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.

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 5 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: 87% of momondo users choosing 1-stop flights on this route connected there.

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.

$401 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

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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

$486Southwest

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

$491Southwest

Fri, Oct 30 - Fri, Nov 6

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

8h 05m1 stop Orlando

4:40 pm - 11:30 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 50m1 stop Baltimore/Washington

$519Southwest

Mon, Oct 26 - Mon, Nov 2

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

8h 57m1 stop Chicago O'Hare Intl

2:52 pm - 2:01 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

25h 09m2 stops Newark Chicago O'Hare Intl

$531United Airlines

Sat, Jan 9 - Fri, Jan 15

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

2:52 pm - 9:52 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 00m2 stops Newark Chicago O'Hare Intl

$531United Airlines

Sat, Jan 9 - Fri, Jan 15

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

8h 57m1 stop Chicago O'Hare Intl

2:52 pm - 9:52 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 00m2 stops Newark Chicago O'Hare Intl

$531United Airlines

Sat, Jan 9 - Fri, Jan 15

5:30 am - 1:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 10m1 stop Atlanta Hartsfield-Jackson

4:05 pm - 11:53 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 48m1 stop Atlanta Hartsfield-Jackson

$539Delta

Wed, Oct 28 - Wed, Nov 4

5:30 am - 1:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 10m1 stop Atlanta Hartsfield-Jackson

3:05 pm - 11:53 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 48m1 stop Atlanta Hartsfield-Jackson

$539Delta

Fri, Oct 9 - Fri, Oct 16

11:33 am - 2:30 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

25h 57m2 stops Chicago O'Hare Intl Charlotte Douglas

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

18h 29m2 stops Miami Charlotte Douglas

$552American 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

$552American 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

Oct 31

MKE11:33 amMilwaukee-Mitchell

25h 57m

2 stops

SXM2:30 pmSimpson Bay Princess Juliana

Nov 7

SXM5:33 pmSimpson Bay Princess Juliana

18h 29m

2 stops

MKE10:02 amMilwaukee-Mitchell

$552

American Airlines

Jan 12

MKE12:10 pmMilwaukee-Mitchell

22h 16m

2 stops

SXM12:26 pmSimpson Bay Princess Juliana

Jan 16

SXM4:02 pmSimpson Bay Princess Juliana

19h 09m

2 stops

MKE9:11 amMilwaukee-Mitchell

$559

American Airlines

Oct 13

MKE2:58 pmMilwaukee-Mitchell

21h 25m

2 stops

SXM1:23 pmSimpson Bay Princess Juliana

Oct 20

SXM4:39 pmSimpson Bay Princess Juliana

19h 52m

2 stops

MKE11:31 amMilwaukee-Mitchell

$564

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

$486

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

$491

Southwest

Oct 26

MKE5:00 amMilwaukee-Mitchell

8h 05m

1 stop

SXM2:05 pmSimpson Bay Princess Juliana

Nov 2

SXM4:40 pmSimpson Bay Princess Juliana

8h 50m

1 stop

MKE11:30 pmMilwaukee-Mitchell

$519

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

$486

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

$491

Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Mon 10/26

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 11/2

4:40 pm-11:30 pm

1 stop8h 50m

$519

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/9

5:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Fri 1/15

2:52 pm-2:01 pm

2 stops25h 09m

$531

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/9

3:42 pm-1:50 pm

2 stops20h 08m

Simpson Bay Princess Juliana

Fri 1/15

2:52 pm-9:52 am

2 stops21h 00m

$531

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/9

5:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Fri 1/15

2:52 pm-9:52 am

2 stops21h 00m

$531

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Wed 10/28

5:30 am-1:40 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Wed 11/4

4:05 pm-11:53 pm

1 stop9h 48m

$539

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Fri 10/9

5:30 am-1:40 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Fri 10/16

3:05 pm-11:53 pm

1 stop9h 48m

$539

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/31

11:33 am-2:30 pm

2 stops25h 57m

Simpson Bay Princess Juliana

Sat 11/7

5:33 pm-10:02 am

2 stops18h 29m

$552

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/31

5:47 pm-2:30 pm

2 stops19h 43m

Simpson Bay Princess Juliana

Sat 11/7

3:26 pm-10:28 pm

1 stop9h 02m

$552

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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	$401
Fastest flight time	7h 10m
Direct flights	None

The best one-way flight to Simpson Bay from Milwaukee in the past 72 hours is $401. The best round-trip flight deal from Milwaukee to Simpson Bay found on momondo in the last 72 hours is $486.

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 American Airlines (32% of total bookings). The next most popular airlines are Delta (32%), 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 10,208 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,568 reviews	Search Delta flights
Southwest	PriceFrom $526	Free Cancellation	Rating 8.0 4,190 reviews	Search Southwest flights
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 12,058 reviews	Search American Airlines 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 $401

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 11/12. 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

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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?

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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

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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.

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

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

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