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Cheap flights from Milwaukee to Simpson Bay from $249

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 12/8. 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
6:46 pm - 2:00 pmMKE-SXM
17h 14m1 stop
American Airlines Logo
4:00 pm - 8:17 amSXM-MKE
18h 17m1 stop
$612American Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
6:50 pm - 1:52 pmMKE-SXM
17h 02m1 stop
American Airlines Logo
5:25 pm - 12:04 pmSXM-MKE
20h 39m2 stops
$617American Airlines
Find Deal
Thu, Dec 11 - Tue, Dec 16
American Airlines Logo
3:52 pm - 1:58 pmMKE-SXM
20h 06m2 stops
American Airlines Logo
5:33 pm - 11:03 amSXM-MKE
19h 30m2 stops
$622American Airlines
Find Deal
Sat, Dec 13 - Sun, Dec 21
American Airlines Logo
3:53 pm - 1:45 pmMKE-SXM
19h 52m2 stops
American Airlines Logo
2:50 pm - 3:04 pmSXM-MKE
26h 14m1 stop
$632American Airlines
Find Deal
Sun, Feb 1 - Sun, Feb 8
Delta Logo
5:45 am - 2:56 pmMKE-SXM
7h 11m1 stop
Delta Logo
1:45 pm - 11:27 pmSXM-MKE
11h 42m1 stop
$651Delta
Find Deal
Sun, Feb 1 - Sun, Feb 8
American Airlines Logo
6:50 pm - 1:50 pmMKE-SXM
17h 00m1 stop
American Airlines Logo
4:15 pm - 11:26 amSXM-MKE
21h 11m2 stops
$661American Airlines
Find Deal
Tue, Feb 24 - Sun, Mar 1
United Airlines Logo
5:00 am - 3:57 pmMKE-SXM
8h 57m1 stop
United Airlines Logo
2:20 pm - 10:30 pmSXM-MKE
10h 10m1 stop
$667United Airlines
Find Deal
Sat, Dec 6 - Sun, Dec 14
Delta Logo
5:45 am - 1:53 pmMKE-SXM
7h 08m1 stop
Delta Logo
12:45 pm - 11:27 pmSXM-MKE
11h 42m1 stop
$736Delta
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Wed, Mar 25 - Thu, Apr 2
Multiple Airlines Logo
1:56 pm - 3:10 pmMKE-SXM
23h 14m3 stops
Multiple Airlines Logo
1:45 pm - 12:51 pmSXM-MKE
25h 06m3 stops
$765Multiple Airlines
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Sun, Feb 1 - Sun, Feb 8
Multiple Airlines Logo
1:56 pm - 3:10 pmMKE-SXM
23h 14m3 stops
Multiple Airlines Logo
1:45 pm - 12:36 pmSXM-MKE
24h 51m3 stops
$879Multiple Airlines
Find Deal
Thu, Feb 5 - Sun, Feb 15

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Nov 29
MKE6:46 pmMilwaukee-Mitchell
17h 14m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Dec 6
SXM4:00 pmSimpson Bay Princess Juliana
18h 17m
1 stop
MKE8:17 amMilwaukee-Mitchell
$612
Find similar
American Airlines
Dec 11
MKE6:50 pmMilwaukee-Mitchell
17h 02m
1 stop
SXM1:52 pmSimpson Bay Princess Juliana
Dec 16
SXM5:25 pmSimpson Bay Princess Juliana
20h 39m
2 stops
MKE12:04 pmMilwaukee-Mitchell
$617
Find similar
American Airlines
Dec 13
MKE3:52 pmMilwaukee-Mitchell
20h 06m
2 stops
SXM1:58 pmSimpson Bay Princess Juliana
Dec 21
SXM5:33 pmSimpson Bay Princess Juliana
19h 30m
2 stops
MKE11:03 amMilwaukee-Mitchell
$622
Find similar

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets
Delta
Feb 1
MKE5:45 amMilwaukee-Mitchell
7h 11m
1 stop
SXM2:56 pmSimpson Bay Princess Juliana
Feb 8
SXM1:45 pmSimpson Bay Princess Juliana
11h 42m
1 stop
MKE11:27 pmMilwaukee-Mitchell
$651
Find similar
Delta
Mar 25
MKE5:45 amMilwaukee-Mitchell
7h 08m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Apr 2
SXM12:45 pmSimpson Bay Princess Juliana
11h 42m
1 stop
MKE11:27 pmMilwaukee-Mitchell
$736
Find similar
Delta
Mar 25
MKE5:45 amMilwaukee-Mitchell
7h 08m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Apr 2
SXM12:45 pmSimpson Bay Princess Juliana
11h 42m
1 stop
MKE11:27 pmMilwaukee-Mitchell
$782
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 October 16, 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

Sat 11/29

6:46 pm-2:00 pm

1 stop17h 14m

Simpson Bay Princess Juliana

Sat 12/6

4:00 pm-8:17 am

1 stop18h 17m

$612

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 12/11

6:50 pm-1:52 pm

1 stop17h 02m

Simpson Bay Princess Juliana

Tue 12/16

5:25 pm-12:04 pm

2 stops20h 39m

$617

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 12/13

3:52 pm-1:58 pm

2 stops20h 06m

Simpson Bay Princess Juliana

Sun 12/21

5:33 pm-11:03 am

2 stops19h 30m

$622

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/1

3:53 pm-1:45 pm

2 stops19h 52m

Simpson Bay Princess Juliana

Sun 2/8

2:50 pm-3:04 pm

1 stop26h 14m

$632

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/1

5:45 am-2:56 pm

1 stop7h 11m

Simpson Bay Princess Juliana

Sun 2/8

1:45 pm-11:27 pm

1 stop11h 42m

$651

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/24

6:50 pm-1:50 pm

1 stop17h 00m

Simpson Bay Princess Juliana

Sun 3/1

4:15 pm-11:26 am

2 stops21h 11m

$661

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 12/6

5:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Sun 12/14

2:20 pm-10:30 pm

1 stop10h 10m

$667

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 3/25

5:45 am-1:53 pm

1 stop7h 08m

Simpson Bay Princess Juliana

Thu 4/2

12:45 pm-11:27 pm

1 stop11h 42m

$736

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/1

1:56 pm-3:10 pm

3 stops23h 14m

Simpson Bay Princess Juliana

Sun 2/8

1:45 pm-12:51 pm

3 stops25h 06m

$765

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 2/5

1:56 pm-3:10 pm

3 stops23h 14m

Simpson Bay Princess Juliana

Sun 2/15

1:45 pm-12:36 pm

3 stops24h 51m

$879

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 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.
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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 6h 43m.

  • 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
American AirlinesPriceFrom $584Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
DeltaPriceFrom $584Free CancellationRating
7.9
7,984 reviews
Search Delta 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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