HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$232+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$497
(Delta)

One-way from

$232
(FlightHub)

Popular in

June

Cheapest in

May

Average price

$767
From Milwaukee-Mitchell to Simpson Bay Princess Juliana
Search Deals
One-way flight from Milwaukee-Mitchell to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($264 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($117 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 31, 2025.

This Delta deal was found by Cheapflights users on 7/31. 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 9/145:40 amMKE - SXM
1 stop7h 10mDelta
Sun 9/213:20 pmSXM - MKE
1 stop9h 28mDelta
Deal found 7/31$497
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 10/292:05 pmMKE - SXM
2 stops22h 32mAmerican Airlines
Wed 11/53:20 pmSXM - MKE
2 stops18h 40mAmerican Airlines
Deal found 7/30$617
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 11/12:45 pmMKE - SXM
1 stop24h 12mUnited Airlines
Sat 11/82:51 pmSXM - MKE
1 stop28h 26mUnited Airlines
Deal found 7/31$619
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:08 pmMKE - SXM
3 stops36h 42mMultiple Airlines
Sat 12/65:00 pmSXM - MKE
2 stops24h 08mMultiple Airlines
Deal found 7/30$1,698

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 July 31, 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

Sun 9/14

5:40 am-1:50 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Sun 9/21

3:20 pm-11:48 pm

1 stop9h 28m

$497

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 10/29

2:05 pm-1:37 pm

2 stops22h 32m

Simpson Bay Princess Juliana

Wed 11/5

3:20 pm-8:00 am

2 stops18h 40m

$617

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 11/1

2:45 pm-3:57 pm

1 stop24h 12m

Simpson Bay Princess Juliana

Sat 11/8

2:51 pm-5:17 pm

1 stop28h 26m

$619

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 11/29

8:08 pm-10:50 am

3 stops36h 42m

Simpson Bay Princess Juliana

Sat 12/6

5:00 pm-3:08 pm

2 stops24h 08m

$1,698

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 1/9

12:54 pm-3:10 pm

2 stops24h 16m

$232

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 1/9

5:45 am-2:56 pm

1 stop7h 11m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 $655). 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 July 31, 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 July 31, 2025.
See what other customers who have flown with Delta, United Airlines, 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
7,981 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

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
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

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
7,981 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

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!
Spirit Airlines
6.3
Okay
8,048 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

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.

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

    Delta, at $497, was found to be the cheapest airline from Milwaukee to Simpson Bay.Alternate airlines to your destination round-trip include American Airlines and United Airlines. You may be able to fly from Milwaukee to Simpson Bay for 39% 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 $655). 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
Green Bay to Simpson Bay flights
Appleton 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$504Average$717FlexibilityNo cancel feeOn-time71%
DeltaCheapest$514Average$684FlexibilityNo 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.