$211 Cheap Flights from Milwaukee (MKE) to Philipsburg (SXM)

View $211 flight on Thu, Feb 19, 2026Opens in a new window

Popular airlines from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM)

Cheap Flights from Milwaukee to Philipsburg (MKE-SXM)

Prices were available within the past 7 days and start at $211 for one-way flights and $517 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Oct 27 - Wed, Nov 12
MKE
Milwaukee
SXM
Saint Martin
$517 Roundtrip, found 4 hours ago
$517
Roundtrip
found 4 hours ago
Select Delta flight, departing Mon, Oct 27 from Milwaukee to Saint Martin, returning Wed, Nov 12, priced at $517 found 4 hours ago
Delta
Sun, Oct 19 - Sun, Oct 26
MKE
Milwaukee
SXM
Saint Martin
$524 Roundtrip, found 5 days ago
$524
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Oct 19 from Milwaukee to Saint Martin, returning Sun, Oct 26, priced at $524 found 5 days ago
United
Fri, Oct 31 - Fri, Nov 7
MKE
Milwaukee
SXM
Saint Martin
$530 Roundtrip, found 8 hours ago
$530
Roundtrip
found 8 hours ago
Select United flight, departing Fri, Oct 31 from Milwaukee to Saint Martin, returning Fri, Nov 7, priced at $530 found 8 hours ago
United
Sat, Nov 8 - Wed, Nov 12
MKE
Milwaukee
SXM
Saint Martin
$536 Roundtrip, found 6 hours ago
$536
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Nov 8 from Milwaukee to Saint Martin, returning Wed, Nov 12, priced at $536 found 6 hours ago
Delta
Mon, Oct 6 - Mon, Oct 13
MKE
Milwaukee
SXM
Saint Martin
$537 Roundtrip, found 5 days ago
$537
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Oct 6 from Milwaukee to Saint Martin, returning Mon, Oct 13, priced at $537 found 5 days ago
JetBlue Airways
Sat, Oct 18 - Wed, Oct 22
MKE
Milwaukee
SXM
Saint Martin
$547 Roundtrip, found 6 days ago
$547
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Oct 18 from Milwaukee to Saint Martin, returning Wed, Oct 22, priced at $547 found 6 days ago
United
Sat, Nov 8 - Wed, Nov 12
MKE
Milwaukee
SXM
Saint Martin
$557 Roundtrip, found 6 hours ago
$557
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Nov 8 from Milwaukee to Saint Martin, returning Wed, Nov 12, priced at $557 found 6 hours ago
Delta
Mon, Oct 6 - Wed, Oct 8
MKE
Milwaukee
SXM
Saint Martin
$557 Roundtrip, found 5 days ago
$557
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Oct 6 from Milwaukee to Saint Martin, returning Wed, Oct 8, priced at $557 found 5 days ago
American Airlines
Sat, Nov 8 - Wed, Nov 12
MKE
Milwaukee
SXM
Saint Martin
$587 Roundtrip, found 6 hours ago
$587
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Nov 8 from Milwaukee to Saint Martin, returning Wed, Nov 12, priced at $587 found 6 hours ago
Spirit Airlines
Thu, Feb 19 - Sat, Feb 28
MKE
Milwaukee
SXM
Saint Martin
$610 Roundtrip, found 7 hours ago
$610
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Thu, Feb 19 from Milwaukee to Saint Martin, returning Sat, Feb 28, priced at $610 found 7 hours ago

Find the cheapest month to fly from Milwaukee (MKE) to Simpson Bay (SXM)

December is typically the cheapest month to fly

From $390 - $1,556 per traveler.

Alternative airports near Simpson Bay

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Clayton J. Lloyd Intl. AXA. Flights from $1,454
AXA
Clayton J. Lloyd Intl.
Flights from $1,454
Select flight to Gustaf III SBH. Flights from $1,132
SBH
Gustaf III
Flights from $1,132

Frequently asked questions

How much does a flight from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM) cost?
Secure a cheap one-way flight from $211 or cheap return flight from $517 from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM)?
October is the cheapest month to fly from MKE to SXM. Traveling during quieter months is often the key to scoring lower fares.
What is the cheapest airline that flies from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM)?
To find the cheapest airline that'll fly you from MKE to SXM, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM)?
There are no daily nonstop flights available from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM). But you can opt for flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from MKE to SXM?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM)?
To avoid possible delays on the General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM) route, aim to travel before 3 PM. Later flights have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM) last-minute?
Last-minute bookings from MKE to SXM are generally more expensive. To secure the lowest rates, start searching for flights well ahead of time. That being said, if you're flexible with your travel plans, it's possible to score a cheap ticket just before your departure.
Is it cheaper to book a MKE to SXM flight and hotel package?
Securing a MKE to SXM flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our extensive range of accommodations and then add flights, car rentals and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from General Mitchell Intl. Airport (MKE) to Princess Juliana Intl. Airport (SXM)?
If you reserved your MKE to SXM flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

Travel information

Travel information

Origin airport
General Mitchell Intl.
Destination airport
Princess Juliana Intl.
Airlines serving
Air Canada, American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$517
Distance
2249 mi

Book with confidence

Book with confidence

Milwaukee to Philipsburg Flights

The cheapest times to fly from Milwaukee to Philipsburg

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Milwaukee to Philipsburg are during the month of October. You can find some of the cheapest flights from Milwaukee to Philipsburg with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Milwaukee to Philipsburg

Sunday is one of the best days to book for cheap flights from Milwaukee to Philipsburg: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Milwaukee to Philipsburg

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Milwaukee to Philipsburg in 2025. You can also book with separate airlines for your outbound and return journeys, from $211 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Milwaukee to Philipsburg flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Milwaukee to Philipsburg airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Milwaukee to Philipsburg Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.