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Cheap flights from Milwaukee to Simpson Bay from $197

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 8/13. 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
5:34 am - 1:53 pm
MKE
-
SXM
7h 19m
1 stop
Delta Logo
3:18 pm - 11:53 pm
SXM
-
MKE
9h 35m
1 stop
$483Delta
Thu, Aug 13 - Wed, Aug 19
Delta Logo
4:17 pm - 2:14 pm
MKE
-
SXM
20h 57m
2 stops
Delta Logo
3:18 pm - 11:53 pm
SXM
-
MKE
9h 35m
1 stop
$488Delta
Fri, Aug 14 - Wed, Aug 19
American Airlines Logo
5:50 pm - 3:39 pm
MKE
-
SXM
20h 49m
2 stops
American Airlines Logo
4:39 pm - 11:37 am
SXM
-
MKE
19h 58m
2 stops
$520American Airlines
Sat, Aug 15 - Fri, Aug 21
American Airlines Logo
7:00 am - 1:50 pm
MKE
-
SXM
29h 50m
1 stop
American Airlines Logo
4:43 pm - 7:42 am
SXM
-
MKE
15h 59m
2 stops
$529American Airlines
Sat, Jun 6 - Fri, Jun 12
Delta Logo
5:34 am - 1:53 pm
MKE
-
SXM
7h 19m
1 stop
Delta Logo
3:18 pm - 11:53 pm
SXM
-
MKE
9h 35m
1 stop
$542Delta
Mon, Aug 10 - Fri, Aug 21
Delta Logo
12:51 pm - 2:14 pm
MKE
-
SXM
24h 23m
2 stops
Delta Logo
3:18 pm - 11:53 pm
SXM
-
MKE
9h 35m
1 stop
$547Delta
Fri, Aug 14 - Fri, Aug 21
American Airlines Logo
5:50 pm - 1:42 pm
MKE
-
SXM
18h 52m
2 stops
American Airlines Logo
4:39 pm - 11:37 am
SXM
-
MKE
19h 58m
2 stops
$555American Airlines
Thu, Aug 13 - Wed, Aug 19
American Airlines Logo
1:27 pm - 1:42 pm
MKE
-
SXM
23h 15m
1 stop
American Airlines Logo
4:39 pm - 11:37 am
SXM
-
MKE
19h 58m
2 stops
$564American Airlines
Thu, Aug 13 - Wed, Aug 19
American Airlines Logo
1:27 pm - 1:22 pm
MKE
-
SXM
22h 55m
2 stops
American Airlines Logo
4:39 pm - 7:49 am
SXM
-
MKE
16h 10m
2 stops
$570American Airlines
Sat, Aug 15 - Fri, Aug 21
Southwest Logo
5:00 am - 1:25 pm
MKE
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 9:45 pm
SXM
-
MKE
8h 20m
1 stop
$584Southwest
Mon, Jun 15 - Fri, Jun 19

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Aug 15
MKE5:50 pmMilwaukee-Mitchell
20h 49m
2 stops
SXM3:39 pmSimpson Bay Princess Juliana
Aug 21
SXM4:39 pmSimpson Bay Princess Juliana
19h 58m
2 stops
MKE11:37 amMilwaukee-Mitchell
$520
American Airlines
Jun 6
MKE7:00 amMilwaukee-Mitchell
29h 50m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
Jun 12
SXM4:43 pmSimpson Bay Princess Juliana
15h 59m
2 stops
MKE7:42 amMilwaukee-Mitchell
$529
American Airlines
Aug 13
MKE5:50 pmMilwaukee-Mitchell
18h 52m
2 stops
SXM1:42 pmSimpson Bay Princess Juliana
Aug 19
SXM4:39 pmSimpson Bay Princess Juliana
19h 58m
2 stops
MKE11:37 amMilwaukee-Mitchell
$555

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets
Delta
Aug 13
MKE5:34 amMilwaukee-Mitchell
7h 19m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Aug 19
SXM3:18 pmSimpson Bay Princess Juliana
9h 35m
1 stop
MKE11:53 pmMilwaukee-Mitchell
$483
Delta
Aug 14
MKE4:17 pmMilwaukee-Mitchell
20h 57m
2 stops
SXM2:14 pmSimpson Bay Princess Juliana
Aug 19
SXM3:18 pmSimpson Bay Princess Juliana
9h 35m
1 stop
MKE11:53 pmMilwaukee-Mitchell
$488
Delta
Aug 10
MKE5:34 amMilwaukee-Mitchell
7h 19m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Aug 21
SXM3:18 pmSimpson Bay Princess Juliana
9h 35m
1 stop
MKE11:53 pmMilwaukee-Mitchell
$542

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 May 9, 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

Cheapest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 8/13

5:34 am-1:53 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Wed 8/19

3:18 pm-11:53 pm

1 stop9h 35m

$483

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 8/14

4:17 pm-2:14 pm

2 stops20h 57m

Simpson Bay Princess Juliana

Wed 8/19

3:18 pm-11:53 pm

1 stop9h 35m

$488

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 8/15

5:50 pm-3:39 pm

2 stops20h 49m

Simpson Bay Princess Juliana

Fri 8/21

4:39 pm-11:37 am

2 stops19h 58m

$520

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 6/6

7:00 am-1:50 pm

1 stop29h 50m

Simpson Bay Princess Juliana

Fri 6/12

4:43 pm-7:42 am

2 stops15h 59m

$529

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 8/10

5:34 am-1:53 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Fri 8/21

3:18 pm-11:53 pm

1 stop9h 35m

$542

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 8/14

12:51 pm-2:14 pm

2 stops24h 23m

Simpson Bay Princess Juliana

Fri 8/21

3:18 pm-11:53 pm

1 stop9h 35m

$547

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 8/13

5:50 pm-1:42 pm

2 stops18h 52m

Simpson Bay Princess Juliana

Wed 8/19

4:39 pm-11:37 am

2 stops19h 58m

$555

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 8/13

1:27 pm-1:42 pm

1 stop23h 15m

Simpson Bay Princess Juliana

Wed 8/19

4:39 pm-11:37 am

2 stops19h 58m

$564

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 8/15

1:27 pm-1:22 pm

2 stops22h 55m

Simpson Bay Princess Juliana

Fri 8/21

4:39 pm-7:49 am

2 stops16h 10m

$570
Quickest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 6/15

5:00 am-1:25 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Fri 6/19

2:25 pm-9:45 pm

1 stop8h 20m

$584

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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, April 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 $0. If you aren’t able to travel to Simpson Bay during the month of April, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $603.

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 00m

Direct flights

None
The fastest flight from Milwaukee to Simpson Bay takes 7h 00m
There are no direct flights from Milwaukee to Simpson Bay. There are no popular flight routes from Milwaukee to Simpson Bay.
Search flight deals

Frequently asked questions about flying from Milwaukee to Simpson Bay

  • 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 00m.

  • 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 $445Free CancellationRating
7.9
8,457 reviews
Search Delta flights
American AirlinesPriceFrom $605Free CancellationRating
7.1
11,669 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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