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

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

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 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

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 October 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.

$241 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.

12:10 pm - 12:34 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

22h 24m2 stops Charlotte Douglas Miami

4:36 pm - 9:19 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 43m2 stops Charlotte Douglas Chicago O'Hare Intl

$559American Airlines

Tue, Jan 12 - Sat, Jan 16

2:09 pm - 12:34 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 25m2 stops Dallas/Fort Worth Miami

3:57 pm - 10:36 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 39m1 stop Chicago O'Hare Intl

$559American Airlines

Tue, Jan 12 - Sat, Jan 16

2:40 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 10m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

2:52 pm - 12:05 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

23h 13m2 stops Newark Chicago O'Hare Intl

$571United Airlines

Sat, Jan 30 - Fri, Feb 5

5:00 am - 3:57 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

8h 57m1 stop Chicago O'Hare Intl

2:52 pm - 2:00 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

25h 08m2 stops Newark Chicago O'Hare Intl

$571United Airlines

Sat, Jan 30 - Fri, Feb 5

5:10 am - 3:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

8h 30m1 stop Orlando

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

9h 00m1 stop Baltimore/Washington

$584Southwest

Sun, Dec 13 - Sun, Dec 20

5:15 am - 2:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 00m1 stop Orlando

3:15 pm - 9:45 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 30m1 stop Orlando

$587Southwest

Tue, Jan 12 - Sat, Jan 16

5:30 am - 2:57 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 27m1 stop Atlanta Hartsfield-Jackson

1:50 pm - 11:59 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

12h 09m1 stop Atlanta Hartsfield-Jackson

$607Delta

Sat, Jan 30 - Fri, Feb 5

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

7h 00m1 stop Atlanta Hartsfield-Jackson

3:20 pm - 4:45 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

26h 25m2 stops New York John F Kennedy Intl Minneapolis St Paul

$611Delta

Tue, Mar 9 - Tue, Mar 16

10:52 am - 3:45 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

26h 53m2 stops Fort Myers SW Florida Intl Toronto Pearson Intl

6:10 pm - 5:36 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

25h 26m3 stops Port of Spain Piarco Intl New York John F Kennedy Intl Minneapolis St Paul

$1,636Multiple Airlines

Sat, Dec 19 - Sat, Dec 26

10:45 am - 2:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

26h 55m3 stops Chicago O'Hare Intl Vancouver Intl Toronto Pearson Intl

2:40 pm - 11:27 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

33h 47m2 stops Montreal Pierre Elliott Trudeau Intl Orlando

$1,652Multiple Airlines

Sat, Mar 20 - Sat, Mar 27

Cheap last minute flights

Enter your travel dates to find the best prices.

5:47 pm - 2:30 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 43m2 stops Dallas/Fort Worth Charlotte Douglas

3:26 pm - 10:28 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 02m1 stop Miami

$900American Airlines

Sat, Oct 31 - Sat, Nov 7

7:19 pm - 4:31 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 12m2 stops Chicago O'Hare Intl Miami

3:26 pm - 7:48 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 22m2 stops Miami Chicago O'Hare Intl

$900American Airlines

Sat, Oct 31 - Sat, Nov 7

5:47 pm - 4:31 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 44m2 stops Dallas/Fort Worth Miami

5:33 pm - 10:02 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 29m2 stops Miami Charlotte Douglas

$920American Airlines

Sat, Oct 31 - Sat, Nov 7

7:19 pm - 4:31 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 12m2 stops Chicago O'Hare Intl Miami

3:26 pm - 7:48 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 22m2 stops Miami Chicago O'Hare Intl

$920American Airlines

Sat, Oct 31 - Sat, Nov 7

5:47 pm - 2:30 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 43m2 stops Dallas/Fort Worth Charlotte Douglas

3:26 pm - 10:28 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 02m1 stop Miami

$920American Airlines

Sat, Oct 31 - Sat, Nov 7

6:48 am - 2:57 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 09m1 stop Chicago O'Hare Intl

2:10 pm - 8:50 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 40m1 stop Chicago O'Hare Intl

$948United Airlines

Sat, Oct 31 - Sat, Nov 7

6:48 am - 2:57 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 09m1 stop Chicago O'Hare Intl

2:10 pm - 8:50 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 40m1 stop Chicago O'Hare Intl

$983United Airlines

Sat, Oct 31 - Sat, Nov 7

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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

