal found 7/31$619
This Justfly.com deal was found by Cheapflights users on 7/31. 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.
Tue 12/21:39 pmMSP - SXM
2 stops23h 31mMultiple Airlines
Thu 12/113:40 pmSXM - MSP
2 stops26h 09mMultiple Airlines
Deal found 7/31$635
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 9/266:18 pmATW - SXM
2 stops18h 22mAmerican Airlines
Sat 10/42:40 pmSXM - ATW
2 stops19h 26mAmerican Airlines
Deal found 7/31$642
This Delta deal was found by Cheapflights users on 7/31. 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.
Sun 12/78:15 pmMSP - SXM
1 stop16h 20mDelta
Sat 12/203:40 pmSXM - MSP
Nonstop6h 25mDelta
Deal found 7/31$709

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 August 1, 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 9/6

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:48 pm

1 stop8h 43m

$312

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 8/18

6:56 am-5:21 pm

2 stops9h 25m

Simpson Bay Princess Juliana

Wed 8/27

3:05 pm-11:59 pm

1 stop9h 54m

$414

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/10

10:08 am-5:32 pm

Nonstop5h 24m

Simpson Bay Princess Juliana

Sat 1/17

6:32 pm-10:51 pm

Nonstop6h 19m

$486

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 9/14

5:40 am-1:50 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Sun 9/21

3:20 pm-11:48 pm

1 stop9h 28m

$497

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 9/27

9:31 am-2:00 pm

2 stops51h 29m

Simpson Bay Princess Juliana

Fri 10/3

3:05 pm-8:26 am

2 stops18h 21m

$508

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Sat 1/3

4:30 pm-2:40 pm

2 stops20h 10m

Simpson Bay Princess Juliana

Sat 1/10

6:32 pm-10:51 pm

Nonstop6h 19m

$559

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Sat 1/24

3:49 pm-2:05 pm

2 stops20h 16m

Simpson Bay Princess Juliana

Thu 1/29

3:25 pm-11:42 pm

1 stop10h 17m

$592

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Sun 9/7

5:34 am-1:56 pm

1 stop7h 22m

Simpson Bay Princess Juliana

Sun 9/14

3:20 pm-10:40 pm

1 stop8h 20m

$612

Green BaySimpson Bay

GRB - SXM

GRBSXM

Green Bay Austin-Straubel

Sat 9/27

4:35 pm-1:19 pm

2 stops19h 44m

Simpson Bay Princess Juliana

Sat 10/4

2:40 pm-9:18 am

2 stops19h 38m

$617

MadisonSimpson Bay

MSN - SXM

MSNSXM

Madison Truax Field

Thu 9/4

4:57 pm-1:45 pm

2 stops19h 48m

Simpson Bay Princess Juliana

Wed 9/10

3:10 pm-4:09 pm

2 stops25h 59m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 35 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 $655). 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 August 1, 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.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. 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 Simpson Bay. Reviews last updated August 1, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Wisconsin to Simpson Bay to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,978 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,851 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 $139. However, be on the lookout for offers from Frontier and Air Canada, 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, 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 $655). 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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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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$504Average$784FlexibilityNo cancel feeOn-time71%
DeltaCheapest$514Average$680FlexibilityNo cancel feeOn-timeN/A

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