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Cheap flights from Milwaukee to Simpson Bay from $303

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 6/27. 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
6:59 pm - 2:17 pm
MKE
-
SXM
17h 18m
1 stop
Delta Logo
1:38 pm - 8:38 pm
SXM
-
MKE
9h 00m
1 stop
$479Delta
Fri, Feb 6 - Thu, Feb 12
American Airlines Logo
3:11 pm - 2:16 pm
MKE
-
SXM
21h 05m
2 stops
American Airlines Logo
5:01 pm - 10:44 am
SXM
-
MKE
19h 43m
2 stops
$602American Airlines
Sat, Feb 28 - Sat, Mar 7
American Airlines Logo
10:26 am - 4:00 pm
MKE
-
SXM
27h 34m
1 stop
American Airlines Logo
5:01 pm - 10:44 am
SXM
-
MKE
19h 43m
2 stops
$611American Airlines
Sat, Feb 28 - Sat, Mar 7
American Airlines Logo
6:38 am - 3:28 pm
MKE
-
SXM
7h 50m
1 stop
American Airlines Logo
4:01 pm - 10:01 am
SXM
-
MKE
19h 00m
1 stop
$615American Airlines
Tue, Mar 10 - Fri, Mar 20
American Airlines Logo
3:06 pm - 11:37 am
MKE
-
SXM
19h 31m
2 stops
American Airlines Logo
4:36 pm - 9:07 am
SXM
-
MKE
17h 31m
2 stops
$620American Airlines
Sat, May 16 - Fri, May 22
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
$633American Airlines
Mon, Mar 16 - Fri, Mar 20
American Airlines Logo
4:47 pm - 1:21 pm
MKE
-
SXM
19h 34m
2 stops
American Airlines Logo
4:01 pm - 10:01 am
SXM
-
MKE
19h 00m
1 stop
$638American Airlines
Mon, Mar 16 - Fri, Mar 20
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
$640American Airlines
Wed, Mar 25 - Wed, Apr 1
American Airlines Logo
3:11 pm - 1:16 pm
MKE
-
SXM
20h 05m
2 stops
American Airlines Logo
12:29 pm - 7:49 am
SXM
-
MKE
20h 20m
2 stops
$645American Airlines
Sat, Mar 7 - Sat, Mar 14
American Airlines Logo
10:26 am - 3:00 pm
MKE
-
SXM
26h 34m
1 stop
American Airlines Logo
12:29 pm - 11:59 pm
SXM
-
MKE
12h 30m
1 stop
$650American Airlines
Sat, Mar 7 - Sat, Mar 14

Air Canada flights from Milwaukee to Simpson Bay

Our best Air Canada deals on Milwaukee to Simpson Bay flight tickets
Air Canada
Feb 22
MKE7:00 amMilwaukee-Mitchell
31h 00m
2 stops
SXM4:00 pmSimpson Bay Princess Juliana
Feb 26
SXM3:40 pmSimpson Bay Princess Juliana
29h 03m
2 stops
MKE6:43 pmMilwaukee-Mitchell
$906
Air Canada
Feb 22
MKE7:00 amMilwaukee-Mitchell
31h 00m
2 stops
SXM4:00 pmSimpson Bay Princess Juliana
Feb 26
SXM3:40 pmSimpson Bay Princess Juliana
32h 48m
2 stops
MKE10:28 pmMilwaukee-Mitchell
$961

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Feb 4
MKE3:53 pmMilwaukee-Mitchell
19h 05m
2 stops
SXM12:58 pmSimpson Bay Princess Juliana
Feb 7
SXM3:23 pmSimpson Bay Princess Juliana
19h 40m
2 stops
MKE9:03 amMilwaukee-Mitchell
$594
American Airlines
Feb 28
MKE3:11 pmMilwaukee-Mitchell
21h 05m
2 stops
SXM2:16 pmSimpson Bay Princess Juliana
Mar 7
SXM5:01 pmSimpson Bay Princess Juliana
19h 43m
2 stops
MKE10:44 amMilwaukee-Mitchell
$602
American Airlines
Feb 28
MKE10:26 amMilwaukee-Mitchell
27h 34m
1 stop
SXM4:00 pmSimpson Bay Princess Juliana
Mar 7
SXM5:01 pmSimpson Bay Princess Juliana
19h 43m
2 stops
MKE10:44 amMilwaukee-Mitchell
$611

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 January 21, 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

Fri 2/6

6:59 pm-2:17 pm

1 stop17h 18m

Simpson Bay Princess Juliana

Thu 2/12

1:38 pm-8:38 pm

1 stop9h 00m

$479

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 2/28

3:11 pm-2:16 pm

2 stops21h 05m

Simpson Bay Princess Juliana

Sat 3/7

5:01 pm-10:44 am

2 stops19h 43m

$602

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 2/28

10:26 am-4:00 pm

1 stop27h 34m

Simpson Bay Princess Juliana

Sat 3/7

5:01 pm-10:44 am

2 stops19h 43m

$611

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 3/10

6:38 am-3:28 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Fri 3/20

4:01 pm-10:01 am

1 stop19h 00m

$615

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 5/16

3:06 pm-11:37 am

2 stops19h 31m

Simpson Bay Princess Juliana

Fri 5/22

4:36 pm-9:07 am

2 stops17h 31m

$620

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 3/16

6:37 pm-1:16 pm

1 stop17h 39m

Simpson Bay Princess Juliana

Fri 3/20

4:01 pm-10:01 am

1 stop19h 00m

$633

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 3/16

4:47 pm-1:21 pm

2 stops19h 34m

Simpson Bay Princess Juliana

Fri 3/20

4:01 pm-10:01 am

1 stop19h 00m

$638

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 3/25

6:37 pm-1:16 pm

1 stop17h 39m

Simpson Bay Princess Juliana

Wed 4/1

4:01 pm-10:01 am

1 stop19h 00m

$640

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 3/7

3:11 pm-1:16 pm

2 stops20h 05m

Simpson Bay Princess Juliana

Sat 3/14

12:29 pm-7:49 am

2 stops20h 20m

$645

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 3/7

10:26 am-3:00 pm

1 stop26h 34m

Simpson Bay Princess Juliana

Sat 3/14

12:29 pm-11:59 pm

1 stop12h 30m

$650

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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, 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 04m

Direct flights

None
The fastest flight from Milwaukee to Simpson Bay takes 7h 04m
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 04m.

  • 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
11,174 reviews
Search American Airlines flights
DeltaPriceFrom $612Free CancellationRating
7.9
8,088 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.

An easier way to manage your Simpson Bay trip

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