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 48% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 4 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

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 2 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of September 2025.

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.

$434 Cheap Flights from Milwaukee to Simpson Bay in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

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

Find the cheapest flights from Milwaukee to Simpson Bay

Round-trip

One-way

Last minute

Cheap round-trip flights

6:39 pm - 2:57 pmMKE-SXM

19h 18m1 stop

2:52 pm - 11:29 amSXM-MKE

22h 37m2 stops

$527United Airlines

Find Deal

Fri, Oct 31 - Tue, Nov 4

3:50 pm - 1:50 pmMKE-SXM

20h 00m2 stops

2:40 pm - 10:13 pmSXM-MKE

9h 33m1 stop

$637United Airlines

Find Deal

Fri, Dec 12 - Sat, Dec 20

7:19 pm - 3:08 pmMKE-SXM

17h 49m1 stop

3:28 pm - 11:59 pmSXM-MKE

10h 31m1 stop

$655American Airlines

Find Deal

Fri, Dec 12 - Sat, Dec 20

12:20 pm - 1:37 pmMKE-SXM

24h 17m2 stops

5:24 pm - 12:01 pmSXM-MKE

20h 37m2 stops

$657American Airlines

Find Deal

Fri, Oct 31 - Tue, Nov 4

5:00 am - 4:25 pmMKE-SXM

9h 25m2 stops

5:33 pm - 11:03 amSXM-MKE

19h 30m2 stops

$660American Airlines

Find Deal

Fri, Dec 12 - Sat, Dec 20

6:50 pm - 3:10 pmMKE-SXM

19h 20m2 stops

4:15 pm - 10:27 amSXM-MKE

19h 12m2 stops

$700American Airlines

Find Deal

Sun, Mar 8 - Sun, Mar 22

6:50 pm - 12:50 pmMKE-SXM

17h 00m1 stop

3:07 pm - 9:49 amSXM-MKE

19h 42m1 stop

$747American Airlines

Find Deal

Sun, Mar 8 - Sun, Mar 22

7:13 pm - 4:11 pmMKE-SXM

18h 58m2 stops

2:51 pm - 10:56 pmSXM-MKE

10h 05m1 stop

$820American Airlines

Find Deal

Fri, Nov 21 - Mon, Nov 24

2:53 pm - 4:11 pmMKE-SXM

23h 18m1 stop

2:51 pm - 10:56 pmSXM-MKE

10h 05m1 stop

$829American Airlines

Find Deal

Fri, Nov 21 - Mon, Nov 24

6:49 pm - 1:55 pmMKE-SXM

17h 06m1 stop

3:20 pm - 10:05 pmSXM-MKE

8h 45m1 stop

$1,520American Airlines

Find Deal

Wed, Jan 7 - Wed, Jan 14

United Airlines flights from Milwaukee to Simpson Bay

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

United Airlines

Oct 31

MKE6:39 pmMilwaukee-Mitchell

19h 18m

1 stop

SXM2:57 pmSimpson Bay Princess Juliana

Nov 4

SXM2:52 pmSimpson Bay Princess Juliana

22h 37m

2 stops

MKE11:29 amMilwaukee-Mitchell

$527

Find similar

United Airlines

Dec 12

MKE3:50 pmMilwaukee-Mitchell

20h 00m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

Dec 20

SXM2:40 pmSimpson Bay Princess Juliana

9h 33m

1 stop

MKE10:13 pmMilwaukee-Mitchell

$637

Find similar

American Airlines flights from Milwaukee to Simpson Bay

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

American Airlines

Dec 12

MKE7:19 pmMilwaukee-Mitchell

17h 49m

1 stop

SXM3:08 pmSimpson Bay Princess Juliana

Dec 20

SXM3:28 pmSimpson Bay Princess Juliana

10h 31m

1 stop

MKE11:59 pmMilwaukee-Mitchell

$655

Find similar

American Airlines

Oct 31

MKE12:20 pmMilwaukee-Mitchell

24h 17m

2 stops

SXM1:37 pmSimpson Bay Princess Juliana

Nov 4

SXM5:24 pmSimpson Bay Princess Juliana

20h 37m

2 stops

MKE12:01 pmMilwaukee-Mitchell

$657

Find similar

American Airlines

Dec 12

MKE5:00 amMilwaukee-Mitchell

9h 25m

2 stops

SXM4:25 pmSimpson Bay Princess Juliana

Dec 20

SXM5:33 pmSimpson Bay Princess Juliana

19h 30m

2 stops

MKE11:03 amMilwaukee-Mitchell

$660

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 10/31

6:39 pm-2:57 pm

1 stop19h 18m

Simpson Bay Princess Juliana

Tue 11/4

2:52 pm-11:29 am

2 stops22h 37m

$527

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 12/12

3:50 pm-1:50 pm

2 stops20h 00m

Simpson Bay Princess Juliana

Sat 12/20

2:40 pm-10:13 pm

1 stop9h 33m

$637

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 12/12

7:19 pm-3:08 pm

1 stop17h 49m

Simpson Bay Princess Juliana

Sat 12/20

3:28 pm-11:59 pm

1 stop10h 31m

$655

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 10/31

12:20 pm-1:37 pm

2 stops24h 17m

Simpson Bay Princess Juliana

