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

Atlanta (ATL) was the most common stop: 86% 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?

Chicago (ORD) has the shortest average layover time for this route: 2h 09m.

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 56% 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.

What is the cheapest airline that flies from Milwaukee-Mitchell to Simpson Bay Princess Juliana?

American Airlines is the most popular carrier operating from Milwaukee-Mitchell to Simpson Bay Princess Juliana

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 August 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.

$213 Cheap Flights from Milwaukee to Simpson Bay in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Milwaukee to Simpson Bay

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2:58 pm - 1:23 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 25m2 stops Chicago O'Hare Intl Miami

4:39 pm - 8:07 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

16h 28m2 stops Miami Chicago O'Hare Intl

$484American Airlines

Sat, Oct 24 - Wed, Oct 28

6:30 am - 4:28 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 58m1 stop Miami

3:31 pm - 10:58 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 27m1 stop Miami

$486American Airlines

Tue, Jan 19 - Wed, Jan 27

6:30 am - 4:28 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 58m1 stop Miami

2:03 pm - 10:58 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 55m1 stop Miami

$486American Airlines

Tue, Jan 26 - Wed, Feb 3

6:38 pm - 12:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 12m1 stop Newark

1:52 pm - 11:04 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 12m1 stop Newark

$517United Airlines

Sat, Oct 24 - Wed, Oct 28

6:38 pm - 12:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 12m1 stop Newark

1:52 pm - 11:04 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 12m1 stop Newark

$517United Airlines

Sat, Oct 24 - Wed, Oct 28

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

$522Delta

Mon, Jan 25 - Thu, Jan 28

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

$522Delta

Sun, Jan 17 - Wed, Jan 27

5:00 am - 2:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 50m1 stop Orlando

3:35 pm - 11:55 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 20m1 stop Orlando

$554Southwest

Sat, Jan 30 - Mon, Feb 8

5:00 am - 2:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 50m1 stop Orlando

2:30 pm - 9:20 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 50m1 stop Orlando

$566Southwest

Sat, Feb 6 - Sat, Feb 13

5:10 pm - 3:39 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 29m2 stops Washington, D.C. Reagan-National Miami

4:39 pm - 11:26 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

19h 47m2 stops Miami Charlotte Douglas

$667British Airways

Sun, Oct 18 - Mon, Oct 26

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American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets

American Airlines

Oct 24

MKE2:58 pmMilwaukee-Mitchell

21h 25m

2 stops

SXM1:23 pmSimpson Bay Princess Juliana

Oct 28

SXM4:39 pmSimpson Bay Princess Juliana

16h 28m

2 stops

MKE8:07 amMilwaukee-Mitchell

$484

American Airlines

Jan 19

MKE6:30 amMilwaukee-Mitchell

7h 58m

1 stop

SXM4:28 pmSimpson Bay Princess Juliana

Jan 27

SXM3:31 pmSimpson Bay Princess Juliana

9h 27m

1 stop

MKE10:58 pmMilwaukee-Mitchell

$486

American Airlines

Jan 19

MKE6:30 amMilwaukee-Mitchell

7h 58m

1 stop

SXM4:28 pmSimpson Bay Princess Juliana

Jan 27

SXM5:33 pmSimpson Bay Princess Juliana

19h 39m

2 stops

MKE11:12 amMilwaukee-Mitchell

$491

United Airlines flights from Milwaukee to Simpson Bay

Our best United Airlines deals on Milwaukee to Simpson Bay flight tickets

United Airlines

Oct 24

MKE6:38 pmMilwaukee-Mitchell

17h 12m

1 stop

SXM12:50 pmSimpson Bay Princess Juliana

Oct 28

SXM1:52 pmSimpson Bay Princess Juliana

10h 12m

1 stop

MKE11:04 pmMilwaukee-Mitchell

$517

United Airlines

Jan 23

MKE7:00 pmMilwaukee-Mitchell

16h 50m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

Jan 30

SXM2:40 pmSimpson Bay Princess Juliana

9h 59m

1 stop

MKE10:39 pmMilwaukee-Mitchell

$526

United Airlines

Feb 6

MKE7:00 pmMilwaukee-Mitchell

16h 50m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

Feb 13

SXM5:00 pmSimpson Bay Princess Juliana

18h 49m

2 stops

MKE9:49 amMilwaukee-Mitchell

$594

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/24

2:58 pm-1:23 pm

2 stops21h 25m

Simpson Bay Princess Juliana

Wed 10/28

4:39 pm-8:07 am

2 stops16h 28m

$484

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/19

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Wed 1/27

3:31 pm-10:58 pm

1 stop9h 27m

$486

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/26

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Wed 2/3

2:03 pm-10:58 pm

1 stop10h 55m

$486

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/24

6:38 pm-12:50 pm

1 stop17h 12m

Simpson Bay Princess Juliana

Wed 10/28

1:52 pm-11:04 pm

1 stop10h 12m

$517

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/24

6:38 pm-12:50 pm

1 stop17h 12m

Simpson Bay Princess Juliana

Wed 10/28

1:52 pm-11:04 pm

1 stop10h 12m

$517

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Mon 1/25

6:40 pm-2:40 pm

1 stop18h 00m

Simpson Bay Princess Juliana

Thu 1/28

1:40 pm-11:49 pm

1 stop12h 09m

$522

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 1/17

6:40 pm-2:40 pm

1 stop18h 00m

Simpson Bay Princess Juliana

Wed 1/27

1:40 pm-11:49 pm

1 stop12h 09m

$522

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

5:00 am-2:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Mon 2/8

3:35 pm-11:55 pm

1 stop10h 20m

$554

Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 2/6

5:00 am-2:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sat 2/13

2:30 pm-9:20 pm

1 stop8h 50m

$566

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 10/18

5:10 pm-3:39 pm

2 stops21h 29m

Simpson Bay Princess Juliana

Mon 10/26

4:39 pm-11:26 am

2 stops19h 47m

$667

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted 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 $613 to $713.
The lowest price recently found on this route was $484.

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	$213
Fastest flight time	7h 10m
Direct flights	None

The best one-way flight to Simpson Bay from Milwaukee in the past 72 hours is $213. The best round-trip flight deal from Milwaukee to Simpson Bay found on momondo in the last 72 hours is $484.

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 August 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 American Airlines (34% of total bookings). The next most popular airlines are Delta (34%), United Airlines (19%), and Southwest (13%).

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 10,121 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,530 reviews	Search Delta flights
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 11,994 reviews	Search American Airlines flights
Southwest	PriceFrom $665	Free Cancellation	Rating 8.0 4,205 reviews	Search Southwest flights

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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.

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Cheap flights from Milwaukee to Simpson Bay from $213

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to Simpson Bay departing on 2/20. 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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American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets

United Airlines flights from Milwaukee to Simpson Bay

Our best United Airlines 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 is the cheapest airline that flies from Milwaukee-Mitchell to Simpson Bay Princess Juliana?

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