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, American Airlines, and WestJet 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 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.

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: 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.

$519 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

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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

3:05 pm - 11:55 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 50m1 stop Orlando

$519Southwest

Sun, Oct 4 - Sun, Oct 11

5:20 am - 2:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 20m1 stop Atlanta Hartsfield-Jackson

4:05 pm - 11:54 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 49m1 stop Atlanta Hartsfield-Jackson

$519Delta

Sun, Nov 15 - Wed, Nov 18

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

8h 05m1 stop Orlando

3:05 pm - 12:15 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 10m2 stops Orlando Nashville Intl

$524Southwest

Sun, Oct 4 - Sun, Oct 11

6:05 pm - 2:05 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 00m2 stops Denver Intl Orlando

3:05 pm - 12:15 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 10m2 stops Orlando Nashville Intl

$524Southwest

Sun, Oct 4 - Sun, Oct 11

12:20 pm - 12:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 55m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

5:25 pm - 11:49 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 24m1 stop Atlanta Hartsfield-Jackson

$529Delta

Tue, Jan 12 - Sat, Jan 16

12:20 pm - 12:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 55m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

5:25 pm - 11:49 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 24m1 stop Atlanta Hartsfield-Jackson

$531Delta

Tue, Jan 12 - Sat, Jan 16

2:58 pm - 2:30 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

22h 32m2 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

$548American Airlines

Sat, Oct 31 - Sat, Nov 7

2:58 pm - 2:30 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

22h 32m2 stops Chicago O'Hare Intl Charlotte Douglas

4:20 pm - 11:06 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 46m1 stop Charlotte Douglas

$548American Airlines

Sat, Oct 31 - Sat, Nov 7

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

5:00 pm - 9:49 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

18h 49m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

$558United Airlines

Thu, Feb 25 - Sat, Mar 6

6:18 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 32m2 stops Chicago O'Hare Intl Newark

2:52 pm - 10:13 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 21m2 stops Newark Chicago O'Hare Intl

$604United Airlines

Sun, Nov 15 - Wed, Nov 18

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Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Delta

Jan 12

MKE12:20 pmMilwaukee-Mitchell

21h 55m

2 stops

SXM12:15 pmSimpson Bay Princess Juliana

Jan 16

SXM5:25 pmSimpson Bay Princess Juliana

8h 24m

1 stop

MKE11:49 pmMilwaukee-Mitchell

$529

Delta

Jan 12

MKE12:20 pmMilwaukee-Mitchell

21h 55m

2 stops

SXM12:15 pmSimpson Bay Princess Juliana

Jan 16

SXM5:25 pmSimpson Bay Princess Juliana

8h 24m

1 stop

MKE11:49 pmMilwaukee-Mitchell

$531

Delta

Jan 12

MKE6:40 pmMilwaukee-Mitchell

18h 00m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

Jan 16

SXM5:25 pmSimpson Bay Princess Juliana

8h 24m

1 stop

MKE11:49 pmMilwaukee-Mitchell

$567

American Airlines flights from Milwaukee to Simpson Bay

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

American Airlines

Oct 31

MKE2:58 pmMilwaukee-Mitchell

22h 32m

2 stops

SXM2:30 pmSimpson Bay Princess Juliana

Nov 7

SXM5:33 pmSimpson Bay Princess Juliana

18h 29m

2 stops

MKE10:02 amMilwaukee-Mitchell

$548

American Airlines

Nov 11

MKE2:55 pmMilwaukee-Mitchell

21h 31m

2 stops

SXM2:26 pmSimpson Bay Princess Juliana

Nov 17

SXM5:33 pmSimpson Bay Princess Juliana

19h 35m

2 stops

MKE11:08 amMilwaukee-Mitchell

$553

American Airlines

Jan 12

MKE3:49 pmMilwaukee-Mitchell

20h 42m

2 stops

SXM2:31 pmSimpson Bay Princess Juliana

Jan 16

SXM5:33 pmSimpson Bay Princess Juliana

18h 19m

2 stops

MKE9:52 amMilwaukee-Mitchell

$555

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 10/4

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sun 10/11

3:05 pm-11:55 pm

1 stop9h 50m

$519

Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 11/15

5:20 am-2:40 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Wed 11/18

4:05 pm-11:54 pm

1 stop9h 49m

$519

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 10/4

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sun 10/11

3:05 pm-12:15 am

2 stops10h 10m

$524

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 10/4

6:05 pm-2:05 pm

2 stops19h 00m

Simpson Bay Princess Juliana

Sun 10/11

3:05 pm-12:15 am

2 stops10h 10m

$524

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/12

12:20 pm-12:15 pm

2 stops21h 55m

Simpson Bay Princess Juliana

Sat 1/16

5:25 pm-11:49 pm

1 stop8h 24m

$529

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/12

12:20 pm-12:15 pm

2 stops21h 55m

Simpson Bay Princess Juliana

Sat 1/16

5:25 pm-11:49 pm

1 stop8h 24m

$531

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/31

2:58 pm-2:30 pm

2 stops22h 32m

Simpson Bay Princess Juliana

Sat 11/7

5:33 pm-10:02 am

2 stops18h 29m

$548

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/31

2:58 pm-2:30 pm

2 stops22h 32m

Simpson Bay Princess Juliana

Sat 11/7

4:20 pm-11:06 pm

1 stop8h 46m

$548

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Thu 2/25

7:00 pm-1:50 pm

2 stops16h 50m

Simpson Bay Princess Juliana

Sat 3/6

5:00 pm-9:49 am

2 stops18h 49m

$558

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 11/15

6:18 pm-1:50 pm

2 stops17h 32m

Simpson Bay Princess Juliana

Wed 11/18

2:52 pm-10:13 am

2 stops21h 21m

$604

Flights are sorted by cheapest round-trip flights first.

Sorted 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	$519
Fastest flight time	7h 00m
Direct flights	None

The best flight deal from Milwaukee to Simpson Bay found on momondo in the last 72 hours is $519

The fastest flight from Milwaukee to Simpson Bay takes 7h 00m

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 00m.
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 Delta (34% of total bookings). The next most popular airlines are American Airlines (32%), United Airlines (20%), and Southwest (14%).

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 10,157 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,538 reviews	Search Delta flights
Southwest	PriceFrom $596	Free Cancellation	Rating 8.0 4,191 reviews	Search Southwest flights
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 12,023 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 $519

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to Simpson Bay departing on 10/4. 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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Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

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?

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.

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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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