Tue 11/4

5:24 pm-12:01 pm

2 stops20h 37m

$657

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 12/12

5:00 am-4:25 pm

2 stops9h 25m

Simpson Bay Princess Juliana

Sat 12/20

5:33 pm-11:03 am

2 stops19h 30m

$660

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 3/8

6:50 pm-3:10 pm

2 stops19h 20m

Simpson Bay Princess Juliana

Sun 3/22

4:15 pm-10:27 am

2 stops19h 12m

$700

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 3/8

6:50 pm-12:50 pm

1 stop17h 00m

Simpson Bay Princess Juliana

Sun 3/22

3:07 pm-9:49 am

1 stop19h 42m

$747

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 11/21

7:13 pm-4:11 pm

2 stops18h 58m

Simpson Bay Princess Juliana

Mon 11/24

2:51 pm-10:56 pm

1 stop10h 05m

$820

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 11/21

2:53 pm-4:11 pm

1 stop23h 18m

Simpson Bay Princess Juliana

Mon 11/24

2:51 pm-10:56 pm

1 stop10h 05m

$829

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 1/7

6:49 pm-1:55 pm

1 stop17h 06m

Simpson Bay Princess Juliana

Wed 1/14

3:20 pm-10:05 pm

1 stop8h 45m

$1,520

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

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $557. Flights from Milwaukee to Simpson Bay on a Monday will generally be more expensive and average around $730. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is in the afternoon. momondo users have found flights departing from Milwaukee to Simpson Bay in the afternoon for as low as $614. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $669.

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

Direct flights	None

There are no direct flights from Milwaukee to Simpson Bay. There are no popular flight routes from Milwaukee to Simpson Bay.

Search flight deals

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 9h 25m.
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 2 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of September 2025.
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 (65% of total bookings). The next most popular airline is American Airlines (35%).

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
Delta	PriceFrom $572	Free Cancellation	Rating 7.9 7,954 reviews		Search Delta flights
American Airlines	PriceFrom $584	Free Cancellation	Rating 7.2 10,000 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

Wed 10/15

Wed 10/22

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

Fly your favorite airline to Simpson Bay

Cheap flights from Milwaukee to Simpson Bay from $527

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 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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

Find the cheapest flights from Milwaukee to Simpson Bay

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

United Airlines flights from Milwaukee to Simpson Bay

Our best United Airlines 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

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

What is the cheapest day to depart on your flight to Simpson Bay?

What is the cheapest time of day to depart on your flight to Simpson Bay?

What airlines fly to Simpson Bay?

When to book flights from Milwaukee to Simpson Bay

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

Direct flights

How far is Milwaukee-Mitchell to Simpson Bay Princess Juliana by plane?

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?

How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport?

How old do you have to be to fly 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?

What is the most popular airline 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?

Why should I use momondo to find a flight deal from Milwaukee to Simpson Bay?

Can I find flights from Milwaukee to Simpson Bay with flexible booking policies on momondo?

How can momondo help me find flights from Milwaukee to Simpson Bay?

I’m not ready to book a flight from Milwaukee to Simpson Bay right now. Can momondo alert me if prices change?

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