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Simpson Bay

$545+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap 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 January 28, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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.
Wed 2/255:23 am
MKE
-
SXM
1 stop7h 27m
Delta
Wed 3/41:38 pm
SXM
-
MKE
1 stop8h 35m
Delta
Deal found 1/27$545
This Delta deal was found by Cheapflights users on 1/26. 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.
Sun 2/155:23 am
MKE
-
SXM
1 stop7h 27m
Delta
Sat 2/215:25 pm
SXM
-
MKE
1 stop8h 22m
Delta
Deal found 1/26$565
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 3/106:38 am
MKE
-
SXM
1 stop7h 50m
American Airlines
Fri 3/204:01 pm
SXM
-
MKE
1 stop19h 00m
American Airlines
Deal found 1/27$615
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 3/185:09 am
MKE
-
SXM
2 stops9h 19m
American Airlines
Thu 3/262:17 pm
SXM
-
MKE
2 stops20h 44m
American Airlines
Deal found 1/27$620
This American Airlines deal was found by Cheapflights users on 1/26. 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 3/2110:27 am
MKE
-
SXM
1 stop27h 33m
American Airlines
Fri 3/274:01 pm
SXM
-
MKE
1 stop19h 00m
American Airlines
Deal found 1/26$625
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 3/256:37 pm
MKE
-
SXM
1 stop17h 39m
American Airlines
Wed 4/14:01 pm
SXM
-
MKE
1 stop19h 00m
American Airlines
Deal found 1/27$640
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 3/73:11 pm
MKE
-
SXM
2 stops18h 18m
American Airlines
Sat 3/142:00 pm
SXM
-
MKE
1 stop10h 12m
American Airlines
Deal found 1/27$645
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 4/206:41 pm
MKE
-
SXM
1 stop17h 40m
American Airlines
Sat 4/253:32 pm
SXM
-
MKE
1 stop8h 15m
American Airlines
Deal found 1/27$658

Find 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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$545
(Delta)

Popular in

June

Cheapest in

August

Average price

$695
Provider with most accurate pricing for Milwaukee-Mitchell-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Simpson Bay Princess Juliana flights.
Search Deals
From Milwaukee-Mitchell to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($285 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($101 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 28, 2026.
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

Wed 2/25

5:23 am-2:50 pm

1 stop7h 27m

Simpson Bay Princess Juliana

Wed 3/4

1:38 pm-8:13 pm

1 stop8h 35m

$545

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/15

5:23 am-2:50 pm

1 stop7h 27m

Simpson Bay Princess Juliana

Sat 2/21

5:25 pm-11:47 pm

1 stop8h 22m

$565

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 6/9

5:51 pm-12:45 pm

1 stop17h 54m

Simpson Bay Princess Juliana

Wed 6/24

2:45 pm-11:59 pm

1 stop10h 14m

$615

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 3/10

6:38 am-3:28 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Fri 3/20

4:01 pm-10:01 am

1 stop19h 00m

$615

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 3/18

6:38 am-3:28 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Thu 3/26

2:21 pm-11:45 pm

1 stop10h 24m

$615

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 3/25

5:10 am-3:28 pm

2 stops9h 18m

Simpson Bay Princess Juliana

Wed 4/1

4:01 pm-10:01 am

1 stop19h 00m

$620

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Simpson Bay flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, February is the cheapest month in which you can book a flight from Milwaukee to Simpson Bay (average of $241). 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.

How much does it cost to fly round-trip from Milwaukee to Simpson Bay?

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 January 28, 2026.
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
8,123 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,123 reviews
Delta
7.9
Good
8,123 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,201 reviews
Delta
7.9
Good
8,123 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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?

    Delta and American Airlines can get you from Milwaukee to Simpson Bay in just under 7h 27m. Your travel time can differ by up to 10h 27m. 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?

    American Airlines, at $605, was found to be the cheapest airline from Milwaukee to Simpson Bay. An alternate airline flying to your destination would be Delta. 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, February is the cheapest month in which you can book a flight from Milwaukee to Simpson Bay (average of $241). 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
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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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$605Average$734FlexibilityNo cancel feeOn-time71%
DeltaCheapest$612Average$743FlexibilityNo cancel feeOn-timeN/A

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