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 has the shortest connection time from Milwaukee to Simpson Bay?

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

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.

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

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

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.

$519 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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

6:38 pm - 12:33 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

16h 55m1 stop Newark

1:35 pm - 11:37 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

11h 02m1 stop Newark

$519United Airlines

Fri, Oct 16 - Sat, Oct 24

12:05 pm - 12:33 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

23h 28m2 stops Chicago O'Hare Intl Newark

1:35 pm - 11:37 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

11h 02m1 stop Newark

$524United Airlines

Fri, Oct 16 - Sat, Oct 24

2:20 pm - 12:33 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 13m2 stops Chicago O'Hare Intl Newark

1:35 pm - 8:36 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

20h 01m2 stops Newark Chicago O'Hare Intl

$524United Airlines

Fri, Oct 16 - Sat, Oct 24

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

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

$542Southwest

Fri, Oct 30 - Fri, Nov 6

6:30 pm - 2:35 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

18h 05m2 stops Denver Intl Orlando

2:55 pm - 11:20 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 25m1 stop Orlando

$549Southwest

Sun, Feb 21 - Fri, Feb 26

5:47 pm - 3:39 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 52m2 stops Dallas/Fort Worth Miami

5:33 pm - 11:03 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

19h 30m2 stops Miami Chicago O'Hare Intl

$560American Airlines

Fri, Oct 30 - Fri, Nov 6

7:29 pm - 4:31 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 02m2 stops Chicago O'Hare Intl Miami

3:41 pm - 7:48 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 07m2 stops Charlotte Douglas Chicago O'Hare Intl

$560American Airlines

Fri, Nov 6 - Fri, Nov 13

6:40 pm - 11:30 amMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

15h 50m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

4:20 pm - 9:22 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 02m1 stop Atlanta Hartsfield-Jackson

$678Delta

Tue, Mar 23 - Sat, Apr 3

Cheap last minute flights

Enter your travel dates to find the best prices.

5:30 am - 1:53 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 23m1 stop Atlanta Hartsfield-Jackson

3:18 pm - 11:48 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 30m1 stop Atlanta Hartsfield-Jackson

$813Delta

Sun, Sep 27 - Sat, Oct 3

5:30 am - 1:53 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 23m1 stop Atlanta Hartsfield-Jackson

3:18 pm - 11:48 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 30m1 stop Atlanta Hartsfield-Jackson

$813Delta

Mon, Sep 28 - Sat, Oct 3

5:53 pm - 1:23 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

18h 30m2 stops Charlotte Douglas Miami

2:53 pm - 11:07 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 14m2 stops Charlotte Douglas Chicago O'Hare Intl

$880American Airlines

Mon, Sep 28 - Sat, Oct 3

8:14 pm - 1:23 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

16h 09m2 stops Chicago O'Hare Intl Miami

2:53 pm - 11:07 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 14m2 stops Charlotte Douglas Chicago O'Hare Intl

$880American Airlines

Sun, Sep 27 - Sat, Oct 3

5:53 pm - 1:23 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

18h 30m2 stops Philadelphia Miami

2:53 pm - 12:51 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

22h 58m1 stop Charlotte Douglas

$892American Airlines

Mon, Sep 28 - Sat, Oct 3

6:43 pm - 1:23 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 40m2 stops Charlotte Douglas Miami

2:53 pm - 12:51 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

22h 58m1 stop Charlotte Douglas

$892American Airlines

Sun, Sep 27 - Sat, Oct 3

5:10 pm - 1:23 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 13m2 stops Philadelphia Miami

2:23 pm - 11:07 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 44m2 stops Miami Chicago O'Hare Intl

$993American Airlines

Tue, Sep 29 - Sat, Oct 3

5:10 pm - 1:23 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 13m2 stops Philadelphia Miami

2:53 pm - 12:51 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

22h 58m1 stop Charlotte Douglas

$1,005American Airlines

Tue, Sep 29 - Sat, Oct 3

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Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Delta

Jan 19

MKE5:55 amMilwaukee-Mitchell

6h 45m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

Jan 23

SXM5:25 pmSimpson Bay Princess Juliana

8h 24m

1 stop

MKE11:49 pmMilwaukee-Mitchell

$526

Delta

Oct 31

MKE5:30 amMilwaukee-Mitchell

7h 10m

1 stop

SXM1:40 pmSimpson Bay Princess Juliana

Nov 7

SXM4:05 pmSimpson Bay Princess Juliana

9h 48m

1 stop

MKE11:53 pmMilwaukee-Mitchell

$684

Delta

Oct 31

MKE5:30 amMilwaukee-Mitchell

7h 10m

1 stop

SXM1:40 pmSimpson Bay Princess Juliana

Nov 7

SXM4:05 pmSimpson Bay Princess Juliana

9h 48m

1 stop

MKE11:53 pmMilwaukee-Mitchell

$707

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

SXM3:15 pmSimpson Bay Princess Juliana

10h 40m

2 stops

MKE11:55 pmMilwaukee-Mitchell

$542

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

Southwest

Jan 19

MKE3:50 pmMilwaukee-Mitchell

20h 45m

2 stops

SXM2:35 pmSimpson Bay Princess Juliana

Jan 23

SXM2:30 pmSimpson Bay Princess Juliana

9h 25m

1 stop

MKE9:55 pmMilwaukee-Mitchell

$562

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

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 10/16

6:38 pm-12:33 pm

1 stop16h 55m

Simpson Bay Princess Juliana

Sat 10/24

1:35 pm-11:37 pm

1 stop11h 02m

$519

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 10/16

12:05 pm-12:33 pm

2 stops23h 28m

Simpson Bay Princess Juliana

Sat 10/24

1:35 pm-11:37 pm

1 stop11h 02m

$524

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 10/16

2:20 pm-12:33 pm

2 stops21h 13m

Simpson Bay Princess Juliana

Sat 10/24

1:35 pm-8:36 am

2 stops20h 01m

$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

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

$542

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 2/21

6:30 pm-2:35 pm

2 stops18h 05m

Simpson Bay Princess Juliana

Fri 2/26

2:55 pm-11:20 pm

1 stop10h 25m

$549

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 10/30

5:47 pm-3:39 pm

2 stops20h 52m

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-11:03 am

2 stops19h 30m

$560

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 11/6

7:29 pm-4:31 pm

2 stops19h 02m

Simpson Bay Princess Juliana

Fri 11/13

3:41 pm-7:48 am

2 stops18h 07m

$560

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 3/23

6:40 pm-11:30 am

2 stops15h 50m

Simpson Bay Princess Juliana

Sat 4/3

4:20 pm-9:22 am

1 stop18h 02m

$678

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 $519.

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	$519
Fastest flight time	7h 10m
Direct flights	None

The best flight deal from Milwaukee to Simpson Bay found on momondo in the last 72 hours is $519

The fastest flight from Milwaukee to Simpson Bay takes 7h 10m

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 10m.
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 10,226 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,591 reviews	Search Delta flights
Southwest	PriceFrom $526	Free Cancellation	Rating 8.0 4,198 reviews	Search Southwest flights
American Airlines	PriceFrom $612	Free Cancellation	Rating 7.0 12,076 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 $519

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 10/30. 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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Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Southwest flights from Milwaukee to Simpson Bay

Our best Southwest deals on Milwaukee to Simpson Bay flight tickets

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See travel insights to Simpson Bay from

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