HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Milwaukee 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 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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$545
(Delta)

Popular in

June

Cheapest in

September

Average price

$721
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. 21% potential increase in price ($220 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 17% potential price decrease ($118 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

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 March 28, 2025.

This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 5/65:45 amMKE - SXM
1 stop7h 20mDelta
Thu 5/223:19 pmSXM - MKE
1 stop9h 35mDelta
Deal found 3/27$545
This American Airlines deal was found by Cheapflights users on 3/27. 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 5/66:38 pmMKE - SXM
2 stops18h 46mAmerican Airlines
Thu 5/222:05 pmSXM - MKE
1 stop10h 53mAmerican Airlines
Deal found 3/27$571
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/102:20 pmMKE - SXM
2 stops22h 40mMultiple Airlines
Mon 7/282:56 pmSXM - MKE
2 stops30h 00mMultiple Airlines
Deal found 3/27$643
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/105:00 pmMKE - SXM
1 stop20h 00mSpirit Airlines
Mon 7/282:56 pmSXM - MKE
2 stops30h 00mSpirit Airlines
Deal found 3/27$649

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 March 28, 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

Tue 5/6

5:45 am-2:05 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Thu 5/22

3:19 pm-11:54 pm

1 stop9h 35m

$545

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 5/6

6:38 pm-2:24 pm

2 stops18h 46m

Simpson Bay Princess Juliana

Thu 5/22

2:05 pm-11:58 pm

1 stop10h 53m

$571

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 4/10

2:20 pm-2:00 pm

2 stops22h 40m

Simpson Bay Princess Juliana

Mon 7/28

2:56 pm-7:56 pm

2 stops30h 00m

$643

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 4/10

5:00 pm-2:00 pm

1 stop20h 00m

Simpson Bay Princess Juliana

Mon 7/28

2:56 pm-7:56 pm

2 stops30h 00m

$649

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star

*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, 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 July is currently the most expensive (average of $679). 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 March 28, 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 March 28, 2025.
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Spirit Airlines
6.3
Okay
7,881 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    Delta, at $545, was found to be the cheapest airline from Milwaukee to Simpson Bay.Alternate airlines to your destination round-trip include American Airlines and Spirit 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 July is currently the most expensive (average of $679). 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 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
Madison to Simpson Bay flights
Appleton to Simpson Bay flights
Eau Claire to Simpson Bay flights
Green Bay 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$469Average$678FlexibilityNo cancel feeOn-time71%
DeltaCheapest$469Average$685FlexibilityNo 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.