Jan 12

MKE12:10 pmMilwaukee-Mitchell

22h 24m

2 stops

SXM12:34 pmSimpson Bay Princess Juliana

Jan 16

SXM4:36 pmSimpson Bay Princess Juliana

18h 43m

2 stops

MKE9:19 amMilwaukee-Mitchell

$559

American Airlines

Jan 12

MKE12:10 pmMilwaukee-Mitchell

24h 49m

1 stop

SXM2:59 pmSimpson Bay Princess Juliana

Jan 16

SXM3:57 pmSimpson Bay Princess Juliana

8h 39m

1 stop

MKE10:36 pmMilwaukee-Mitchell

$563

American Airlines

Feb 6

MKE5:17 amMilwaukee-Mitchell

7h 50m

1 stop

SXM3:07 pmSimpson Bay Princess Juliana

Feb 11

SXM3:23 pmSimpson Bay Princess Juliana

10h 31m

1 stop

MKE11:54 pmMilwaukee-Mitchell

$577

Southwest flights from Milwaukee to Simpson Bay

Our best Southwest deals on Milwaukee to Simpson Bay flight tickets

Southwest

Dec 13

MKE5:10 amMilwaukee-Mitchell

8h 30m

1 stop

SXM3:40 pmSimpson Bay Princess Juliana

Dec 20

SXM4:40 pmSimpson Bay Princess Juliana

9h 00m

1 stop

MKE11:40 pmMilwaukee-Mitchell

$584

Southwest

Jan 12

MKE5:15 amMilwaukee-Mitchell

7h 00m

1 stop

SXM2:15 pmSimpson Bay Princess Juliana

Jan 16

SXM3:15 pmSimpson Bay Princess Juliana

8h 30m

1 stop

MKE9:45 pmMilwaukee-Mitchell

$587

Southwest

Nov 22

MKE5:10 amMilwaukee-Mitchell

8h 30m

1 stop

SXM3:40 pmSimpson Bay Princess Juliana

Nov 29

SXM4:40 pmSimpson Bay Princess Juliana

18h 35m

2 stops

MKE9:15 amMilwaukee-Mitchell

$696

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/12

12:10 pm-12:34 pm

2 stops22h 24m

Simpson Bay Princess Juliana

Sat 1/16

4:36 pm-9:19 am

2 stops18h 43m

$559

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/12

2:09 pm-12:34 pm

2 stops20h 25m

Simpson Bay Princess Juliana

Sat 1/16

3:57 pm-10:36 pm

1 stop8h 39m

$559

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

2:40 pm-1:50 pm

2 stops21h 10m

Simpson Bay Princess Juliana

Fri 2/5

2:52 pm-12:05 pm

2 stops23h 13m

$571

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

5:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Fri 2/5

2:52 pm-2:00 pm

2 stops25h 08m

$571

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 12/13

5:10 am-3:40 pm

1 stop8h 30m

Simpson Bay Princess Juliana

Sun 12/20

4:40 pm-11:40 pm

1 stop9h 00m

$584

Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/12

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 1/16

3:15 pm-9:45 pm

1 stop8h 30m

$587

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

5:30 am-2:57 pm

1 stop7h 27m

Simpson Bay Princess Juliana

Fri 2/5

1:50 pm-11:59 pm

1 stop12h 09m

$607

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 3/9

5:55 am-2:55 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Tue 3/16

3:20 pm-4:45 pm

2 stops26h 25m

$611

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 12/19

10:52 am-3:45 pm

2 stops26h 53m

Simpson Bay Princess Juliana

Sat 12/26

6:10 pm-5:36 pm

3 stops25h 26m

$1,636

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 3/20

10:45 am-2:40 pm

3 stops26h 55m

Simpson Bay Princess Juliana

Sat 3/27

2:40 pm-11:27 pm

2 stops33h 47m

$1,652

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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

Best Price Found	$241
Fastest flight time	7h 09m
Direct flights	None

The best one-way flight to Simpson Bay from Milwaukee in the past 72 hours is $241. The best round-trip flight deal from Milwaukee to Simpson Bay found on momondo in the last 72 hours is $559.

The fastest flight from Milwaukee to Simpson Bay takes 7h 09m

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 09m.
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 October 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 (29% of total bookings). The next most popular airlines are American Airlines (27%), United Airlines (22%), and Southwest (22%).

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 7.3 10,444 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,681 reviews	Search Delta flights
Southwest	PriceFrom $526	Free Cancellation	Rating 7.9 4,218 reviews	Search Southwest flights
American Airlines	PriceFrom $612	Free Cancellation	Rating 7.0 12,197 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 $241

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 12/11. 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

Southwest 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

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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