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Cheap flights from Milwaukee to Simpson Bay from $501

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 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Milwaukee to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:30 am - 4:28 pmMKE-SXM
7h 58m1 stop
American Airlines Logo
3:09 pm - 11:23 pmSXM-MKE
10h 14m1 stop
$501American Airlines
Find Deal
Wed, Jan 28 - Wed, Feb 4
American Airlines Logo
6:30 am - 4:28 pmMKE-SXM
7h 58m1 stop
American Airlines Logo
3:31 pm - 9:52 amSXM-MKE
20h 21m2 stops
$506American Airlines
Find Deal
Wed, Jan 28 - Wed, Feb 4
American Airlines Logo
4:05 pm - 3:22 pmMKE-SXM
21h 17m2 stops
American Airlines Logo
5:33 pm - 9:52 amSXM-MKE
18h 19m2 stops
$536American Airlines
Find Deal
Wed, Jan 28 - Wed, Feb 4
Delta Logo
5:30 am - 2:55 pmMKE-SXM
7h 25m1 stop
Delta Logo
1:55 pm - 7:58 pmSXM-MKE
8h 03m1 stop
$577Delta
Find Deal
Sun, Jan 18 - Tue, Jan 27
Delta Logo
5:40 am - 2:50 pmMKE-SXM
7h 10m1 stop
Delta Logo
1:55 pm - 11:28 pmSXM-MKE
11h 33m1 stop
$587Delta
Find Deal
Sun, Jan 4 - Fri, Jan 9
United Airlines Logo
5:00 am - 3:57 pmMKE-SXM
8h 57m1 stop
United Airlines Logo
2:52 pm - 10:34 amSXM-MKE
21h 42m2 stops
$592United Airlines
Find Deal
Sun, Jan 4 - Fri, Jan 9
Delta Logo
5:30 am - 2:55 pmMKE-SXM
7h 25m1 stop
Delta Logo
1:55 pm - 7:58 pmSXM-MKE
8h 03m1 stop
$603Delta
Find Deal
Mon, Jan 19 - Sun, Jan 25
American Airlines Logo
6:38 pm - 2:19 pmMKE-SXM
17h 41m1 stop
American Airlines Logo
1:41 pm - 11:59 pmSXM-MKE
12h 18m1 stop
$605American Airlines
Find Deal
Sun, Feb 15 - Fri, Feb 20
American Airlines Logo
6:38 pm - 2:19 pmMKE-SXM
17h 41m1 stop
American Airlines Logo
3:19 pm - 9:02 amSXM-MKE
19h 43m2 stops
$610American Airlines
Find Deal
Sun, Feb 15 - Fri, Feb 20
Delta Logo
5:40 am - 2:50 pmMKE-SXM
7h 10m1 stop
Delta Logo
5:28 pm - 11:28 pmSXM-MKE
8h 00m1 stop
$612Delta
Find Deal
Sun, Jan 4 - Sat, Jan 10

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Jan 28
MKE6:30 amMilwaukee-Mitchell
7h 58m
1 stop
SXM4:28 pmSimpson Bay Princess Juliana
Feb 4
SXM3:09 pmSimpson Bay Princess Juliana
10h 14m
1 stop
MKE11:23 pmMilwaukee-Mitchell
$501
Find similar
American Airlines
Jan 28
MKE6:30 amMilwaukee-Mitchell
7h 58m
1 stop
SXM4:28 pmSimpson Bay Princess Juliana
Feb 4
SXM3:31 pmSimpson Bay Princess Juliana
20h 21m
2 stops
MKE9:52 amMilwaukee-Mitchell
$506
Find similar
American Airlines
Jan 28
MKE4:05 pmMilwaukee-Mitchell
21h 17m
2 stops
SXM3:22 pmSimpson Bay Princess Juliana
Feb 4
SXM5:33 pmSimpson Bay Princess Juliana
18h 19m
2 stops
MKE9:52 amMilwaukee-Mitchell
$536
Find similar

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets
Delta
Jan 18
MKE5:30 amMilwaukee-Mitchell
7h 25m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
Jan 27
SXM1:55 pmSimpson Bay Princess Juliana
8h 03m
1 stop
MKE7:58 pmMilwaukee-Mitchell
$577
Find similar
Delta
Feb 2
MKE5:30 amMilwaukee-Mitchell
7h 25m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
Feb 5
SXM1:55 pmSimpson Bay Princess Juliana
8h 03m
1 stop
MKE7:58 pmMilwaukee-Mitchell
$587
Find similar
Delta
Feb 2
MKE3:42 pmMilwaukee-Mitchell
18h 48m
2 stops
SXM12:30 pmSimpson Bay Princess Juliana
Feb 5
SXM1:55 pmSimpson Bay Princess Juliana
8h 03m
1 stop
MKE7:58 pmMilwaukee-Mitchell
$592
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Milwaukee to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 21, 2025.
Use the filters below to find and compare flights from Milwaukee to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 1/28

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Wed 2/4

3:09 pm-11:23 pm

1 stop10h 14m

$501

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 1/28

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Wed 2/4

3:31 pm-9:52 am

2 stops20h 21m

$506

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 1/28

4:05 pm-3:22 pm

2 stops21h 17m

Simpson Bay Princess Juliana

Wed 2/4

5:33 pm-9:52 am

2 stops18h 19m

$536

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 1/18

5:30 am-2:55 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Tue 1/27

1:55 pm-7:58 pm

1 stop8h 03m

$577

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 1/4

5:40 am-2:50 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Fri 1/9

1:55 pm-11:28 pm

1 stop11h 33m

$587

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 1/4

5:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Fri 1/9

2:52 pm-10:34 am

2 stops21h 42m

$592

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 1/19

5:30 am-2:55 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Sun 1/25

1:55 pm-7:58 pm

1 stop8h 03m

$603

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/15

6:38 pm-2:19 pm

1 stop17h 41m

Simpson Bay Princess Juliana

Fri 2/20

1:41 pm-11:59 pm

1 stop12h 18m

$605

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/15

6:38 pm-2:19 pm

1 stop17h 41m

Simpson Bay Princess Juliana

Fri 2/20

3:19 pm-9:02 am

2 stops19h 43m

$610

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 1/4

5:40 am-2:50 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Sat 1/10

5:28 pm-11:28 pm

1 stop8h 00m

$612

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 month to fly to Simpson Bay?

In general, September 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 $612. If you aren’t able to travel to Simpson Bay during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $637.

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 7h 08m.

  • 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?

  • 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?

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
DeltaPriceFrom $584Free CancellationRating
7.9
8,002 reviews
Search Delta flights
American AirlinesPriceFrom $605Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
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.

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