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$199+ Cheap flights from Simpson Bay (SXM) to Wisconsin

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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MKE
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Simpson Bay to Wisconsin

Keep the following information in mind while searching for Simpson Bay to Wisconsin flight deals. Data was last updated September 16, 2025.

Round-trip from

$329
(Gotogate)

One-way from

$199
(Cheapflightsfares)
From Simpson Bay Princess Juliana to Wisconsin
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One-way flight from Simpson Bay Princess Juliana to Wisconsin
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Find flight deals from Simpson Bay to Wisconsin

Cheapest flights from Simpson Bay to Wisconsin
Explore the most affordable flight options available from Simpson Bay to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Fri 10/177:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Deal found 9/14$329
This Spirit deal was found by Cheapflights users on 9/13. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Sat 12/135:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Deal found 9/13$437
This Flightnetwork deal was found by Cheapflights users on 9/13. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/63:40 pmSXM - ORD
1 stop21h 38mAir Canada
Sat 12/136:05 pmORD - SXM
2 stops43h 55mAir Canada
Deal found 9/13$452
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:44 pmSXM - ORD
1 stop29h 08mJetBlue
Wed 11/126:44 amORD - SXM
1 stop7h 54mJetBlue
Deal found 9/15$460
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.
Fri 10/33:05 pmSXM - ORD
1 stop8h 43mMultiple Airlines
Wed 10/86:58 pmORD - SXM
2 stops39h 29mMultiple Airlines
Deal found 9/15$496
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:51 pmSXM - ORD
1 stop10h 49mAmerican Airlines
Wed 11/127:00 amORD - SXM
1 stop7h 22mAmerican Airlines
Deal found 9/15$503

Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Wisconsin 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 Simpson Bay to Wisconsin that are best for you.

Fly from

Simpson Bay

Fly to

Wisconsin

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 10/11

3:05 pm-11:45 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 10/17

7:43 pm-2:00 pm

1 stop17h 17m

$329

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

3:40 pm-11:18 am

1 stop21h 38m

Chicago O'Hare Intl

Sat 12/13

6:05 pm-4:00 pm

2 stops43h 55m

$452

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 11/6

5:44 pm-8:52 pm

1 stop29h 08m

Chicago O'Hare Intl

Wed 11/12

6:44 am-4:38 pm

1 stop7h 54m

$460

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 10/3

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

Wed 10/8

6:58 pm-11:27 am

2 stops39h 29m

$496

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 11/6

2:51 pm-11:40 pm

1 stop10h 49m

Chicago O'Hare Intl

Wed 11/12

7:00 am-4:22 pm

1 stop7h 22m

$503

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/15

4:28 pm-11:42 pm

1 stop9h 14m

$199

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/13

4:30 pm-12:08 am

1 stop9h 38m

$229

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 12/11

3:40 pm-12:51 pm

2 stops23h 11m

$231

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/14

4:28 pm-11:42 pm

1 stop9h 14m

$231

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 11/16

12:25 pm-12:30 pm

2 stops26h 05m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 13 results
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Best time to book a flight from Simpson Bay to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Simpson Bay 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 Simpson Bay to Wisconsin
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Wisconsin. 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 from for flights from Simpson Bay to Wisconsin?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana (SXM) is the airport most travelers will use when flying to Wisconsin from Simpson Bay.

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

    Departing from Simpson Bay to Wisconsin will take you 9h 40m. There are 2204 mi between Simpson Bay and Wisconsin. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $199. Users have also found prices from $229 and $231 on Frontier and Air Canada, respectively.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Simpson Bay to Wisconsin (average of $280). Flying from Simpson Bay to Wisconsin in June is currently the most expensive (average of $376). 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.

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