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$359+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MKE
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$443
(Frontier)

One-way from

$359
(Kiwi.com)
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 April 24, 2025.

This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/712:33 pmSXM - ORD
1 stop12h 33mFrontier
Sat 6/145:01 amORD - SXM
2 stops11h 15mFrontier
Deal found 4/23$443
This Booking.com deal was found by Cheapflights users on 4/23. 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 6/712:33 pmSXM - ORD
1 stop12h 33mMultiple Airlines
Sat 6/145:05 amORD - SXM
1 stop7h 55mMultiple Airlines
Deal found 4/23$474
This Mytrip deal was found by Cheapflights users on 4/23. 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 6/73:05 pmSXM - ORD
2 stops19h 19mSpirit Airlines
Sat 6/149:28 pmORD - SXM
3 stops39h 32mSpirit Airlines
Deal found 4/23$553
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Tue 8/2612:15 pmSXM - ORD
1 stop12h 10mJetBlue
Sat 8/306:00 amORD - SXM
1 stop7h 41mJetBlue
Deal found 4/23$575
This American Airlines deal was found by Cheapflights users on 4/23. 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 10/94:10 pmSXM - ORD
1 stop8h 47mAmerican Airlines
Wed 10/156:00 amORD - SXM
1 stop8h 10mAmerican Airlines
Deal found 4/23$618
This WestJet deal was found by Cheapflights users on 4/23. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/92:10 pmSXM - ORD
2 stops27h 33mWestJet
Wed 10/151:16 pmORD - SXM
2 stops23h 03mWestJet
Deal found 4/23$1,335
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 10/911:55 amSXM - ORD
3 stops31h 55mUnited Airlines
Wed 10/152:20 pmORD - SXM
2 stops20h 00mUnited Airlines
Deal found 4/23$8,127

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 April 24, 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 6/7

12:33 pm-12:06 am

1 stop12h 33m

Chicago O'Hare Intl

Sat 6/14

5:01 am-5:16 pm

2 stops11h 15m

$443

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/7

12:33 pm-12:06 am

1 stop12h 33m

Chicago O'Hare Intl

Sat 6/14

5:05 am-2:00 pm

1 stop7h 55m

$474

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/7

3:05 pm-9:24 am

2 stops19h 19m

Chicago O'Hare Intl

Sat 6/14

9:28 pm-2:00 pm

3 stops39h 32m

$553

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 8/26

12:15 pm-11:25 pm

1 stop12h 10m

Chicago O'Hare Intl

Sat 8/30

6:00 am-2:41 pm

1 stop7h 41m

$575

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

4:10 pm-11:57 pm

1 stop8h 47m

Chicago O'Hare Intl

Wed 10/15

6:00 am-3:10 pm

1 stop8h 10m

$618

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

2:10 pm-4:43 pm

2 stops27h 33m

Chicago O'Hare Intl

Wed 10/15

1:16 pm-1:19 pm

2 stops23h 03m

$1,335

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

11:55 am-6:50 pm

3 stops31h 55m

Chicago O'Hare Intl

Wed 10/15

2:20 pm-11:20 am

2 stops20h 00m

$8,127

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 5/13

6:45 pm-5:41 pm

3 stops23h 56m

$359

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 5/13

12:40 pm-9:54 pm

1 stop10h 14m

$433

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 5/13

2:24 pm-12:11 am

2 stops10h 47m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

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

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated April 24, 2025.
United Airlines
7.4
Good
8,685 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
United Airlines
7.4
Good
8,685 reviews
United Airlines
7.4
Good
8,685 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
JetBlue
7.3
Good
2,924 reviews
United Airlines
7.4
Good
8,685 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,685 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
WestJet
7.2
Good
2,816 reviews
United Airlines
7.4
Good
8,685 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
Spirit Airlines
6.3
Okay
7,942 reviews
United Airlines
7.4
Good
8,685 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

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.

  • 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.

See more FAQs

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