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Simpson Bay

$201+ Cheap flights from Milwaukee (MKE) 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$539
(Mytrip)

One-way from

$201
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$671
Provider with most accurate pricing for Milwaukee-Mitchell-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Simpson Bay Princess Juliana flights.
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From Milwaukee-Mitchell to Simpson Bay Princess Juliana
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One-way flight from Milwaukee-Mitchell to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 24% potential increase in price ($282 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease ($115 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
sáb. 12/66:34 pmMKE - SXM
1 stop17h 24mAmerican Airlines
mié. 12/102:51 pmSXM - MKE
1 stop10h 10mAmerican Airlines
Deal found 10/28$587
This Delta deal was found by Cheapflights users on 10/28. 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.
vie. 11/285:45 amMKE - SXM
1 stop7h 10mDelta
mié. 12/33:53 pmSXM - MKE
1 stop10h 01mDelta
Deal found 10/28$612
This American Airlines deal was found by Cheapflights users on 10/30. 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.
jue. 12/116:50 pmMKE - SXM
2 stops19h 35mAmerican Airlines
mar. 12/165:25 pmSXM - MKE
2 stops23h 39mAmerican Airlines
Deal found 10/30$617
This American Airlines deal was found by Cheapflights users on 10/28. 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.
vie. 12/53:42 pmMKE - SXM
1 stop21h 26mAmerican Airlines
mié. 12/102:51 pmSXM - MKE
1 stop10h 10mAmerican Airlines
Deal found 10/28$618
This American Airlines deal was found by Cheapflights users on 10/27. 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.
sáb. 12/66:34 pmMKE - SXM
1 stop17h 24mAmerican Airlines
mar. 12/95:25 pmSXM - MKE
2 stops20h 39mAmerican Airlines
Deal found 10/27$631
This Delta deal was found by Cheapflights users on 10/28. 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.
jue. 12/115:45 amMKE - SXM
1 stop6h 43mDelta
mar. 12/163:53 pmSXM - MKE
1 stop10h 01mDelta
Deal found 10/28$651
This American Airlines deal was found by Cheapflights users on 10/27. 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.
vie. 12/53:42 pmMKE - SXM
2 stops20h 38mAmerican Airlines
mar. 12/95:25 pmSXM - MKE
2 stops24h 28mAmerican Airlines
Deal found 10/27$656
This Mytrip deal was found by Cheapflights users on 10/28. 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.
vie. 12/1210:34 amMKE - SXM
3 stops25h 41mSpirit Airlines
vie. 12/193:20 pmSXM - MKE
3 stops30h 00mSpirit Airlines
Deal found 10/28$659
This Delta deal was found by Cheapflights users on 10/27. 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.
vie. 12/55:45 amMKE - SXM
1 stop6h 43mDelta
mar. 12/93:53 pmSXM - MKE
1 stop10h 01mDelta
Deal found 10/27$770
This Delta deal was found by Cheapflights users on 10/27. 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.
sáb. 12/65:45 amMKE - SXM
1 stop7h 05mDelta
mar. 12/93:53 pmSXM - MKE
1 stop10h 01mDelta
Deal found 10/27$846

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 octubre 30, 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

sáb. 12/6

6:34 pm-1:58 pm

1 stop17h 24m

Simpson Bay Princess Juliana

mié. 12/10

2:51 pm-11:01 pm

1 stop10h 10m

$587

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

mié. 1/28

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

mié. 2/4

3:09 pm-11:23 pm

1 stop10h 14m

$587

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

mar. 3/3

12:13 pm-12:40 pm

2 stops22h 27m

Simpson Bay Princess Juliana

mar. 3/10

2:15 pm-10:25 pm

1 stop9h 10m

$592

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 11/28

5:45 am-2:55 pm

1 stop7h 10m

Simpson Bay Princess Juliana

mié. 12/3

3:53 pm-11:54 pm

1 stop10h 01m

$612

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 12/12

5:45 am-2:28 pm

1 stop6h 43m

Simpson Bay Princess Juliana

vie. 12/19

1:45 pm-8:19 pm

1 stop8h 34m

$612

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

jue. 12/11

5:45 am-2:28 pm

1 stop6h 43m

Simpson Bay Princess Juliana

mar. 12/16

3:53 pm-11:54 pm

1 stop10h 01m

$612

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

sáb. 1/3

4:57 pm-1:26 pm

1 stop18h 29m

Simpson Bay Princess Juliana

sáb. 1/10

3:23 pm-11:35 pm

1 stop10h 12m

$612

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

jue. 1/8

1:56 pm-3:10 pm

3 stops23h 14m

Simpson Bay Princess Juliana

jue. 1/15

11:30 am-11:29 am

3 stops25h 59m

$616

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 12/12

3:42 pm-12:10 pm

2 stops18h 28m

Simpson Bay Princess Juliana

vie. 12/19

3:28 pm-12:44 am

2 stops11h 16m

$617

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 11/28

6:48 pm-4:22 pm

2 stops19h 34m

Simpson Bay Princess Juliana

mié. 12/3

5:25 pm-10:44 am

2 stops19h 19m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 13 results
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Compare providers for flights from Milwaukee to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milwaukee to Simpson Bay in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Milwaukee-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Milwaukee-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Simpson Bay flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Milwaukee-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $312). Flying from Milwaukee to Simpson Bay in June is currently the most expensive (average of $595). 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 octubre 30, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 30% on flights from Milwaukee to Simpson Bay by exploring options for tickets in the afternoon.

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 octubre 30, 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
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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?

    American Airlines and Delta can get you from Milwaukee to Simpson Bay in just under 7h 10m. Your travel time can differ by up to 10h 14m. 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 $584, 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 31% 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 $312). Flying from Milwaukee to Simpson Bay in June is currently the most expensive (average of $595). 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
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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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$584Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$605Average$735FlexibilityNo cancel feeOn-time71%

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