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$156+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MKE
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap 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 February 5, 2026.

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 2/143:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Sat 2/215:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Deal found 2/3$258
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.
Thu 5/72:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Sun 5/105:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 2/3$349
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:11 pm
SXM
-
ORD
1 stop9h 46m
Multiple Airlines
Sun 5/101:27 pm
ORD
-
SXM
1 stop22h 49m
Multiple Airlines
Deal found 2/2$362
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Sun 5/105:32 pm
ORD
-
SXM
1 stop18h 44m
Spirit Airlines
Deal found 2/4$371
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Thu 3/192:20 pm
SXM
-
ORD
1 stop9h 57m
Multiple Airlines
Thu 3/261:55 pm
ORD
-
SXM
1 stop24h 05m
Multiple Airlines
Deal found 2/1$439
This Mytrip deal was found by Cheapflights users on 2/1. 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.
Thu 3/192:20 pm
SXM
-
ORD
1 stop9h 57m
Spirit Airlines
Thu 3/263:21 pm
ORD
-
SXM
2 stops20h 54m
Spirit Airlines
Deal found 2/1$461
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:11 pm
SXM
-
ORD
3 stops34h 01m
Spirit Airlines
Sun 5/105:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 2/2$513
This American Airlines deal was found by Cheapflights users on 2/2. 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 5/72:21 pm
SXM
-
MSN
2 stops21h 51m
American Airlines
Sun 5/108:24 pm
MSN
-
SXM
2 stops15h 57m
American Airlines
Deal found 2/2$620
This Delta deal was found by Cheapflights users on 2/5. 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 5/73:20 pm
SXM
-
MSN
2 stops18h 29m
Delta
Mon 5/115:43 am
MSN
-
SXM
1 stop7h 16m
Delta
Deal found 2/5$735
This American Airlines deal was found by Cheapflights users on 2/5. 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 5/74:35 pm
SXM
-
MSN
2 stops20h 55m
American Airlines
Mon 5/118:24 pm
MSN
-
SXM
2 stops15h 57m
American Airlines
Deal found 2/5$748

Find 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 February 5, 2026.

Round-trip from

$349
(Cheapflightsfares)

One-way from

$156
(Expedia)
From Simpson Bay Princess Juliana to Wisconsin
Search Deals
One-way flight from Simpson Bay Princess Juliana to Wisconsin
Search Deals

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 February 5, 2026.
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

Thu 5/7

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 5/10

5:15 am-1:16 pm

1 stop7h 01m

$349

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 5/8

2:11 pm-10:57 pm

1 stop9h 46m

Chicago O'Hare Intl

Sun 5/10

1:27 pm-1:16 pm

1 stop22h 49m

$362

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 5/6

2:11 pm-11:41 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 5/10

5:32 pm-1:16 pm

1 stop18h 44m

$371

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 3/19

2:20 pm-11:17 pm

1 stop9h 57m

Chicago O'Hare Intl

Thu 3/26

1:55 pm-3:00 pm

1 stop24h 05m

$439

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 3/19

2:20 pm-11:17 pm

1 stop9h 57m

Chicago O'Hare Intl

Thu 3/26

3:21 pm-1:15 pm

2 stops20h 54m

$461

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 5/8

2:11 pm-11:12 pm

3 stops34h 01m

Chicago O'Hare Intl

Sun 5/10

5:15 am-1:16 pm

1 stop7h 01m

$513

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/7

3:20 pm-7:58 am

2 stops17h 38m

Chicago O'Hare Intl

Sun 5/10

6:00 am-1:59 pm

1 stop6h 59m

$606

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 5/7

2:24 pm-11:55 pm

1 stop10h 31m

Madison Truax Field

Sun 5/10

8:24 pm-3:22 pm

2 stops17h 58m

$620

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 5/7

3:20 pm-8:49 am

2 stops18h 29m

Madison Truax Field

Mon 5/11

5:43 am-1:59 pm

1 stop7h 16m

$735

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 5/7

4:35 pm-12:30 pm

2 stops20h 55m

Madison Truax Field

Mon 5/11

8:24 pm-1:21 pm

2 stops15h 57m

$748

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 21 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 10h 30m. There are 2204 mi between Simpson Bay and Wisconsin. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

See more FAQs

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