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.

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

Southwest and Delta are the most popular carriers operating from Milwaukee-Mitchell to Simpson Bay Princess Juliana

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.

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

Atlanta (ATL) was the most common stop: 82% 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 July 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.

$194 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

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:00 pm - 1:42 pm

MKE

SXM

17h 42m

2 stops

2:42 pm - 7:49 am

SXM

MKE

18h 07m

2 stops

$457American Airlines

Sat, Aug 22 - Fri, Aug 28

5:53 pm - 1:23 pm

MKE

SXM

18h 30m

2 stops

2:23 pm - 12:02 pm

SXM

MKE

22h 39m

2 stops

$470American Airlines

Mon, Sep 14 - Wed, Sep 23

7:20 pm - 2:05 pm

MKE

SXM

17h 45m

2 stops

3:05 pm - 10:25 pm

SXM

MKE

8h 20m

1 stop

$511Southwest

Sun, Aug 23 - Sun, Aug 30

6:20 pm - 2:05 pm

MKE

SXM

18h 45m

2 stops

3:05 pm - 10:25 pm

SXM

MKE

8h 20m

1 stop

$511Southwest

Sun, Aug 23 - Sun, Aug 30

5:30 am - 1:53 pm

MKE

SXM

7h 23m

1 stop

3:18 pm - 11:48 pm

SXM

MKE

9h 30m

1 stop

$515Delta

Mon, Sep 14 - Wed, Sep 23

5:30 am - 1:53 pm

MKE

SXM

7h 23m

1 stop

3:18 pm - 11:48 pm

SXM

MKE

9h 30m

1 stop

$523Delta

Mon, Sep 14 - Thu, Sep 24

7:00 am - 3:57 pm

MKE

SXM

6h 57m

1 stop

4:55 pm - 11:34 am

SXM

MKE

20h 39m

2 stops

$535United Airlines

Sat, Jan 23 - Sun, Jan 31

6:00 am - 3:57 pm

MKE

SXM

7h 57m

1 stop

5:00 pm - 9:49 am

SXM

MKE

18h 49m

2 stops

$538United Airlines

Sat, Dec 5 - Sat, Dec 12

5:00 am - 5:00 pm

MKE

SXM

35h 00m

2 stops

6:00 pm - 9:25 pm

SXM

MKE

28h 25m

2 stops

$1,166Air Canada

Fri, Sep 11 - Sat, Sep 26

8:30 am - 2:20 pm

MKE

SXM

28h 50m

3 stops

6:00 pm - 8:05 pm

SXM

MKE

27h 05m

3 stops

$1,353Multiple Airlines

Sat, Sep 5 - Sat, Sep 12

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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

Aug 22

MKE7:00 pmMilwaukee-Mitchell

17h 42m

2 stops

SXM1:42 pmSimpson Bay Princess Juliana

Aug 28

SXM2:42 pmSimpson Bay Princess Juliana

18h 07m

2 stops

MKE7:49 amMilwaukee-Mitchell

$457

American Airlines

Sep 14

MKE5:53 pmMilwaukee-Mitchell

18h 30m

2 stops

SXM1:23 pmSimpson Bay Princess Juliana

Sep 23

SXM2:23 pmSimpson Bay Princess Juliana

22h 39m

2 stops

MKE12:02 pmMilwaukee-Mitchell

$470

American Airlines

Sep 12

MKE5:53 pmMilwaukee-Mitchell

18h 30m

2 stops

SXM1:23 pmSimpson Bay Princess Juliana

Sep 19

SXM2:23 pmSimpson Bay Princess Juliana

21h 44m

2 stops

MKE11:07 amMilwaukee-Mitchell

$510

Southwest flights from Milwaukee to Simpson Bay

Our best Southwest deals on Milwaukee to Simpson Bay flight tickets

Southwest

Aug 23

MKE7:20 pmMilwaukee-Mitchell

17h 45m

2 stops

SXM2:05 pmSimpson Bay Princess Juliana

Aug 30

SXM3:05 pmSimpson Bay Princess Juliana

8h 20m

1 stop

MKE10:25 pmMilwaukee-Mitchell

$511

Southwest

Oct 18

MKE8:10 pmMilwaukee-Mitchell

16h 55m

2 stops

SXM2:05 pmSimpson Bay Princess Juliana

Oct 23

SXM3:05 pmSimpson Bay Princess Juliana

23h 05m

2 stops

MKE1:10 pmMilwaukee-Mitchell

$528

Southwest

Jan 23

MKE5:00 amMilwaukee-Mitchell

7h 50m

1 stop

SXM2:50 pmSimpson Bay Princess Juliana

Jan 31

SXM3:35 pmSimpson Bay Princess Juliana

10h 20m

1 stop

MKE11:55 pmMilwaukee-Mitchell

$530

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 8/22

7:00 pm-1:42 pm

2 stops17h 42m

Simpson Bay Princess Juliana

Fri 8/28

2:42 pm-7:49 am

2 stops18h 07m

$457

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 9/14

5:53 pm-1:23 pm

2 stops18h 30m

Simpson Bay Princess Juliana

Wed 9/23

2:23 pm-12:02 pm

2 stops22h 39m

$470

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 8/23

7:20 pm-2:05 pm

2 stops17h 45m

Simpson Bay Princess Juliana

Sun 8/30

3:05 pm-10:25 pm

1 stop8h 20m

$511

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 8/23

6:20 pm-2:05 pm

2 stops18h 45m

Simpson Bay Princess Juliana

Sun 8/30

3:05 pm-10:25 pm

1 stop8h 20m

$511

Quickest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 9/14

5:30 am-1:53 pm

1 stop7h 23m

Simpson Bay Princess Juliana

Wed 9/23

3:18 pm-11:48 pm

1 stop9h 30m

$515

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 9/14

5:30 am-1:53 pm

1 stop7h 23m

Simpson Bay Princess Juliana

Thu 9/24

3:18 pm-11:48 pm

1 stop9h 30m

$523

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 1/23

7:00 am-3:57 pm

1 stop6h 57m

Simpson Bay Princess Juliana

Sun 1/31

4:55 pm-11:34 am

2 stops20h 39m

$535

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 12/5

6:00 am-3:57 pm

1 stop7h 57m

Simpson Bay Princess Juliana

Sat 12/12

5:00 pm-9:49 am

2 stops18h 49m

$538

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 9/11

5:00 am-5:00 pm

2 stops35h 00m

Simpson Bay Princess Juliana

Sat 9/26

6:00 pm-9:25 pm

2 stops28h 25m

$1,166

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 9/5

8:30 am-2:20 pm

3 stops28h 50m

Simpson Bay Princess Juliana

Sat 9/12

6:00 pm-8:05 pm

3 stops27h 05m

$1,353

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 July 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 (37% of total bookings). The next most popular airlines are Delta (31%), 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 10,053 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,493 reviews	Search Delta flights
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 11,845 reviews	Search American Airlines flights
Southwest	PriceFrom $665	Free Cancellation	Rating 8.0 4,228 reviews	Search Southwest 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.

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Cheap flights from Milwaukee to Simpson Bay from $194

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 1/20. 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

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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

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Fly your favorite airline to Simpson Bay

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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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