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

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

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.

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 3 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of May 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.

$483 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 $826 to $794. The lowest price recently found on this route was $483.

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Find the cheapest flights from Milwaukee to Simpson Bay

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5:40 am - 1:53 pm

MKE

SXM

7h 13m

1 stop

3:20 pm - 11:56 pm

SXM

MKE

9h 36m

1 stop

$483Delta

sáb., jul. 4 - jue., jul. 9

6:14 am - 2:43 pm

MKE

SXM

7h 29m

1 stop

3:50 pm - 7:00 am

SXM

MKE

16h 10m

2 stops

$514United Airlines

sáb., jul. 4 - jue., jul. 9

5:34 am - 1:53 pm

MKE

SXM

7h 19m

1 stop

3:18 pm - 11:53 pm

SXM

MKE

9h 35m

1 stop

$524Delta

mié., ago. 12 - mié., ago. 19

5:34 am - 1:53 pm

MKE

SXM

7h 19m

1 stop

3:18 pm - 11:53 pm

SXM

MKE

9h 35m

1 stop

$542Delta

vie., ago. 14 - jue., ago. 20

5:00 am - 3:39 pm

MKE

SXM

9h 39m

2 stops

4:39 pm - 12:47 pm

SXM

MKE

21h 08m

2 stops

$575American Airlines

mié., ago. 12 - mié., ago. 19

5:45 am - 1:49 pm

MKE

SXM

7h 04m

1 stop

3:14 pm - 11:24 pm

SXM

MKE

9h 10m

1 stop

$589Delta

vie., oct. 23 - vie., oct. 30

2:49 pm - 1:22 pm

MKE

SXM

21h 33m

2 stops

4:39 pm - 12:23 pm

SXM

MKE

20h 44m

2 stops

$600American Airlines

lun., ago. 10 - vie., ago. 21

6:00 pm - 12:42 pm

MKE

SXM

17h 42m

1 stop

2:42 pm - 10:59 pm

SXM

MKE

9h 17m

1 stop

$615American Airlines

vie., ago. 14 - vie., ago. 21

3:12 pm - 12:33 pm

MKE

SXM

20h 21m

2 stops

3:50 pm - 7:00 am

SXM

MKE

16h 10m

2 stops

$619United Airlines

mié., jun. 24 - mié., jul. 1

2:49 pm - 1:22 pm

MKE

SXM

21h 33m

2 stops

2:42 pm - 10:59 pm

SXM

MKE

9h 17m

1 stop

$620American Airlines

vie., ago. 14 - vie., ago. 21

United Airlines flights from Milwaukee to Simpson Bay

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

United Airlines

Jul 4

MKE6:14 amMilwaukee-Mitchell

7h 29m

1 stop

SXM2:43 pmSimpson Bay Princess Juliana

Jul 9

SXM3:50 pmSimpson Bay Princess Juliana

16h 10m

2 stops

MKE7:00 amMilwaukee-Mitchell

$514

United Airlines

Jun 24

MKE3:12 pmMilwaukee-Mitchell

20h 21m

2 stops

SXM12:33 pmSimpson Bay Princess Juliana

Jul 1

SXM3:50 pmSimpson Bay Princess Juliana

16h 10m

2 stops

MKE7:00 amMilwaukee-Mitchell

$619

United Airlines

Jul 4

MKE5:00 amMilwaukee-Mitchell

30h 33m

2 stops

SXM12:33 pmSimpson Bay Princess Juliana

Jul 9

SXM3:50 pmSimpson Bay Princess Juliana

28h 36m

2 stops

MKE7:26 pmMilwaukee-Mitchell

$623

American Airlines flights from Milwaukee to Simpson Bay

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

American Airlines

Aug 12

MKE5:00 amMilwaukee-Mitchell

9h 39m

2 stops

SXM3:39 pmSimpson Bay Princess Juliana

Aug 19

SXM4:39 pmSimpson Bay Princess Juliana

21h 08m

2 stops

MKE12:47 pmMilwaukee-Mitchell

$575

American Airlines

Aug 10

MKE2:49 pmMilwaukee-Mitchell

21h 33m

2 stops

SXM1:22 pmSimpson Bay Princess Juliana

Aug 21

SXM4:39 pmSimpson Bay Princess Juliana

20h 44m

2 stops

MKE12:23 pmMilwaukee-Mitchell

$600

American Airlines

Aug 14

MKE6:00 pmMilwaukee-Mitchell

17h 42m

1 stop

SXM12:42 pmSimpson Bay Princess Juliana

Aug 21

SXM2:42 pmSimpson Bay Princess Juliana

9h 17m

1 stop

MKE10:59 pmMilwaukee-Mitchell

$615

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

sáb. 7/4

5:40 am-1:53 pm

1 stop7h 13m

Simpson Bay Princess Juliana

jue. 7/9

3:20 pm-11:56 pm

1 stop9h 36m

$483

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

sáb. 7/4

6:14 am-2:43 pm

1 stop7h 29m

Simpson Bay Princess Juliana

jue. 7/9

3:50 pm-7:00 am

2 stops16h 10m

$514

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

mié. 8/12

5:34 am-1:53 pm

1 stop7h 19m

Simpson Bay Princess Juliana

mié. 8/19

3:18 pm-11:53 pm

1 stop9h 35m

$524

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 8/14

5:34 am-1:53 pm

1 stop7h 19m

Simpson Bay Princess Juliana

jue. 8/20

3:18 pm-11:53 pm

1 stop9h 35m

$542

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

mié. 8/12

5:00 am-3:39 pm

2 stops9h 39m

Simpson Bay Princess Juliana

mié. 8/19

4:39 pm-12:47 pm

2 stops21h 08m

$575

Quickest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 10/23

5:45 am-1:49 pm

1 stop7h 04m

Simpson Bay Princess Juliana

vie. 10/30

3:14 pm-11:24 pm

1 stop9h 10m

$589

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

lun. 8/10

2:49 pm-1:22 pm

2 stops21h 33m

Simpson Bay Princess Juliana

vie. 8/21

4:39 pm-12:23 pm

2 stops20h 44m

$600

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 8/14

6:00 pm-12:42 pm

1 stop17h 42m

Simpson Bay Princess Juliana

vie. 8/21

2:42 pm-10:59 pm

1 stop9h 17m

$615

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

mié. 6/24

3:12 pm-12:33 pm

2 stops20h 21m

Simpson Bay Princess Juliana

mié. 7/1

3:50 pm-7:00 am

2 stops16h 10m

$619

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

vie. 8/14

2:49 pm-1:22 pm

2 stops21h 33m

Simpson Bay Princess Juliana

vie. 8/21

2:42 pm-10:59 pm

1 stop9h 17m

$620

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 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, April 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 April, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $603.

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 13m
Direct flights	None

The fastest flight from Milwaukee to Simpson Bay takes 7h 13m

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 13m.
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 3 operators available for flights from Milwaukee-Mitchell Airport to Simpson Bay Princess Juliana Airport as of May 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 (58% of total bookings). The next most popular airlines are Delta (26%) and United Airlines (16%).

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 9,749 reviews	Search United Airlines flights
Delta	PriceFrom $483	Free Cancellation	Rating 7.9 8,425 reviews	Search Delta flights
American Airlines	PriceFrom $605	Free Cancellation	Rating 7.1 11,629 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 $483

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 7/4. 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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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

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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

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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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