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Cheap flights from Milwaukee to Simpson Bay from $278

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 1/9. 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.
Delta Logo
5:30 am - 2:55 pmMKE-SXM
7h 25m1 stop
Delta Logo
1:55 pm - 11:44 pmSXM-MKE
11h 49m1 stop
$501Delta
Find Deal
Mon, Feb 2 - Thu, Feb 5
Delta Logo
7:00 am - 12:30 pmMKE-SXM
27h 30m2 stops
Delta Logo
1:55 pm - 11:44 pmSXM-MKE
11h 49m1 stop
$506Delta
Find Deal
Mon, Feb 2 - Thu, Feb 5
American Airlines Logo
6:30 am - 4:28 pmMKE-SXM
7h 58m1 stop
American Airlines Logo
3:31 pm - 10:58 pmSXM-MKE
9h 27m1 stop
$531American Airlines
Find Deal
Thu, Jan 22 - Wed, Jan 28
American Airlines Logo
3:53 pm - 1:42 pmMKE-SXM
19h 49m2 stops
American Airlines Logo
3:31 pm - 9:52 amSXM-MKE
20h 21m2 stops
$536American Airlines
Find Deal
Thu, Jan 22 - Wed, Jan 28
American Airlines Logo
6:40 am - 4:28 pmMKE-SXM
7h 48m1 stop
American Airlines Logo
4:05 pm - 10:05 amSXM-MKE
20h 00m1 stop
$546American Airlines
Find Deal
Tue, Feb 24 - Sun, Mar 1
Delta Logo
1:21 pm - 12:13 pmMKE-SXM
20h 52m2 stops
Delta Logo
4:15 pm - 2:30 pmSXM-MKE
24h 15m2 stops
$549Delta
Find Deal
Sun, Feb 22 - Fri, Feb 27
American Airlines Logo
5:46 pm - 4:28 pmMKE-SXM
20h 42m2 stops
American Airlines Logo
4:05 pm - 10:05 amSXM-MKE
20h 00m1 stop
$551American Airlines
Find Deal
Tue, Feb 24 - Sun, Mar 1
American Airlines Logo
6:58 pm - 3:07 pmMKE-SXM
18h 09m1 stop
American Airlines Logo
4:24 pm - 11:35 pmSXM-MKE
9h 11m1 stop
$561American Airlines
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Fri, Jan 30 - Mon, Feb 2
American Airlines Logo
5:46 pm - 12:38 pmMKE-SXM
16h 52m2 stops
American Airlines Logo
5:28 pm - 11:37 amSXM-MKE
20h 09m2 stops
$566American Airlines
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Wed, Feb 25 - Sat, Feb 28
American Airlines Logo
10:30 am - 3:15 pmMKE-SXM
26h 45m1 stop
American Airlines Logo
5:28 pm - 10:59 amSXM-MKE
19h 31m2 stops
$576American Airlines
Find Deal
Wed, Feb 25 - Sat, Feb 28

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Jan 22
MKE6:30 amMilwaukee-Mitchell
7h 58m
1 stop
SXM4:28 pmSimpson Bay Princess Juliana
Jan 28
SXM3:31 pmSimpson Bay Princess Juliana
9h 27m
1 stop
MKE10:58 pmMilwaukee-Mitchell
$531
Find similar
American Airlines
Jan 22
MKE3:53 pmMilwaukee-Mitchell
19h 49m
2 stops
SXM1:42 pmSimpson Bay Princess Juliana
Jan 28
SXM3:31 pmSimpson Bay Princess Juliana
20h 21m
2 stops
MKE9:52 amMilwaukee-Mitchell
$536
Find similar
American Airlines
Feb 24
MKE6:40 amMilwaukee-Mitchell
7h 48m
1 stop
SXM4:28 pmSimpson Bay Princess Juliana
Mar 1
SXM4:05 pmSimpson Bay Princess Juliana
20h 00m
1 stop
MKE10:05 amMilwaukee-Mitchell
$546
Find similar

United Airlines flights from Milwaukee to Simpson Bay

Our best United Airlines deals on Milwaukee to Simpson Bay flight tickets
United Airlines
Feb 22
MKE6:00 amMilwaukee-Mitchell
7h 51m
1 stop
SXM3:51 pmSimpson Bay Princess Juliana
Mar 1
SXM4:55 pmSimpson Bay Princess Juliana
31h 33m
2 stops
MKE10:28 pmMilwaukee-Mitchell
$662
Find similar
United Airlines
Feb 22
MKE6:00 amMilwaukee-Mitchell
7h 51m
1 stop
SXM3:51 pmSimpson Bay Princess Juliana
Feb 26
SXM2:52 pmSimpson Bay Princess Juliana
9h 21m
1 stop
MKE10:13 pmMilwaukee-Mitchell
$723
Find similar
United Airlines
Mar 25
MKE3:24 pmMilwaukee-Mitchell
22h 27m
2 stops
SXM2:51 pmSimpson Bay Princess Juliana
Apr 2
SXM3:50 pmSimpson Bay Princess Juliana
23h 17m
2 stops
MKE2:07 pmMilwaukee-Mitchell
$747
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 26, 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

Mon 2/2

5:30 am-2:55 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 2/5

1:55 pm-11:44 pm

1 stop11h 49m

$501

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 2/2

7:00 am-12:30 pm

2 stops27h 30m

Simpson Bay Princess Juliana

Thu 2/5

1:55 pm-11:44 pm

1 stop11h 49m

$506

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 1/22

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Wed 1/28

3:31 pm-10:58 pm

1 stop9h 27m

$531

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 1/22

3:53 pm-1:42 pm

2 stops19h 49m

Simpson Bay Princess Juliana

Wed 1/28

3:31 pm-9:52 am

2 stops20h 21m

$536

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/24

6:40 am-4:28 pm

1 stop7h 48m

Simpson Bay Princess Juliana

Sun 3/1

4:05 pm-10:05 am

1 stop20h 00m

$546

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/22

1:21 pm-12:13 pm

2 stops20h 52m

Simpson Bay Princess Juliana

Fri 2/27

4:15 pm-2:30 pm

2 stops24h 15m

$549

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/24

5:46 pm-4:28 pm

2 stops20h 42m

Simpson Bay Princess Juliana

Sun 3/1

4:05 pm-10:05 am

1 stop20h 00m

$551

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 1/30

6:58 pm-3:07 pm

1 stop18h 09m

Simpson Bay Princess Juliana

Mon 2/2

4:24 pm-11:35 pm

1 stop9h 11m

$561

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 2/25

5:46 pm-12:38 pm

2 stops16h 52m

Simpson Bay Princess Juliana

Sat 2/28

5:28 pm-11:37 am

2 stops20h 09m

$566

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 2/25

10:30 am-3:15 pm

1 stop26h 45m

Simpson Bay Princess Juliana

Sat 2/28

5:28 pm-10:59 am

2 stops19h 31m

$576

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Milwaukee and Simpson Bay?

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

Fastest flight time

7h 23m

Direct flights

None
The fastest flight from Milwaukee to Simpson Bay takes 7h 23m
There are no direct flights from Milwaukee to Simpson Bay. There are no popular flight routes from Milwaukee to Simpson Bay.
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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 23m.

  • 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
7,999 reviews
Search Delta flights
American AirlinesPriceFrom $605Free CancellationRating
7.2
11,038 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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