Which layover airport has the shortest travel time from Milwaukee to Simpson Bay?

Flights connecting via Chicago (ORD) have the shortest average one-way travel time: 7h 27m.

Which layover airport offers the lowest fares from Milwaukee to Simpson Bay?

Flights via Chicago (ORD) offer the lowest average round-trip price of $521.

What airlines fly to Simpson Bay?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Simpson Bay from Milwaukee according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 6 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

Which airport is the most popular layover for flights between Milwaukee and Simpson Bay?

Atlanta (ATL) was the most common stop: 76% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Milwaukee to Simpson Bay?

Orlando (MCO) has the shortest average layover time for this route: 1h 50m.

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?

Prices for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport refresh daily.

How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?

There are 4 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of September 2026.

How old do you have to be to fly from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$496 Cheap Flights from Milwaukee to Simpson Bay in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Milwaukee to Simpson Bay

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5:00 am - 4:33 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

9h 33m2 stops Chicago O'Hare Intl Miami

3:20 pm - 10:48 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 28m1 stop Charlotte Douglas

$496American Airlines

Wed, Feb 24 - Wed, Mar 3

5:00 am - 4:33 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

9h 33m2 stops Chicago O'Hare Intl Miami

5:33 pm - 8:07 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

16h 34m2 stops Miami Chicago O'Hare Intl

$496American Airlines

Wed, Feb 24 - Wed, Mar 3

5:00 am - 2:05 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

8h 05m1 stop Orlando

4:40 pm - 11:35 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 55m1 stop Baltimore/Washington

$519Southwest

Fri, Oct 30 - Fri, Nov 6

5:00 am - 2:05 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

8h 05m1 stop Orlando

3:15 pm - 11:55 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 40m2 stops Orlando Nashville Intl

$524Southwest

Fri, Oct 30 - Fri, Nov 6

5:55 am - 2:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

6h 45m1 stop Atlanta Hartsfield-Jackson

5:25 pm - 11:49 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 24m1 stop Atlanta Hartsfield-Jackson

$526Delta

Tue, Jan 19 - Sat, Jan 23

6:40 pm - 2:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

18h 00m1 stop Atlanta Hartsfield-Jackson

1:40 pm - 11:49 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

12h 09m1 stop Atlanta Hartsfield-Jackson

$526Delta

Tue, Feb 2 - Fri, Feb 5

3:42 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 08m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

2:10 pm - 11:11 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

11h 01m1 stop Chicago O'Hare Intl

$526United Airlines

Sat, Jan 30 - Sat, Feb 6

6:00 am - 3:57 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 57m1 stop Chicago O'Hare Intl

2:10 pm - 7:11 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

19h 01m1 stop Chicago O'Hare Intl

$526United Airlines

Sat, Jan 30 - Sat, Feb 6

12:10 pm - 12:26 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

22h 16m2 stops Charlotte Douglas Miami

1:01 pm - 11:14 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

12h 13m1 stop Miami

$559American Airlines

Sat, Jan 30 - Mon, Feb 8

5:00 pm - 12:30 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 30m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

4:20 pm - 8:45 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 25m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County

$2,808WestJet

Fri, Jan 22 - Fri, Jan 29

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Southwest flights from Milwaukee to Simpson Bay

