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Cheap flights from Milwaukee to Simpson Bay from $507

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 3/7. 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
6:39 pm - 1:54 pm
MKE
-
SXM
17h 15m
1 stop
Delta Logo
12:55 pm - 8:55 pm
SXM
-
MKE
9h 00m
1 stop
$507Delta
Sat, Mar 7 - Mon, Mar 16
Delta Logo
5:45 am - 1:54 pm
MKE
-
SXM
7h 09m
1 stop
Delta Logo
12:55 pm - 11:58 pm
SXM
-
MKE
12h 03m
1 stop
$515Delta
Sun, Mar 22 - Wed, Mar 25
Delta Logo
5:45 am - 1:54 pm
MKE
-
SXM
7h 09m
1 stop
Delta Logo
3:20 pm - 12:30 pm
SXM
-
MKE
22h 10m
2 stops
$520Delta
Sun, Mar 22 - Wed, Mar 25
KLM Logo
6:39 pm - 1:54 pm
MKE
-
SXM
17h 15m
1 stop
KLM Logo
12:55 pm - 8:55 pm
SXM
-
MKE
9h 00m
1 stop
$540KLM
Sat, Mar 7 - Mon, Mar 16
Delta Logo
4:48 pm - 11:29 am
MKE
-
SXM
17h 41m
2 stops
Delta Logo
3:20 pm - 5:53 pm
SXM
-
MKE
27h 33m
2 stops
$565Delta
Mon, Mar 23 - Wed, Mar 25
Southwest Logo
5:30 am - 1:30 pm
MKE
-
SXM
7h 00m
1 stop
Southwest Logo
2:25 pm - 10:50 pm
SXM
-
MKE
9h 25m
1 stop
$580Southwest
Fri, Apr 17 - Tue, Apr 21
Southwest Logo
12:40 pm - 12:25 pm
MKE
-
SXM
22h 45m
2 stops
Southwest Logo
2:25 pm - 10:50 pm
SXM
-
MKE
9h 25m
1 stop
$585Southwest
Fri, Apr 17 - Tue, Apr 21
United Airlines Logo
7:18 pm - 2:51 pm
MKE
-
SXM
18h 33m
2 stops
United Airlines Logo
3:50 pm - 10:00 am
SXM
-
MKE
19h 10m
2 stops
$610United Airlines
Mon, Mar 23 - Mon, Mar 30
Delta Logo
5:45 am - 1:54 pm
MKE
-
SXM
7h 09m
1 stop
Delta Logo
12:55 pm - 11:58 pm
SXM
-
MKE
12h 03m
1 stop
$623Delta
Sun, Mar 22 - Fri, Mar 27
American Airlines Logo
6:37 pm - 1:16 pm
MKE
-
SXM
17h 39m
1 stop
American Airlines Logo
4:01 pm - 10:01 am
SXM
-
MKE
19h 00m
1 stop
$625American Airlines
Mon, Mar 23 - Mon, Mar 30

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Mar 23
MKE6:37 pmMilwaukee-Mitchell
17h 39m
1 stop
SXM1:16 pmSimpson Bay Princess Juliana
Mar 30
SXM4:01 pmSimpson Bay Princess Juliana
19h 00m
1 stop
MKE10:01 amMilwaukee-Mitchell
$625
American Airlines
Mar 25
MKE6:37 pmMilwaukee-Mitchell
19h 51m
2 stops
SXM3:28 pmSimpson Bay Princess Juliana
Apr 1
SXM4:28 pmSimpson Bay Princess Juliana
19h 33m
2 stops
MKE11:01 amMilwaukee-Mitchell
$630
American Airlines
Jun 22
MKE5:53 pmMilwaukee-Mitchell
20h 49m
2 stops
SXM3:42 pmSimpson Bay Princess Juliana
Jun 28
SXM1:45 pmSimpson Bay Princess Juliana
11h 02m
1 stop
MKE11:47 pmMilwaukee-Mitchell
$635

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets
Delta
Mar 7
MKE6:39 pmMilwaukee-Mitchell
17h 15m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
Mar 16
SXM12:55 pmSimpson Bay Princess Juliana
9h 00m
1 stop
MKE8:55 pmMilwaukee-Mitchell
$507
Delta
Mar 22
MKE5:45 amMilwaukee-Mitchell
7h 09m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
Mar 25
SXM12:55 pmSimpson Bay Princess Juliana
12h 03m
1 stop
MKE11:58 pmMilwaukee-Mitchell
$515
Delta
Mar 22
MKE5:45 amMilwaukee-Mitchell
7h 09m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
Mar 25
SXM3:20 pmSimpson Bay Princess Juliana
22h 10m
2 stops
MKE12:30 pmMilwaukee-Mitchell
$520

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 February 23, 2026.
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 3/7

6:39 pm-1:54 pm

1 stop17h 15m

Simpson Bay Princess Juliana

Mon 3/16

12:55 pm-8:55 pm

1 stop9h 00m

$507

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 3/22

5:45 am-1:54 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Wed 3/25

12:55 pm-11:58 pm

1 stop12h 03m

$515

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 3/22

5:45 am-1:54 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Wed 3/25

3:20 pm-12:30 pm

2 stops22h 10m

$520

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 3/7

6:39 pm-1:54 pm

1 stop17h 15m

Simpson Bay Princess Juliana

Mon 3/16

12:55 pm-8:55 pm

1 stop9h 00m

$540

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 3/23

4:48 pm-11:29 am

2 stops17h 41m

Simpson Bay Princess Juliana

Wed 3/25

3:20 pm-5:53 pm

2 stops27h 33m

$565

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/17

5:30 am-1:30 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Tue 4/21

2:25 pm-10:50 pm

1 stop9h 25m

$580

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/17

12:40 pm-12:25 pm

2 stops22h 45m

Simpson Bay Princess Juliana

Tue 4/21

2:25 pm-10:50 pm

1 stop9h 25m

$585

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 3/23

7:18 pm-2:51 pm

2 stops18h 33m

Simpson Bay Princess Juliana

Mon 3/30

3:50 pm-10:00 am

2 stops19h 10m

$610

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 3/22

5:45 am-1:54 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Fri 3/27

12:55 pm-11:58 pm

1 stop12h 03m

$623

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 3/23

6:37 pm-1:16 pm

1 stop17h 39m

Simpson Bay Princess Juliana

Mon 3/30

4:01 pm-10:01 am

1 stop19h 00m

$625

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, August 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 $639. If you aren’t able to travel to Simpson Bay during the month of August, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $671.

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
American AirlinesPriceFrom $605Free CancellationRating
7.2
11,339 reviews
Search American Airlines flights
DeltaPriceFrom $612Free CancellationRating
7.9
8,236 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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