HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$158+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$313
(Priceline)

One-way from

$158
(SmartFares)

Popular in

June

Cheapest in

May

Average price

$1,991
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. 23% potential increase in price ($253 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($118 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 12, 2025.

This Priceline deal was found by Cheapflights users on 6/11. 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.
Fri 9/56:10 amORD - SXM
1 stop29h 15mFrontier
Sat 9/131:58 pmSXM - ORD
1 stop23h 59mFrontier
Deal found 6/11$313
This Booking.com deal was found by Cheapflights users on 6/10. 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 stop8h 19mMultiple Airlines
Sat 9/131:58 pmSXM - ORD
1 stop23h 59mMultiple Airlines
Deal found 6/10$366
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 7/165:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 7/263:05 pmSXM - ORD
1 stop9h 48mSpirit Airlines
Deal found 6/10$377
This FlightHub deal was found by Cheapflights users on 6/12. 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.
Tue 9/92:22 pmMSP - SXM
2 stops23h 02mSpirit Airlines
Sat 9/203:27 pmSXM - MSP
2 stops22h 50mSpirit Airlines
Deal found 6/12$447
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/313:48 pmMSP - SXM
3 stops21h 12mMultiple Airlines
Wed 8/63:05 pmSXM - MSP
2 stops22h 11mMultiple Airlines
Deal found 6/10$525
This FlightHub deal was found by Cheapflights users on 6/11. 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.
Thu 12/48:25 pmORD - SXM
1 stop17h 50mAir Canada
Sat 12/135:15 pmSXM - ORD
1 stop19h 43mAir Canada
Deal found 6/11$530
This FlightHub deal was found by Cheapflights users on 6/12. 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.
Sun 8/34:37 pmMKE - SXM
2 stops20h 23mSpirit Airlines
Fri 8/83:05 pmSXM - MKE
2 stops49h 37mSpirit Airlines
Deal found 6/12$571
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 7/95:35 amORD - SXM
1 stop7h 21mDelta
Tue 7/153:21 pmSXM - ORD
1 stop9h 48mDelta
Deal found 6/10$587
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Mon 10/205:19 pmMKE - SXM
2 stops18h 56mAmerican Airlines
Fri 10/244:10 pmSXM - MKE
2 stops20h 34mAmerican Airlines
Deal found 6/10$610
This American Airlines deal was found by Cheapflights users on 6/11. 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 10/186:55 pmORD - SXM
1 stop17h 20mAmerican Airlines
Sat 10/252:40 pmSXM - ORD
1 stop8h 54mAmerican Airlines
Deal found 6/11$612
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/132:01 pmMSN - SXM
2 stops22h 18mAmerican Airlines
Sat 9/202:35 pmSXM - MSN
1 stop9h 35mAmerican Airlines
Deal found 6/11$617
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 9/136:00 amMKE - SXM
1 stop6h 50mDelta
Sat 9/203:15 pmSXM - MKE
1 stop9h 10mDelta
Deal found 6/11$637

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 June 12, 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

Fri 9/5

6:10 am-12:25 pm

1 stop29h 15m

Simpson Bay Princess Juliana

Sat 9/13

1:58 pm-12:57 pm

1 stop23h 59m

$313

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:24 pm

1 stop8h 19m

Simpson Bay Princess Juliana

Sat 9/13

1:58 pm-12:57 pm

1 stop23h 59m

$366

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 7/16

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 7/26

3:05 pm-11:53 pm

1 stop9h 48m

$377

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Tue 9/9

2:22 pm-2:24 pm

2 stops23h 02m

Simpson Bay Princess Juliana

Sat 9/20

3:27 pm-1:17 pm

2 stops22h 50m

$447

MinneapolisSimpson Bay

MSP - SXM

MSPSXM

Minneapolis St Paul

Thu 7/31

3:48 pm-2:00 pm

3 stops21h 12m

Simpson Bay Princess Juliana

Wed 8/6

3:05 pm-12:16 pm

2 stops22h 11m

$525

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/4

8:25 pm-4:15 pm

1 stop17h 50m

Simpson Bay Princess Juliana

Sat 12/13

5:15 pm-10:58 am

1 stop19h 43m

$530

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 8/3

4:37 pm-2:00 pm

2 stops20h 23m

Simpson Bay Princess Juliana

Fri 8/8

3:05 pm-3:42 pm

2 stops49h 37m

$571

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 7/9

5:35 am-1:56 pm

1 stop7h 21m

Simpson Bay Princess Juliana

Tue 7/15

3:21 pm-12:09 am

1 stop9h 48m

$587

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 10/20

5:19 pm-1:15 pm

2 stops18h 56m

Simpson Bay Princess Juliana

Fri 10/24

4:10 pm-11:44 am

2 stops20h 34m

$610

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

6:55 pm-1:15 pm

1 stop17h 20m

Simpson Bay Princess Juliana

Sat 10/25

2:40 pm-10:34 pm

1 stop8h 54m

$612

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 37 results
1
2
3
4

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 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 June 12, 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 June 12, 2025.
Peruse reviews from past customers who have flown with Delta, Copa Airlines and United Airlines from Wisconsin to Simpson Bay to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

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!
Copa Airlines
7.5
Good
1,451 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

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
7,950 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

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
2,868 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

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 $158. However, be on the lookout for offers from Frontier and WestJet, 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 $657). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Simpson Bay flights
Newark to Simpson Bay flights
LaGuardia to Simpson Bay flights
Dulles Intl to Simpson Bay flights
Atlanta to Simpson Bay flights
Boston to Simpson Bay flights
Baltimore to Simpson Bay flights
Reagan-National to Simpson Bay flights
Miami to Simpson Bay flights
Philadelphia to Simpson Bay flights
O'Hare Intl to Simpson Bay flights
Charlotte to Simpson Bay flights
Los Angeles to Simpson Bay flights
Dallas/Fort Worth to Simpson Bay flights
Fort Lauderdale to Simpson Bay flights
Orlando to Simpson Bay flights
Tampa to Simpson Bay flights
Richmond to Simpson Bay flights
Hobby to Simpson Bay flights
San Francisco to Simpson Bay flights
Denver to Simpson Bay flights
Raleigh to Simpson Bay flights
George Bush Intcntl to Simpson Bay flights
New Orleans to Simpson Bay flights
Seattle to Simpson Bay flights
Nashville to Simpson Bay flights
Hartford to Simpson Bay flights
Minneapolis to Simpson Bay flights
Austin to Simpson Bay flights
Detroit to Simpson Bay flights
Charleston to Simpson Bay flights
Ontario to Simpson Bay flights
White Plains to Simpson Bay flights
Omaha to Simpson Bay flights
Pittsburgh to Simpson Bay flights
Sky Harbor Intl to Simpson Bay flights
Roanoke to Simpson Bay flights
St. Louis to Simpson Bay flights
Cincinnati to Simpson Bay flights
Memphis to Simpson Bay flights
West Palm Beach to Simpson Bay flights
San Antonio to Simpson Bay flights
Salt Lake City to Simpson Bay flights
Columbus to Simpson Bay flights
Cleveland to Simpson Bay flights
Norfolk to Simpson Bay flights
Jacksonville to Simpson Bay flights
Midway to Simpson Bay flights
Birmingham to Simpson Bay flights
Love Field to Simpson Bay flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$504Average$785FlexibilityNo cancel feeOn-time71%
DeltaCheapest$509Average$710FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.