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Cheap flights from Milwaukee to Simpson Bay from $363

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.
American Airlines Logo
4:05 pm - 1:45 pm
MKE
-
SXM
19h 40m1 stop
American Airlines Logo
3:31 pm - 10:49 pm
SXM
-
MKE
9h 18m1 stop
$493American Airlines
Mon, Jan 12 - Wed, Jan 21
American Airlines Logo
6:30 am - 4:28 pm
MKE
-
SXM
7h 58m1 stop
American Airlines Logo
3:09 pm - 11:23 pm
SXM
-
MKE
10h 14m1 stop
$501American Airlines
Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
12:51 pm - 1:45 pm
MKE
-
SXM
22h 54m2 stops
American Airlines Logo
3:09 pm - 11:23 pm
SXM
-
MKE
10h 14m1 stop
$506American Airlines
Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
5:46 pm - 4:27 pm
MKE
-
SXM
20h 41m2 stops
American Airlines Logo
5:28 pm - 11:37 am
SXM
-
MKE
20h 09m2 stops
$566American Airlines
Wed, Feb 25 - Sat, Feb 28
American Airlines Logo
6:38 pm - 2:30 pm
MKE
-
SXM
17h 52m1 stop
American Airlines Logo
1:41 pm - 11:54 pm
SXM
-
MKE
12h 13m1 stop
$574American Airlines
Fri, Feb 27 - Fri, Mar 6
American Airlines Logo
10:30 am - 3:15 pm
MKE
-
SXM
26h 45m1 stop
American Airlines Logo
5:28 pm - 11:37 am
SXM
-
MKE
20h 09m2 stops
$576American Airlines
Wed, Feb 25 - Sat, Feb 28
Delta Logo
5:33 pm - 12:30 pm
MKE
-
SXM
16h 57m2 stops
Delta Logo
1:55 pm - 7:57 pm
SXM
-
MKE
8h 02m1 stop
$578Delta
Mon, Jan 12 - Wed, Jan 21
American Airlines Logo
6:40 am - 4:27 pm
MKE
-
SXM
7h 47m1 stop
American Airlines Logo
5:28 pm - 10:59 am
SXM
-
MKE
19h 31m2 stops
$579American Airlines
Tue, Feb 24 - Sun, Mar 1
American Airlines Logo
6:40 am - 4:27 pm
MKE
-
SXM
7h 47m1 stop
American Airlines Logo
4:05 pm - 10:05 am
SXM
-
MKE
20h 00m1 stop
$585American Airlines
Tue, Feb 24 - Sun, Mar 1
American Airlines Logo
6:40 am - 3:28 pm
MKE
-
SXM
7h 48m1 stop
American Airlines Logo
4:01 pm - 9:56 am
SXM
-
MKE
18h 55m1 stop
$587American Airlines
Tue, Mar 10 - Fri, Mar 20

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Jan 12
MKE4:05 pmMilwaukee-Mitchell
19h 40m
1 stop
SXM1:45 pmSimpson Bay Princess Juliana
Jan 21
SXM3:31 pmSimpson Bay Princess Juliana
9h 18m
1 stop
MKE10:49 pmMilwaukee-Mitchell
$493
Find similar
American Airlines
Feb 3
MKE6:30 amMilwaukee-Mitchell
7h 58m
1 stop
SXM4:28 pmSimpson Bay Princess Juliana
Feb 10
SXM3:09 pmSimpson Bay Princess Juliana
10h 14m
1 stop
MKE11:23 pmMilwaukee-Mitchell
$501
Find similar
American Airlines
Feb 3
MKE12:51 pmMilwaukee-Mitchell
22h 54m
2 stops
SXM1:45 pmSimpson Bay Princess Juliana
Feb 10
SXM3:09 pmSimpson Bay Princess Juliana
10h 14m
1 stop
MKE11:23 pmMilwaukee-Mitchell
$506
Find similar

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets
Delta
Jan 12
MKE5:33 pmMilwaukee-Mitchell
16h 57m
2 stops
SXM12:30 pmSimpson Bay Princess Juliana
Jan 21
SXM1:55 pmSimpson Bay Princess Juliana
8h 02m
1 stop
MKE7:57 pmMilwaukee-Mitchell
$578
Find similar
Delta
Feb 22
MKE1:21 pmMilwaukee-Mitchell
20h 52m
2 stops
SXM12:13 pmSimpson Bay Princess Juliana
Mar 4
SXM4:15 pmSimpson Bay Princess Juliana
22h 19m
2 stops
MKE12:34 pmMilwaukee-Mitchell
$592
Find similar
Delta
Feb 27
MKE5:23 amMilwaukee-Mitchell
7h 27m
1 stop
SXM2:50 pmSimpson Bay Princess Juliana
Mar 3
SXM4:15 pmSimpson Bay Princess Juliana
22h 19m
2 stops
MKE12:34 pmMilwaukee-Mitchell
$617
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 December 22, 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 1/12

4:05 pm-1:45 pm

1 stop19h 40m

Simpson Bay Princess Juliana

Wed 1/21

3:31 pm-10:49 pm

1 stop9h 18m

$493

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/3

6:30 am-4:28 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Tue 2/10

3:09 pm-11:23 pm

1 stop10h 14m

$501

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/3

12:51 pm-1:45 pm

2 stops22h 54m

Simpson Bay Princess Juliana

Tue 2/10

3:09 pm-11:23 pm

1 stop10h 14m

$506

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 2/25

5:46 pm-4:27 pm

2 stops20h 41m

Simpson Bay Princess Juliana

Sat 2/28

5:28 pm-11:37 am

2 stops20h 09m

$566

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 2/27

6:38 pm-2:30 pm

1 stop17h 52m

Simpson Bay Princess Juliana

Fri 3/6

1:41 pm-11:54 pm

1 stop12h 13m

$574

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-11:37 am

2 stops20h 09m

$576

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 1/12

5:33 pm-12:30 pm

2 stops16h 57m

Simpson Bay Princess Juliana

Wed 1/21

1:55 pm-7:57 pm

1 stop8h 02m

$578

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/24

6:40 am-4:27 pm

1 stop7h 47m

Simpson Bay Princess Juliana

Sun 3/1

5:28 pm-10:59 am

2 stops19h 31m

$579

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 2/24

6:40 am-4:27 pm

1 stop7h 47m

Simpson Bay Princess Juliana

Sun 3/1

4:05 pm-10:05 am

1 stop20h 00m

$585

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 3/10

6:40 am-3:28 pm

1 stop7h 48m

Simpson Bay Princess Juliana

Fri 3/20

4:01 pm-9:56 am

1 stop18h 55m

$587

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 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 09m

Direct flights

None
The fastest flight from Milwaukee to Simpson Bay takes 7h 09m
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 09m.

  • 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
8,014 reviews
Search Delta flights
American AirlinesPriceFrom $587Free CancellationRating
7.2
11,052 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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