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Simpson Bay

$527+ Cheap flights from Milwaukee (MKE) to Simpson Bay (SXM)

This is the cheapest round-trip 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
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Milwaukee to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$527
(United Airlines)

Popular in

June

Cheapest in

September

Average price

$612
From Milwaukee-Mitchell to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($280 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease ($114 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Milwaukee to Simpson Bay

Cheapest flights from Milwaukee to Simpson Bay
Explore the most affordable flight options available from Milwaukee to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:39 pmMKE - SXM
1 stop19h 18mUnited Airlines
Tue 11/42:52 pmSXM - MKE
2 stops22h 37mUnited Airlines
Deal found 9/14$527
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 10/308:16 pmMKE - SXM
2 stops17h 59mAmerican Airlines
Thu 11/65:24 pmSXM - MKE
2 stops16h 58mAmerican Airlines
Deal found 9/15$636
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:20 pmMKE - SXM
2 stops24h 17mAmerican Airlines
Tue 11/45:24 pmSXM - MKE
2 stops20h 37mAmerican Airlines
Deal found 9/14$657
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/217:13 pmMKE - SXM
2 stops18h 58mAmerican Airlines
Mon 11/242:51 pmSXM - MKE
1 stop10h 05mAmerican Airlines
Deal found 9/14$820
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:30 amMKE - SXM
2 stops27h 20mUnited Airlines
Tue 12/304:55 pmSXM - MKE
2 stops27h 58mUnited Airlines
Deal found 9/15$837
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/223:48 pmMKE - SXM
2 stops20h 02mUnited Airlines
Wed 12/314:55 pmSXM - MKE
2 stops20h 32mUnited Airlines
Deal found 9/15$916
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:40 amMKE - SXM
1 stop7h 10mDelta
Mon 12/291:50 pmSXM - MKE
1 stop8h 08mDelta
Deal found 9/15$923
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:36 amMKE - SXM
2 stops29h 14mUnited Airlines
Mon 12/294:55 pmSXM - MKE
2 stops20h 32mUnited Airlines
Deal found 9/15$925
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/203:47 pmMKE - SXM
2 stops20h 32mAmerican Airlines
Sat 9/272:20 pmSXM - MKE
2 stops20h 44mAmerican Airlines
Deal found 9/14$957
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:40 amMKE - SXM
1 stop7h 10mDelta
Wed 12/311:50 pmSXM - MKE
1 stop10h 54mDelta
Deal found 9/15$967

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 September 15, 2025.
Use the filters below to find and compare flights from Milwaukee to Simpson Bay that are best for you.

Fly from

Milwaukee

Fly to

Simpson Bay

Route

Depart

Return

Price

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 10/31

6:39 pm-2:57 pm

1 stop19h 18m

Simpson Bay Princess Juliana

Tue 11/4

2:52 pm-11:29 am

2 stops22h 37m

$527

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 10/30

8:16 pm-3:15 pm

2 stops17h 59m

Simpson Bay Princess Juliana

Thu 11/6

5:24 pm-8:22 am

2 stops16h 58m

$636

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 10/31

12:20 pm-1:37 pm

2 stops24h 17m

Simpson Bay Princess Juliana

Tue 11/4

5:24 pm-12:01 pm

2 stops20h 37m

$657

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 11/21

7:13 pm-4:11 pm

2 stops18h 58m

Simpson Bay Princess Juliana

Mon 11/24

5:24 pm-12:01 pm

2 stops20h 37m

$820

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 12/22

8:30 am-1:50 pm

2 stops27h 20m

Simpson Bay Princess Juliana

Tue 12/30

4:55 pm-6:53 pm

2 stops27h 58m

$837

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 12/22

3:48 pm-1:50 pm

2 stops20h 02m

Simpson Bay Princess Juliana

Mon 12/29

4:55 pm-11:27 am

2 stops20h 32m

$837

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 12/22

5:40 am-2:50 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Mon 12/29

1:50 pm-7:58 pm

1 stop8h 08m

$923

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 12/24

6:36 am-1:50 pm

2 stops29h 14m

Simpson Bay Princess Juliana

Mon 12/29

4:55 pm-11:27 am

2 stops20h 32m

$925

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Best time to book a flight from Milwaukee to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Milwaukee 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 Milwaukee to Simpson Bay

What is the cheapest month to book a flight from Milwaukee to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Milwaukee to Simpson Bay (average of $459). Flying from Milwaukee to Simpson Bay in March is currently the most expensive (average of $652). 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 MKE to SXM?

Find hourly flight availability from Milwaukee 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 September 15, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 9% on flights from Milwaukee to Simpson Bay by exploring options for tickets at noon.

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 September 15, 2025.
See what other customers who have flown with Delta and American Airlines from Milwaukee to Simpson Bay have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

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
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

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
7,954 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

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 Milwaukee to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    United Airlines and American Airlines can get you from Milwaukee to Simpson Bay in just under 17h 59m. Your travel time can differ by up to 1h 19m. There are 2248 mi between Milwaukee and Simpson Bay. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Milwaukee to Simpson Bay round-trip?

    Delta, at $572, was found to be the cheapest airline from Milwaukee to Simpson Bay. An alternate airline flying to your destination would be American Airlines. You may be able to fly from Milwaukee to Simpson Bay for 32% less than the average price by searching for these airlines.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Milwaukee to Simpson Bay (average of $459). Flying from Milwaukee to Simpson Bay in March is currently the most expensive (average of $652). 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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Alternative routes for Milwaukee to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Simpson Bay flights
Minneapolis to Simpson Bay flights
Appleton to Simpson Bay flights
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Madison to Simpson Bay flights
Eau Claire to Simpson Bay flights

Top 2 airlines flying from Milwaukee to Simpson Bay

Discover the top 2 airlines that operate flights from Milwaukee 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$572Average$696FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$584Average$750FlexibilityNo cancel feeOn-time71%

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