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Cheap flights from Milwaukee to Simpson Bay from $498

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 4/7. 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
1 adult, Economy, 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
5:29 pm - 1:20 pm
MKE
-
SXM
18h 51m
2 stops
American Airlines Logo
2:24 pm - 9:57 pm
SXM
-
MKE
8h 33m
1 stop
$498American Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
5:29 pm - 1:21 pm
MKE
-
SXM
18h 52m
1 stop
American Airlines Logo
2:24 pm - 9:57 pm
SXM
-
MKE
8h 33m
1 stop
$502American Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
6:41 pm - 1:11 pm
MKE
-
SXM
17h 30m
1 stop
American Airlines Logo
2:24 pm - 10:57 pm
SXM
-
MKE
9h 33m
1 stop
$518American Airlines
Fri, Apr 24 - Fri, May 1
American Airlines Logo
6:41 pm - 1:20 pm
MKE
-
SXM
17h 39m
2 stops
American Airlines Logo
2:24 pm - 10:43 am
SXM
-
MKE
21h 19m
2 stops
$523American Airlines
Fri, Apr 24 - Tue, Apr 28
American Airlines Logo
6:32 pm - 1:21 pm
MKE
-
SXM
17h 49m
1 stop
American Airlines Logo
2:20 pm - 10:47 pm
SXM
-
MKE
9h 27m
1 stop
$546American Airlines
Sat, May 9 - Sat, May 16
American Airlines Logo
5:41 pm - 1:11 pm
MKE
-
SXM
18h 30m
2 stops
American Airlines Logo
4:35 pm - 10:59 am
SXM
-
MKE
19h 24m
2 stops
$551American Airlines
Fri, Apr 24 - Tue, Apr 28
American Airlines Logo
4:26 pm - 11:37 am
MKE
-
SXM
18h 11m
2 stops
American Airlines Logo
4:35 pm - 11:30 am
SXM
-
MKE
19h 55m
2 stops
$553American Airlines
Fri, Apr 24 - Tue, Apr 28
American Airlines Logo
6:41 pm - 1:11 pm
MKE
-
SXM
17h 30m
1 stop
American Airlines Logo
2:24 pm - 9:57 pm
SXM
-
MKE
8h 33m
1 stop
$594American Airlines
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
5:10 am - 2:00 pm
MKE
-
SXM
7h 50m
1 stop
Southwest Logo
3:00 pm - 10:45 pm
SXM
-
MKE
8h 45m
1 stop
$600Southwest
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
5:00 am - 2:35 pm
MKE
-
SXM
8h 35m
1 stop
Southwest Logo
3:35 pm - 9:50 am
SXM
-
MKE
19h 15m
2 stops
$605Southwest
Sun, Jun 14 - Sun, Jun 21

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Apr 7
MKE5:29 pmMilwaukee-Mitchell
18h 51m
2 stops
SXM1:20 pmSimpson Bay Princess Juliana
Apr 14
SXM2:24 pmSimpson Bay Princess Juliana
8h 33m
1 stop
MKE9:57 pmMilwaukee-Mitchell
$498
American Airlines
Apr 7
MKE5:29 pmMilwaukee-Mitchell
18h 52m
1 stop
SXM1:21 pmSimpson Bay Princess Juliana
Apr 14
SXM2:24 pmSimpson Bay Princess Juliana
8h 33m
1 stop
MKE9:57 pmMilwaukee-Mitchell
$502
American Airlines
Apr 24
MKE6:41 pmMilwaukee-Mitchell
17h 30m
1 stop
SXM1:11 pmSimpson Bay Princess Juliana
May 1
SXM2:24 pmSimpson Bay Princess Juliana
9h 33m
1 stop
MKE10:57 pmMilwaukee-Mitchell
$518

Southwest flights from Milwaukee to Simpson Bay

Our best Southwest deals on Milwaukee to Simpson Bay flight tickets
Southwest
Jul 8
MKE5:10 amMilwaukee-Mitchell
7h 50m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Jul 15
SXM3:00 pmSimpson Bay Princess Juliana
8h 45m
1 stop
MKE10:45 pmMilwaukee-Mitchell
$600
Southwest
Jun 14
MKE5:00 amMilwaukee-Mitchell
8h 35m
1 stop
SXM2:35 pmSimpson Bay Princess Juliana
Jun 21
SXM3:35 pmSimpson Bay Princess Juliana
19h 15m
2 stops
MKE9:50 amMilwaukee-Mitchell
$605
Southwest
Jul 9
MKE5:00 amMilwaukee-Mitchell
8h 00m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Jul 16
SXM3:00 pmSimpson Bay Princess Juliana
10h 05m
1 stop
MKE12:05 amMilwaukee-Mitchell
$625

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 March 12, 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

Tue 4/7

5:29 pm-1:20 pm

2 stops18h 51m

Simpson Bay Princess Juliana

Tue 4/14

2:24 pm-9:57 pm

1 stop8h 33m

$498

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 4/7

5:29 pm-1:21 pm

1 stop18h 52m

Simpson Bay Princess Juliana

Tue 4/14

2:24 pm-9:57 pm

1 stop8h 33m

$502

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:41 pm-1:11 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Fri 5/1

2:24 pm-10:57 pm

1 stop9h 33m

$518

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:41 pm-1:20 pm

2 stops17h 39m

Simpson Bay Princess Juliana

Tue 4/28

2:24 pm-10:43 am

2 stops21h 19m

$523

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 5/9

6:32 pm-1:21 pm

1 stop17h 49m

Simpson Bay Princess Juliana

Sat 5/16

2:20 pm-10:47 pm

1 stop9h 27m

$546

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

5:41 pm-1:11 pm

2 stops18h 30m

Simpson Bay Princess Juliana

Tue 4/28

4:35 pm-10:59 am

2 stops19h 24m

$551

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

4:26 pm-11:37 am

2 stops18h 11m

Simpson Bay Princess Juliana

Tue 4/28

4:35 pm-11:30 am

2 stops19h 55m

$553

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:41 pm-1:11 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Tue 4/28

2:24 pm-9:57 pm

1 stop8h 33m

$594
Quickest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 7/8

5:10 am-2:00 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Wed 7/15

3:00 pm-10:45 pm

1 stop8h 45m

$600

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 6/14

5:00 am-2:35 pm

1 stop8h 35m

Simpson Bay Princess Juliana

Sun 6/21

3:35 pm-9:50 am

2 stops19h 15m

$605

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 airlines fly to Simpson Bay?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Simpson Bay from Milwaukee according to our data. American Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 6 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

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
7.1
11,435 reviews
Search American Airlines flights
DeltaPriceFrom $612Free CancellationRating
7.9
8,286 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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Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo
American Airlines
United Airlines
Spirit Airlines
Delta
JetBlue
Air Canada