What airlines fly to Simpson Bay?

American Airlines, United Airlines and Spirit Airlines 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 53% 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.

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

American Airlines is the most popular carrier operating from Milwaukee-Mitchell to Simpson Bay Princess Juliana

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 March 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.

$385 Cheap Flights from Milwaukee to Simpson Bay in 2026

Q: What is the typical price of a round-trip flight between Milwaukee and Simpson Bay?

Prices are currently low for flights on this route. Typical prices usually range from $683 to $1,238. The lowest price recently found on this route was $498.

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

Enter your travel dates to find the best prices.

6:41 pm - 1:11 pm

MKE

SXM

17h 30m

1 stop

2:24 pm - 9:57 pm

SXM

MKE

8h 33m

1 stop

$498American Airlines

Fri, Apr 24 - Tue, Apr 28

6:40 pm - 1:20 pm

MKE

SXM

17h 40m

2 stops

2:24 pm - 9:57 pm

SXM

MKE

8h 33m

1 stop

$503American Airlines

Fri, Apr 24 - Tue, Apr 28

6:42 pm - 3:22 pm

MKE

SXM

19h 40m

2 stops

2:21 pm - 7:41 am

SXM

MKE

18h 20m

2 stops

$528American Airlines

Thu, May 14 - Mon, May 18

6:41 pm - 1:21 pm

MKE

SXM

17h 40m

1 stop

2:24 pm - 10:57 pm

SXM

MKE

9h 33m

1 stop

$559American Airlines

Thu, Apr 16 - Thu, Apr 23

6:30 pm - 1:30 pm

MKE

SXM

18h 00m

2 stops

3:20 pm - 11:45 pm

SXM

MKE

9h 25m

1 stop

$564Southwest

Mon, Apr 20 - Sun, Apr 26

6:40 pm - 3:22 pm

MKE

SXM

19h 42m

2 stops

4:35 pm - 1:23 pm

SXM

MKE

21h 48m

2 stops

$569American Airlines

Mon, Apr 20 - Sun, Apr 26

6:41 pm - 1:11 pm

MKE

SXM

17h 30m

1 stop

2:24 pm - 9:57 pm

SXM

MKE

8h 33m

1 stop

$584American Airlines

Fri, Apr 24 - Tue, Apr 28

5:00 am - 2:25 pm

MKE

SXM

8h 25m

1 stop

2:25 pm - 10:50 pm

SXM

MKE

9h 25m

1 stop

$604Southwest

Sun, Apr 19 - Mon, Apr 27

5:40 am - 1:30 pm

MKE

SXM

6h 50m

1 stop

3:35 pm - 11:35 pm

SXM

MKE

9h 00m

1 stop

$625Southwest

Wed, Jun 3 - Sun, Jun 7

5:29 pm - 12:33 pm

MKE

SXM

18h 04m

2 stops

3:50 pm - 9:57 am

SXM

MKE

19h 07m

2 stops

$630United Airlines

Wed, May 27 - Sun, May 31

American Airlines flights from Milwaukee to Simpson Bay

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

American Airlines

Apr 24

MKE6:41 pmMilwaukee-Mitchell

17h 30m

1 stop

SXM1:11 pmSimpson Bay Princess Juliana

Apr 28

SXM2:24 pmSimpson Bay Princess Juliana

8h 33m

1 stop

MKE9:57 pmMilwaukee-Mitchell

$498

American Airlines

Apr 24

MKE5:41 pmMilwaukee-Mitchell

19h 45m

2 stops

SXM2:26 pmSimpson Bay Princess Juliana

Apr 28

SXM4:35 pmSimpson Bay Princess Juliana

19h 55m

2 stops

MKE11:30 amMilwaukee-Mitchell

$503

American Airlines

May 14

MKE6:42 pmMilwaukee-Mitchell

19h 40m

2 stops

SXM3:22 pmSimpson Bay Princess Juliana

May 18

SXM2:21 pmSimpson Bay Princess Juliana

18h 20m

2 stops

MKE7:41 amMilwaukee-Mitchell

$528

United Airlines flights from Milwaukee to Simpson Bay

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

United Airlines

May 27

MKE6:14 amMilwaukee-Mitchell

7h 29m

1 stop

SXM2:43 pmSimpson Bay Princess Juliana

May 31

SXM3:50 pmSimpson Bay Princess Juliana

19h 07m

2 stops

MKE9:57 amMilwaukee-Mitchell

$630

United Airlines

Mar 15

MKE7:18 pmMilwaukee-Mitchell

18h 33m

2 stops

SXM2:51 pmSimpson Bay Princess Juliana

Mar 18

SXM3:55 pmSimpson Bay Princess Juliana

19h 35m

2 stops

MKE10:30 amMilwaukee-Mitchell

$810

United Airlines

Mar 10

MKE2:54 pmMilwaukee-Mitchell

22h 57m

2 stops

SXM2:51 pmSimpson Bay Princess Juliana

Mar 20

SXM1:52 pmSimpson Bay Princess Juliana

21h 38m

2 stops

MKE10:30 amMilwaukee-Mitchell

$854

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:41 pm-1:11 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Tue 4/28

2:24 pm-9:57 pm

1 stop8h 33m

$498

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:40 pm-1:20 pm

2 stops17h 40m

Simpson Bay Princess Juliana

Tue 4/28

2:24 pm-9:57 pm

1 stop8h 33m

$503

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 5/14

6:42 pm-3:22 pm

2 stops19h 40m

Simpson Bay Princess Juliana

Mon 5/18

2:21 pm-7:41 am

2 stops18h 20m

$528

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 4/16

6:41 pm-1:21 pm

1 stop17h 40m

Simpson Bay Princess Juliana

Thu 4/23

2:24 pm-10:57 pm

1 stop9h 33m

$559

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 4/20

6:30 pm-1:30 pm

2 stops18h 00m

Simpson Bay Princess Juliana

Sun 4/26

3:20 pm-11:45 pm

1 stop9h 25m

$564

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 4/20

6:40 pm-3:22 pm

2 stops19h 42m

Simpson Bay Princess Juliana

Sun 4/26

4:35 pm-1:23 pm

2 stops21h 48m

$569

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:41 pm-1:11 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Tue 4/28

2:24 pm-9:57 pm

1 stop8h 33m

$584

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 4/19

5:00 am-2:25 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Mon 4/27

2:25 pm-10:50 pm

1 stop9h 25m

$604

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 6/3

5:40 am-1:30 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sun 6/7

3:35 pm-11:35 pm

1 stop9h 00m

$625

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 5/27

5:29 pm-12:33 pm

2 stops18h 04m

Simpson Bay Princess Juliana

Sun 5/31

3:50 pm-9:57 am

2 stops19h 07m

$630

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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

What is the typical price of a round-trip flight between Milwaukee and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

In general, August 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 $639. If you aren’t able to travel to Simpson Bay during the month of August, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $671.

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 09m
Direct flights	None

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

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 2 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of March 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 (69% of total bookings). The next most popular airline is Delta (31%).

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
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 11,369 reviews		Search American Airlines flights
Delta	PriceFrom $612	Free Cancellation	Rating 7.9 8,237 reviews		Search Delta 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 4/1

Wed 4/8

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 $385

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 3/13. 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

American Airlines flights from Milwaukee to Simpson Bay

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

United Airlines flights from Milwaukee to Simpson Bay

Our best United 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 typical price of a round-trip flight between Milwaukee and 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?

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

Fastest flight time

Direct flights

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