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.

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 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.

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.

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

United Airlines, American 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.

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 November 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.

$255 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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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

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

7h 00m1 stop Orlando

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

8h 50m1 stop Baltimore/Washington

$592Southwest

Sun, Jan 10 - Mon, Jan 18

3:51 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 59m2 stops Chicago O'Hare Intl Newark

2:52 pm - 8:07 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

19h 15m2 stops Newark Chicago O'Hare Intl

$596United Airlines

Sun, Jan 10 - Sun, Jan 17

6:29 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 21m1 stop Newark

2:52 pm - 10:00 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 08m2 stops Newark Chicago O'Hare Intl

$596United Airlines

Sun, Jan 10 - Sun, Jan 17

4:25 pm - 2:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 50m2 stops Las Vegas Harry Reid Intl Orlando

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

8h 50m1 stop Baltimore/Washington

$596Southwest

Sun, Jan 10 - Mon, Jan 18

5:30 am - 2:49 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 19m1 stop Atlanta Hartsfield-Jackson

1:40 pm - 11:59 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

12h 19m1 stop Atlanta Hartsfield-Jackson

$632Delta

Wed, Dec 23 - Wed, Dec 30

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

7h 20m1 stop Atlanta Hartsfield-Jackson

1:40 pm - 8:48 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 08m1 stop Atlanta Hartsfield-Jackson

$632Delta

Tue, Dec 15 - Tue, Dec 22

8:30 am - 3:25 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

28h 55m3 stops Chicago O'Hare Intl Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

4:50 pm - 6:19 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

27h 29m3 stops Toronto Pearson Intl Miami Minneapolis St Paul

$1,121Multiple Airlines

Tue, Dec 15 - Tue, Dec 22

12:15 pm - 11:55 amMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 40m2 stops Chicago O'Hare Intl Montreal Pierre Elliott Trudeau Intl

4:50 pm - 6:19 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

27h 29m3 stops Toronto Pearson Intl Miami Minneapolis St Paul

$1,234Multiple Airlines

Tue, Dec 15 - Tue, Dec 22

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Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Delta

Dec 15

MKE5:20 amMilwaukee-Mitchell

7h 20m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

Dec 22

SXM1:40 pmSimpson Bay Princess Juliana

9h 08m

1 stop

MKE8:48 pmMilwaukee-Mitchell

$632

Delta

Mar 30

MKE5:55 amMilwaukee-Mitchell

7h 00m

1 stop

SXM1:55 pmSimpson Bay Princess Juliana

Apr 7

SXM12:55 pmSimpson Bay Princess Juliana

9h 13m

1 stop

MKE9:08 pmMilwaukee-Mitchell

$640

Delta

Mar 30

MKE1:20 pmMilwaukee-Mitchell

21h 10m

2 stops

SXM11:30 amSimpson Bay Princess Juliana

Apr 6

SXM3:20 pmSimpson Bay Princess Juliana

26h 25m

2 stops

MKE4:45 pmMilwaukee-Mitchell

$644

United Airlines flights from Milwaukee to Simpson Bay

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

United Airlines

Apr 30

MKE3:33 pmMilwaukee-Mitchell

20h 00m

2 stops

SXM12:33 pmSimpson Bay Princess Juliana

May 8

SXM3:50 pmSimpson Bay Princess Juliana

17h 44m

2 stops

MKE8:34 amMilwaukee-Mitchell

$611

United Airlines

Dec 14

MKE7:10 pmMilwaukee-Mitchell

16h 40m

1 stop

SXM1:50 pmSimpson Bay Princess Juliana

Dec 21

SXM2:10 pmSimpson Bay Princess Juliana

11h 01m

1 stop

MKE11:11 pmMilwaukee-Mitchell

$620

United Airlines

Jan 9

MKE2:40 pmMilwaukee-Mitchell

21h 10m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

Jan 16

SXM5:00 pmSimpson Bay Princess Juliana

23h 00m

2 stops

MKE2:00 pmMilwaukee-Mitchell

$626

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

Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 1/10

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 1/18

4:40 pm-11:30 pm

1 stop8h 50m

$592

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 1/10

3:51 pm-1:50 pm

2 stops19h 59m

Simpson Bay Princess Juliana

Sun 1/17

2:52 pm-8:07 am

2 stops19h 15m

$596

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 1/10

6:29 pm-1:50 pm

1 stop17h 21m

Simpson Bay Princess Juliana

Sun 1/17

2:52 pm-10:00 am

2 stops21h 08m

$596

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 1/10

4:25 pm-2:15 pm

2 stops19h 50m

Simpson Bay Princess Juliana

Mon 1/18

4:40 pm-11:30 pm

1 stop8h 50m

$596

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Wed 12/23

5:30 am-2:49 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Wed 12/30

1:40 pm-11:59 pm

1 stop12h 19m

$632

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 12/15

5:20 am-2:40 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Tue 12/22

1:40 pm-8:48 pm

1 stop9h 08m

$632

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 12/15

8:30 am-3:25 pm

3 stops28h 55m

Simpson Bay Princess Juliana

Tue 12/22

4:50 pm-6:19 pm

3 stops27h 29m

$1,121

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 12/15

12:15 pm-11:55 am

2 stops21h 40m

Simpson Bay Princess Juliana

Tue 12/22

4:50 pm-6:19 pm

3 stops27h 29m

$1,234

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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	$255
Fastest flight time	7h 09m
Direct flights	None

The best one-way flight to Simpson Bay from Milwaukee in the past 72 hours is $255. 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 November 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 (30% of total bookings). The next most popular airlines are Delta (29%), United Airlines (21%), and Southwest (21%).

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 10,460 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,696 reviews	Search Delta flights
Southwest	PriceFrom $526	Free Cancellation	Rating 8.0 4,215 reviews	Search Southwest flights
American Airlines	PriceFrom $612	Free Cancellation	Rating 7.0 12,230 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 $255

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 1/1. 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

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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

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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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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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