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

Spirit Airlines and Delta 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 49% 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 July 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.

$242 Cheap Flights from Milwaukee to Simpson Bay in 2025

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Find the cheapest flights from Milwaukee to Simpson Bay

Round-trip

One-way

Cheap round-trip flights

5:00 am - 3:09 pmMKE-SXM

9h 09m2 stops

3:25 pm - 10:34 amSXM-MKE

20h 09m2 stops

$578American Airlines

Find Deal

Mon, Aug 18 - Wed, Aug 27

4:37 pm - 2:00 pmMKE-SXM

44h 23m2 stops

3:05 pm - 11:06 pmSXM-MKE

33h 01m2 stops

$580Spirit Airlines

Find Deal

Sat, Aug 9 - Sat, Aug 16

6:30 pm - 12:15 pmMKE-SXM

15h 45m1 stop

1:45 pm - 11:27 pmSXM-MKE

11h 42m1 stop

$587Delta

Find Deal

Sun, Jan 4 - Wed, Jan 14

4:56 pm - 1:30 pmMKE-SXM

19h 34m2 stops

3:25 pm - 1:03 pmSXM-MKE

22h 38m1 stop

$591American Airlines

Find Deal

Mon, Aug 18 - Wed, Aug 27

5:45 am - 2:55 pmMKE-SXM

7h 10m1 stop

4:26 pm - 12:31 pmSXM-MKE

22h 05m2 stops

$592Delta

Find Deal

Tue, Dec 30 - Fri, Jan 9

5:45 am - 2:55 pmMKE-SXM

7h 10m1 stop

5:16 pm - 11:27 pmSXM-MKE

8h 11m1 stop

$612Delta

Find Deal

Wed, Dec 31 - Sat, Jan 10

4:37 pm - 7:30 pmMKE-SXM

25h 53m3 stops

3:05 pm - 4:23 pmSXM-MKE

26h 18m3 stops

$634

Find Deal

Sat, Aug 9 - Sat, Aug 16

6:05 am - 2:43 pmMKE-SXM

7h 38m1 stop

3:55 pm - 10:13 amSXM-MKE

19h 18m2 stops

$762United Airlines

Find Deal

Sat, Aug 23 - Sat, Aug 30

3:53 pm - 1:51 pmMKE-SXM

19h 58m2 stops

2:53 pm - 11:34 amSXM-MKE

22h 41m2 stops

$827United Airlines

Find Deal

Sun, Dec 28 - Thu, Jan 8

6:00 am - 7:50 pmMKE-SXM

36h 50m3 stops

9:17 am - 11:06 pmSXM-MKE

14h 49m3 stops

$995

Find Deal

Mon, Aug 18 - Wed, Aug 27

American Airlines flights from Milwaukee to Simpson Bay

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

American Airlines

Aug 18

MKE5:00 amMilwaukee-Mitchell

9h 09m

2 stops

SXM3:09 pmSimpson Bay Princess Juliana

Aug 27

SXM3:25 pmSimpson Bay Princess Juliana

20h 09m

2 stops

MKE10:34 amMilwaukee-Mitchell

$578

Find similar

American Airlines

Aug 18

MKE4:56 pmMilwaukee-Mitchell

19h 34m

2 stops

SXM1:30 pmSimpson Bay Princess Juliana

Aug 27

SXM3:25 pmSimpson Bay Princess Juliana

22h 38m

1 stop

MKE1:03 pmMilwaukee-Mitchell

$591

Find similar

American Airlines

Aug 9

MKE2:36 pmMilwaukee-Mitchell

21h 49m

1 stop

SXM1:25 pmSimpson Bay Princess Juliana

Aug 16

SXM4:30 pmSimpson Bay Princess Juliana

17h 58m

2 stops

MKE9:28 amMilwaukee-Mitchell

$626

Find similar

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

Delta

Jan 4

MKE6:30 pmMilwaukee-Mitchell

15h 45m

1 stop

SXM12:15 pmSimpson Bay Princess Juliana

Jan 14

SXM1:45 pmSimpson Bay Princess Juliana

11h 42m

1 stop

MKE11:27 pmMilwaukee-Mitchell

$587

Find similar

Delta

Dec 30

MKE5:45 amMilwaukee-Mitchell

7h 10m

1 stop

SXM2:55 pmSimpson Bay Princess Juliana

Jan 9

SXM4:26 pmSimpson Bay Princess Juliana

22h 05m

2 stops

MKE12:31 pmMilwaukee-Mitchell

$592

Find similar

Delta

Dec 31

MKE5:45 amMilwaukee-Mitchell

7h 10m

1 stop

SXM2:55 pmSimpson Bay Princess Juliana

Jan 10

SXM5:16 pmSimpson Bay Princess Juliana

8h 11m

1 stop

MKE11:27 pmMilwaukee-Mitchell

$612

Find similar

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

Best Price Found	$242
Fastest flight time	7h 09m
Direct flights	None
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Milwaukee in the past 72 hours is $242. The best round-trip flight deal from Milwaukee to Simpson Bay found on momondo in the last 72 hours is $578.

The fastest flight from Milwaukee to Simpson Bay takes 7h 09m

There are no direct flights from Milwaukee to Simpson Bay. Popular non-direct route for this connection is Milwaukee-Mitchell Airport - Simpson Bay Princess Juliana Airport.

There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

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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 July 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 $514	Free Cancellation	Rating 8.0 7,951 reviews		Search Delta flights
American Airlines	PriceFrom $534	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

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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

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Cheap flights from Milwaukee to Simpson Bay from $242

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 8/25. 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

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Price Alerts

Price Alerts

Find the cheapest flights from Milwaukee to Simpson Bay

Cheap round-trip flights

Cheap one-way flights

American Airlines flights from Milwaukee to Simpson Bay

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

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets

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

Spirit Airlines and Delta are the most popular carriers operating 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

Best Price Found

Fastest flight time

Direct flights

Airports in Simpson Bay

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