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?

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

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 55% 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?

Delta, United Airlines, and WestJet are the most popular carriers operating from Milwaukee-Mitchell to Simpson Bay Princess Juliana

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

Atlanta (ATL) was the most common stop: 83% of momondo users choosing 1-stop flights on this route connected there.

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 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.

$215 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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3:49 pm - 2:31 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 42m2 stops Charlotte Douglas Miami

5:33 pm - 11:12 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

19h 39m2 stops Miami Chicago O'Hare Intl

$456American Airlines

Thu, Feb 4 - Fri, Feb 12

3:49 pm - 1:45 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 56m1 stop Charlotte Douglas

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

16h 34m2 stops Miami Chicago O'Hare Intl

$465American Airlines

Thu, Feb 4 - Fri, Feb 12

5:55 pm - 12:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

16h 20m1 stop New York LaGuardia

4:05 pm - 12:27 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

22h 22m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County

$477Delta

Tue, Feb 2 - Tue, Feb 9

5:55 pm - 12:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

16h 20m1 stop New York LaGuardia

4:05 pm - 12:27 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

22h 22m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County

$477Delta

Sun, Jan 31 - Tue, Feb 9

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

$496American Airlines

Sat, Oct 24 - Wed, Oct 28

4:20 pm - 2:35 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 15m2 stops Las Vegas Harry Reid Intl Orlando

4:15 pm - 9:10 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 55m2 stops Baltimore/Washington Orlando

$504Southwest

Thu, Feb 4 - Fri, Feb 12

7:35 pm - 2:05 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 30m2 stops Las Vegas Harry Reid Intl Orlando

3:05 pm - 12:35 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 30m1 stop Orlando

$524Southwest

Thu, Oct 1 - Mon, Oct 5

7:00 pm - 3:48 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

18h 48m2 stops Chicago O'Hare Intl Newark

2:52 pm - 11:27 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 35m1 stop Newark

$531United Airlines

Wed, Jan 6 - Wed, Jan 13

7:00 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

16h 50m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

2:52 pm - 11:34 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

22h 42m2 stops Newark Chicago O'Hare Intl

$531United Airlines

Wed, Jan 6 - Wed, Jan 13

12:14 pm - 2:45 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

24h 31m2 stops Chicago O'Hare Intl Montreal Pierre Elliott Trudeau Intl

3:45 pm - 9:49 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

20h 04m2 stops Montreal Pierre Elliott Trudeau Intl Chicago O'Hare Intl

$2,467Air Canada

Fri, Jan 29 - Sat, Feb 6

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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

Feb 4

MKE3:49 pmMilwaukee-Mitchell

20h 42m

2 stops

SXM2:31 pmSimpson Bay Princess Juliana

Feb 12

SXM5:33 pmSimpson Bay Princess Juliana

19h 39m

2 stops

MKE11:12 amMilwaukee-Mitchell

$456

American Airlines

Feb 4

MKE3:49 pmMilwaukee-Mitchell

19h 56m

1 stop

SXM1:45 pmSimpson Bay Princess Juliana

Feb 12

SXM5:33 pmSimpson Bay Princess Juliana

16h 34m

2 stops

MKE8:07 amMilwaukee-Mitchell

$465

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

$496

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Delta

Jan 31

MKE5:00 pmMilwaukee-Mitchell

17h 15m

2 stops

SXM12:15 pmSimpson Bay Princess Juliana

Feb 10

SXM4:05 pmSimpson Bay Princess Juliana

22h 22m

2 stops

MKE12:27 pmMilwaukee-Mitchell

$477

Delta

Sep 21

MKE5:30 amMilwaukee-Mitchell

7h 23m

1 stop

SXM1:53 pmSimpson Bay Princess Juliana

Sep 26

SXM3:18 pmSimpson Bay Princess Juliana

9h 30m

1 stop

MKE11:48 pmMilwaukee-Mitchell

$492

Delta

Jan 30

MKE6:40 pmMilwaukee-Mitchell

18h 00m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

Feb 4

SXM4:05 pmSimpson Bay Princess Juliana

22h 22m

2 stops

MKE12:27 pmMilwaukee-Mitchell

$504

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Thu 2/4

3:49 pm-2:31 pm

2 stops20h 42m

Simpson Bay Princess Juliana

Fri 2/12

5:33 pm-11:12 am

2 stops19h 39m

$456

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Thu 2/4

3:49 pm-1:45 pm

1 stop19h 56m

Simpson Bay Princess Juliana

Fri 2/12

5:33 pm-8:07 am

2 stops16h 34m

$465

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 2/2

5:55 pm-12:15 pm

1 stop16h 20m

Simpson Bay Princess Juliana

Tue 2/9

4:05 pm-12:27 pm

2 stops22h 22m

$477

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 1/31

5:55 pm-12:15 pm

1 stop16h 20m

Simpson Bay Princess Juliana

Tue 2/9

4:05 pm-12:27 pm

2 stops22h 22m

$477

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

$496

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Thu 2/4

4:20 pm-2:35 pm

2 stops20h 15m

Simpson Bay Princess Juliana

Fri 2/12

4:15 pm-9:10 am

2 stops18h 55m

$504

Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Thu 10/1

7:35 pm-2:05 pm

2 stops17h 30m

Simpson Bay Princess Juliana

Mon 10/5

3:05 pm-12:35 am

1 stop10h 30m

$524

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Wed 1/6

7:00 pm-3:48 pm

2 stops18h 48m

Simpson Bay Princess Juliana

Wed 1/13

2:52 pm-11:27 pm

1 stop10h 35m

$531

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Wed 1/6

7:00 pm-1:50 pm

2 stops16h 50m

Simpson Bay Princess Juliana

Wed 1/13

2:52 pm-11:34 am

2 stops22h 42m

$531

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 1/29

12:14 pm-2:45 pm

2 stops24h 31m

Simpson Bay Princess Juliana

Sat 2/6

3:45 pm-9:49 am

2 stops20h 04m

$2,467

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 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

Fastest flight time	7h 10m
Direct flights	None

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.

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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 (35% of total bookings). The next most popular airlines are Delta (33%), 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 10,095 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,497 reviews	Search Delta flights
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 11,897 reviews	Search American Airlines flights
Southwest	PriceFrom $665	Free Cancellation	Rating 8.0 4,218 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 $215

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 11/15. 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

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How to get the cheapest flight ticket from Milwaukee to 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

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.

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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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