Our best Southwest deals on Milwaukee to Simpson Bay flight tickets

Southwest

Oct 30

MKE5:00 amMilwaukee-Mitchell

8h 05m

1 stop

SXM2:05 pmSimpson Bay Princess Juliana

Nov 6

SXM4:40 pmSimpson Bay Princess Juliana

8h 55m

1 stop

MKE11:35 pmMilwaukee-Mitchell

$519

Southwest

Oct 30

MKE5:00 amMilwaukee-Mitchell

8h 05m

1 stop

SXM2:05 pmSimpson Bay Princess Juliana

Nov 6

SXM3:15 pmSimpson Bay Princess Juliana

10h 40m

2 stops

MKE11:55 pmMilwaukee-Mitchell

$524

Southwest

Feb 21

MKE6:30 pmMilwaukee-Mitchell

18h 05m

2 stops

SXM2:35 pmSimpson Bay Princess Juliana

Feb 26

SXM2:55 pmSimpson Bay Princess Juliana

10h 25m

1 stop

MKE11:20 pmMilwaukee-Mitchell

$549

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Delta

Jan 23

MKE6:40 pmMilwaukee-Mitchell

18h 00m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

Jan 29

SXM1:40 pmSimpson Bay Princess Juliana

12h 09m

1 stop

MKE11:49 pmMilwaukee-Mitchell

$526

Delta

Jan 23

MKE3:15 pmMilwaukee-Mitchell

19h 00m

2 stops

SXM12:15 pmSimpson Bay Princess Juliana

Jan 29

SXM1:40 pmSimpson Bay Princess Juliana

12h 09m

1 stop

MKE11:49 pmMilwaukee-Mitchell

$531

Delta

Feb 21

MKE5:55 pmMilwaukee-Mitchell

16h 20m

1 stop

SXM12:15 pmSimpson Bay Princess Juliana

Mar 5

SXM4:05 pmSimpson Bay Princess Juliana

31h 32m

2 stops

MKE9:37 pmMilwaukee-Mitchell

$572

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Wed 2/24

5:00 am-4:33 pm

2 stops9h 33m

Simpson Bay Princess Juliana

Wed 3/3

3:20 pm-10:48 pm

1 stop9h 28m

$496

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Wed 2/24

5:00 am-4:33 pm

2 stops9h 33m

Simpson Bay Princess Juliana

Wed 3/3

5:33 pm-8:07 am

2 stops16h 34m

$496

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 10/30

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 11/6

4:40 pm-11:35 pm

1 stop8h 55m

$519

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 10/30

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 11/6

3:15 pm-11:55 pm

2 stops10h 40m

$524

Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/19

5:55 am-2:40 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Sat 1/23

5:25 pm-11:49 pm

1 stop8h 24m

$526

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 2/2

6:40 pm-2:40 pm

1 stop18h 00m

Simpson Bay Princess Juliana

Fri 2/5

1:40 pm-11:49 pm

1 stop12h 09m

$526

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

3:42 pm-1:50 pm

2 stops20h 08m

Simpson Bay Princess Juliana

Sat 2/6

2:10 pm-11:11 pm

1 stop11h 01m

$526

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

6:00 am-3:57 pm

1 stop7h 57m

Simpson Bay Princess Juliana

Sat 2/6

2:10 pm-7:11 am

1 stop19h 01m

$526

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

12:10 pm-12:26 pm

2 stops22h 16m

Simpson Bay Princess Juliana

Mon 2/8

1:01 pm-11:14 pm

1 stop12h 13m

$559

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 1/22

5:00 pm-12:30 pm

2 stops17h 30m

Simpson Bay Princess Juliana

Fri 1/29

4:20 pm-8:45 am

2 stops18h 25m

$2,808

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

How to get the cheapest flight ticket from Milwaukee to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

What is the typical price of a round-trip flight between Milwaukee and Simpson Bay?

Prices are currently low for flights on this route.

Typical prices usually range from $693 to $797.
The lowest price recently found on this route was $496.

What is the cheapest month to fly to Simpson Bay?

In general, July is the cheapest month to fly from Milwaukee to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you aren’t able to travel to Simpson Bay during the month of July, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $0.

When to book flights from Milwaukee to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Milwaukee to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Milwaukee to Simpson Bay (MKE to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milwaukee to Simpson Bay

Best Price Found	$496
Fastest flight time	7h 00m
Direct flights	None

The best flight deal from Milwaukee to Simpson Bay found on momondo in the last 72 hours is $496

The fastest flight from Milwaukee to Simpson Bay takes 7h 00m

There are no direct flights from Milwaukee to Simpson Bay. There are no popular flight routes from Milwaukee to Simpson Bay.

Search flight deals

Frequently asked questions about flying from Milwaukee to Simpson Bay

How far is Milwaukee-Mitchell to Simpson Bay Princess Juliana by plane?
The straight-line distance from Milwaukee-Mitchell to Simpson Bay Princess Juliana is 2252.3 mi. A reasonable flight in good conditions will take 7h 00m.
When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport refresh daily.
How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?
There are 4 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of September 2026.
How old do you have to be to fly from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Milwaukee to Simpson Bay?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Milwaukee to Simpson Bay is Delta (32% of total bookings). The next most popular airlines are American Airlines (31%), Southwest (19%), and United Airlines (18%).

Best airlines flying from Milwaukee to Simpson Bay

Compare and see reviews for airlines that fly from Milwaukee to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $478	Free Cancellation	Rating 7.4 10,220 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,590 reviews	Search Delta flights
Southwest	PriceFrom $526	Free Cancellation	Rating 8.0 4,193 reviews	Search Southwest flights
American Airlines	PriceFrom $612	Free Cancellation	Rating 7.0 12,072 reviews	Search American Airlines flights

Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Milwaukee to Simpson Bay?

Finding the right flight to Simpson Bay from Milwaukee is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Simpson Bay quick and easy, saving you time and money.

Can I find flights from Milwaukee to Simpson Bay with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Milwaukee to Simpson Bay flights to just show those with flexible booking policies.

How can momondo help me find flights from Milwaukee to Simpson Bay?

Once all potential Milwaukee to Simpson Bay flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Milwaukee to Simpson Bay right now. Can momondo alert me if prices change?

Price alerts on flights to Simpson Bay from Milwaukee are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Simpson Bay trip

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Cheap flights from Milwaukee to Simpson Bay from $496

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to Simpson Bay departing on 2/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Southwest flights from Milwaukee to Simpson Bay

Our best Southwest deals on Milwaukee to Simpson Bay flight tickets

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

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How to get the cheapest flight ticket from Milwaukee to Simpson Bay

What is the typical price of a round-trip flight between Milwaukee and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

What airlines fly to Simpson Bay?

Which airport is the most popular layover for flights between Milwaukee and Simpson Bay?

Which layover airport offers the lowest fares from Milwaukee to Simpson Bay?

Which layover airport has the shortest travel time from Milwaukee to Simpson Bay?

Which layover airport has the shortest connection time from Milwaukee to Simpson Bay?

When to book flights from Milwaukee to Simpson Bay

Cheap Milwaukee to Simpson Bay (MKE to SXM) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Milwaukee to Simpson Bay

Best airlines flying from Milwaukee to Simpson Bay

Compare and see reviews for airlines that fly from Milwaukee to Simpson Bay with momondo

Traveling to a place near Simpson Bay?

Why use momondo?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Simpson Bay

List of cabin classes available on flights landing in Simpson Bay. Availability may vary depending on flight origin and airline.

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According to popular flight searches on momondo this year