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Cheap flights from Milwaukee to Simpson Bay from $612

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 12/11. 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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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
5:45 am - 2:28 pmMKE-SXM
6h 43m1 stop
Delta Logo
3:53 pm - 11:54 pmSXM-MKE
10h 01m1 stop
$612Delta
Find Deal
Thu, Dec 11 - Tue, Dec 16
American Airlines Logo
6:30 am - 4:28 pmMKE-SXM
7h 58m1 stop
American Airlines Logo
3:50 pm - 9:52 amSXM-MKE
20h 02m1 stop
$615American Airlines
Find Deal
Tue, Jan 6 - Sun, Jan 11
United Airlines Logo
2:32 pm - 1:50 pmMKE-SXM
21h 18m2 stops
United Airlines Logo
2:52 pm - 10:34 amSXM-MKE
21h 42m2 stops
$617United Airlines
Find Deal
Fri, Jan 9 - Fri, Jan 23
American Airlines Logo
3:53 pm - 2:31 pmMKE-SXM
20h 38m2 stops
American Airlines Logo
5:33 pm - 12:21 pmSXM-MKE
20h 48m2 stops
$619American Airlines
Find Deal
Tue, Jan 6 - Sun, Jan 11
American Airlines Logo
12:11 pm - 12:40 pmMKE-SXM
22h 29m2 stops
American Airlines Logo
5:33 pm - 11:41 amSXM-MKE
20h 08m2 stops
$622American Airlines
Find Deal
Tue, Feb 24 - Sun, Mar 1
Delta Logo
5:30 am - 3:57 pmMKE-SXM
8h 27m1 stop
Delta Logo
1:55 pm - 7:58 pmSXM-MKE
8h 03m1 stop
$637Delta
Find Deal
Sat, Jan 3 - Sat, Jan 10
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
$656American Airlines
Find Deal
Thu, Dec 11 - Tue, Dec 16
Spirit Airlines Logo
8:15 pm - 2:15 pmMKE-SXM
16h 00m2 stops
Spirit Airlines Logo
3:20 pm - 7:20 pmSXM-MKE
30h 00m3 stops
$758Spirit Airlines
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Fri, Dec 19 - Fri, Dec 26
Spirit Airlines Logo
8:15 pm - 2:15 pmMKE-SXM
40h 00m3 stops
Spirit Airlines Logo
3:20 pm - 7:20 pmSXM-MKE
30h 00m3 stops
$1,193Spirit Airlines
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Mon, Dec 29 - Sat, Jan 3
United Airlines Logo
5:00 am - 3:57 pmMKE-SXM
8h 57m1 stop
United Airlines Logo
2:40 pm - 9:59 pmSXM-MKE
9h 19m1 stop
$1,805United Airlines
Find Deal
Sun, Jan 4 - Sat, Jan 10

United Airlines flights from Milwaukee to Simpson Bay

Our best United Airlines deals on Milwaukee to Simpson Bay flight tickets
United Airlines
Jan 9
MKE2:32 pmMilwaukee-Mitchell
21h 18m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Jan 23
SXM2:52 pmSimpson Bay Princess Juliana
21h 42m
2 stops
MKE10:34 amMilwaukee-Mitchell
$617
Find similar
United Airlines
Jan 4
MKE5:00 amMilwaukee-Mitchell
8h 57m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
Jan 10
SXM2:40 pmSimpson Bay Princess Juliana
9h 19m
1 stop
MKE9:59 pmMilwaukee-Mitchell
$1,805
Find similar
United Airlines
Jan 3
MKE6:36 amMilwaukee-Mitchell
7h 21m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
Jan 10
SXM2:40 pmSimpson Bay Princess Juliana
9h 19m
1 stop
MKE9:59 pmMilwaukee-Mitchell
$1,815
Find similar

Spirit Airlines flights from Milwaukee to Simpson Bay

Our best Spirit Airlines deals on Milwaukee to Simpson Bay flight tickets
Spirit Airlines
Dec 19
MKE8:15 pmMilwaukee-Mitchell
16h 00m
2 stops
SXM2:15 pmSimpson Bay Princess Juliana
Dec 26
SXM3:20 pmSimpson Bay Princess Juliana
30h 00m
3 stops
MKE7:20 pmMilwaukee-Mitchell
$758
Find similar
Spirit Airlines
Dec 29
MKE8:15 pmMilwaukee-Mitchell
40h 00m
3 stops
SXM2:15 pmSimpson Bay Princess Juliana
Jan 3
SXM3:20 pmSimpson Bay Princess Juliana
30h 00m
3 stops
MKE7:20 pmMilwaukee-Mitchell
$1,193
Find similar
Spirit Airlines
Dec 29
MKE8:15 pmMilwaukee-Mitchell
40h 00m
3 stops
SXM2:15 pmSimpson Bay Princess Juliana
Jan 3
SXM3:20 pmSimpson Bay Princess Juliana
30h 00m
3 stops
MKE7:20 pmMilwaukee-Mitchell
$1,275
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 6, 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

Thu 12/11

5:45 am-2:28 pm

1 stop6h 43m

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-11:54 pm

1 stop10h 01m

$612

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 1/6

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Sun 1/11

3:50 pm-9:52 am

1 stop20h 02m

$615

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 1/9

2:32 pm-1:50 pm

2 stops21h 18m

Simpson Bay Princess Juliana

Fri 1/23

2:52 pm-10:34 am

2 stops21h 42m

$617

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 1/6

3:53 pm-2:31 pm

2 stops20h 38m

Simpson Bay Princess Juliana

Sun 1/11

5:33 pm-12:21 pm

2 stops20h 48m

$619

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/24

12:11 pm-12:40 pm

2 stops22h 29m

Simpson Bay Princess Juliana

Sun 3/1

5:33 pm-11:41 am

2 stops20h 08m

$622

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 1/3

5:30 am-3:57 pm

1 stop8h 27m

Simpson Bay Princess Juliana

Sat 1/10

1:55 pm-7:58 pm

1 stop8h 03m

$637

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

$656

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 12/19

8:15 pm-2:15 pm

2 stops16h 00m

Simpson Bay Princess Juliana

Fri 12/26

3:20 pm-7:20 pm

3 stops30h 00m

$758

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 12/29

8:15 pm-2:15 pm

3 stops40h 00m

Simpson Bay Princess Juliana

Sat 1/3

3:20 pm-7:20 pm

3 stops30h 00m

$1,193

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 1/4

5:00 am-3:57 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Sat 1/10

2:40 pm-9:59 pm

1 stop9h 19m

$1,805

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 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
DeltaPriceFrom $584Free CancellationRating
7.9
8,001 reviews
Search Delta flights
American AirlinesPriceFrom $605Free CancellationRating
7.2
11,040 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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