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 offers the lowest fares from Milwaukee to Simpson Bay?

Flights via Chicago (ORD) offer the lowest average round-trip price of $521.

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

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

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 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.

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 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.

$327 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

Last minute

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

8h 50m1 stop Baltimore/Washington

$519Southwest

Mon, Oct 26 - Mon, Nov 2

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

$524Southwest

Mon, Oct 26 - Mon, Nov 2

6:40 am - 3:57 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 17m1 stop Chicago O'Hare Intl

2:10 pm - 7:11 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

19h 01m1 stop Chicago O'Hare Intl

$526United Airlines

Thu, Dec 31 - Sat, Jan 16

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

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

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

6:27 pm - 3:39 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

20h 12m2 stops Charlotte Douglas Miami

4:39 pm - 2:24 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

22h 45m2 stops Miami Chicago O'Hare Intl

$544American Airlines

Sat, Oct 17 - Tue, Oct 20

6:40 pm - 2:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

18h 00m1 stop Atlanta Hartsfield-Jackson

1:40 pm - 11:49 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

12h 09m1 stop Atlanta Hartsfield-Jackson

$546Delta

Sun, Feb 7 - Fri, Feb 12

5:00 am - 2:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 50m1 stop Orlando

3:35 pm - 11:55 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 20m1 stop Orlando

$546Southwest

Sat, Jan 30 - Mon, Feb 8

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

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

2:24 pm - 11:06 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 42m1 stop Charlotte Douglas

$552American Airlines

Sat, Oct 31 - Sat, Nov 7

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Delta

Oct 9

MKE5:30 amMilwaukee-Mitchell

7h 10m

1 stop

SXM1:40 pmSimpson Bay Princess Juliana

Oct 16

SXM3:05 pmSimpson Bay Princess Juliana

9h 48m

1 stop

MKE11:53 pmMilwaukee-Mitchell

$539

Delta

Oct 23

MKE5:30 amMilwaukee-Mitchell

7h 10m

1 stop

SXM1:40 pmSimpson Bay Princess Juliana

Oct 30

SXM3:05 pmSimpson Bay Princess Juliana

9h 48m

1 stop

MKE11:53 pmMilwaukee-Mitchell

$560

Delta

Jan 21

MKE6:40 pmMilwaukee-Mitchell

18h 00m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

Jan 28

SXM1:40 pmSimpson Bay Princess Juliana

12h 09m

1 stop

MKE11:49 pmMilwaukee-Mitchell

$615

American Airlines flights from Milwaukee to Simpson Bay

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

American Airlines

Oct 17

MKE6:27 pmMilwaukee-Mitchell

20h 12m

2 stops

SXM3:39 pmSimpson Bay Princess Juliana

Oct 20

SXM4:39 pmSimpson Bay Princess Juliana

22h 45m

2 stops

MKE2:24 pmMilwaukee-Mitchell

$544

American Airlines

Oct 31

MKE11:33 amMilwaukee-Mitchell

25h 57m

2 stops

SXM2:30 pmSimpson Bay Princess Juliana

Nov 7

SXM2:24 pmSimpson Bay Princess Juliana

10h 42m

1 stop

MKE11:06 pmMilwaukee-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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

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

Mon 10/26

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 11/2

3:15 pm-11:55 pm

2 stops10h 40m

$524

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Thu 12/31

6:40 am-3:57 pm

1 stop7h 17m

Simpson Bay Princess Juliana

Sat 1/16

2:10 pm-7:11 am

1 stop19h 01m

$526

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

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

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 10/17

6:27 pm-3:39 pm

2 stops20h 12m

Simpson Bay Princess Juliana

Tue 10/20

4:39 pm-2:24 pm

2 stops22h 45m

$544

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 2/7

6:40 pm-2:40 pm

1 stop18h 00m

Simpson Bay Princess Juliana

Fri 2/12

1:40 pm-11:49 pm

1 stop12h 09m

$546

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 1/30

5:00 am-2:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Mon 2/8

3:35 pm-11:55 pm

1 stop10h 20m

$546

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

2:24 pm-11:06 pm

1 stop10h 42m

$552

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

Best Price Found	$327
Fastest flight time	7h 10m
Direct flights	None

The best one-way flight to Simpson Bay from Milwaukee in the past 72 hours is $327. The best round-trip 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 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 10,207 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.8 8,567 reviews	Search Delta flights
Southwest	PriceFrom $526	Free Cancellation	Rating 8.0 4,191 reviews	Search Southwest flights
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 12,051 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

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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Mon 10/12

Mon 10/19

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to St. Maarten

Airlines

Cabin classes

Other flights from Milwaukee

Complete your trip

Feeling lucky

Fly your favorite airline to Simpson Bay

Cheap flights from Milwaukee to Simpson Bay from $327

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 9/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Milwaukee to Simpson Bay

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

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

momondo Fare Finder

Use the filters below to find and compare flights from Milwaukee to Simpson Bay that are best for you.

See travel insights to Simpson Bay from

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.

Fly to other destinations from Milwaukee

According to popular flight searches on momondo this year

Complete your trip to Simpson Bay

Explore popular destinations other users love

According to popular flight searches on momondo this year