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Cheap flights from Milwaukee to Simpson Bay from $514

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 1/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
3:53 pm - 1:45 pm
MKE
-
SXM
19h 52m2 stops
American Airlines Logo
5:33 pm - 11:17 am
SXM
-
MKE
19h 44m2 stops
$514American Airlines
Tue, Jan 27 - Tue, Feb 3
American Airlines Logo
6:12 am - 1:45 pm
MKE
-
SXM
29h 33m1 stop
American Airlines Logo
3:31 pm - 10:49 pm
SXM
-
MKE
9h 18m1 stop
$518American Airlines
Tue, Jan 27 - Tue, Feb 3
American Airlines Logo
4:05 pm - 12:58 pm
MKE
-
SXM
18h 53m2 stops
American Airlines Logo
4:24 pm - 11:01 am
SXM
-
MKE
20h 37m2 stops
$549American Airlines
Sun, Feb 1 - Sun, Feb 8
American Airlines Logo
4:05 pm - 1:42 pm
MKE
-
SXM
19h 37m1 stop
American Airlines Logo
4:24 pm - 11:35 pm
SXM
-
MKE
9h 11m1 stop
$553American Airlines
Sun, Feb 1 - Sun, Feb 8
Delta Logo
6:43 am - 4:03 pm
MKE
-
SXM
7h 20m1 stop
Delta Logo
5:25 pm - 11:47 pm
SXM
-
MKE
8h 22m1 stop
$569Delta
Sat, Feb 7 - Sat, Feb 14
American Airlines Logo
6:01 am - 4:28 pm
MKE
-
SXM
8h 27m1 stop
American Airlines Logo
3:17 pm - 11:14 pm
SXM
-
MKE
9h 57m1 stop
$577American Airlines
Mon, Feb 16 - Mon, Feb 23
American Airlines Logo
3:11 pm - 12:29 pm
MKE
-
SXM
19h 18m2 stops
American Airlines Logo
5:01 pm - 10:01 am
SXM
-
MKE
19h 00m1 stop
$582American Airlines
Mon, Feb 16 - Mon, Feb 23
American Airlines Logo
6:38 am - 3:28 pm
MKE
-
SXM
7h 50m1 stop
American Airlines Logo
4:01 pm - 10:01 am
SXM
-
MKE
19h 00m1 stop
$595American Airlines
Tue, Mar 10 - Fri, Mar 20
American Airlines Logo
3:05 pm - 11:29 am
MKE
-
SXM
19h 24m2 stops
American Airlines Logo
2:17 pm - 10:01 am
SXM
-
MKE
20h 44m2 stops
$600American Airlines
Tue, Mar 10 - Fri, Mar 20
Delta Logo
5:30 am - 2:55 pm
MKE
-
SXM
7h 25m1 stop
Delta Logo
1:55 pm - 11:30 pm
SXM
-
MKE
11h 35m1 stop
$619Delta
Wed, Jan 14 - Sun, Jan 18

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Jan 27
MKE3:53 pmMilwaukee-Mitchell
19h 52m
2 stops
SXM1:45 pmSimpson Bay Princess Juliana
Feb 3
SXM5:33 pmSimpson Bay Princess Juliana
19h 44m
2 stops
MKE11:17 amMilwaukee-Mitchell
$514
American Airlines
Jan 27
MKE6:12 amMilwaukee-Mitchell
29h 33m
1 stop
SXM1:45 pmSimpson Bay Princess Juliana
Feb 3
SXM3:31 pmSimpson Bay Princess Juliana
9h 18m
1 stop
MKE10:49 pmMilwaukee-Mitchell
$518
American Airlines
Feb 1
MKE4:05 pmMilwaukee-Mitchell
18h 53m
2 stops
SXM12:58 pmSimpson Bay Princess Juliana
Feb 8
SXM4:24 pmSimpson Bay Princess Juliana
20h 37m
2 stops
MKE11:01 amMilwaukee-Mitchell
$549

Air Canada flights from Milwaukee to Simpson Bay

Our best Air Canada deals on Milwaukee to Simpson Bay flight tickets
Air Canada
Jan 11
MKE2:32 pmMilwaukee-Mitchell
23h 28m
2 stops
SXM4:00 pmSimpson Bay Princess Juliana
Jan 15
SXM3:40 pmSimpson Bay Princess Juliana
33h 16m
2 stops
MKE10:56 pmMilwaukee-Mitchell
$1,133
Air Canada
Jan 11
MKE3:20 pmMilwaukee-Mitchell
22h 40m
2 stops
SXM4:00 pmSimpson Bay Princess Juliana
Jan 15
SXM3:40 pmSimpson Bay Princess Juliana
33h 16m
2 stops
MKE10:56 pmMilwaukee-Mitchell
$1,156
Air Canada
Jan 14
MKE7:00 amMilwaukee-Mitchell
29h 40m
2 stops
SXM2:40 pmSimpson Bay Princess Juliana
Jan 21
SXM5:00 pmSimpson Bay Princess Juliana
21h 09m
2 stops
MKE12:09 pmMilwaukee-Mitchell
$2,644

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 8, 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

Tue 1/27

3:53 pm-1:45 pm

2 stops19h 52m

Simpson Bay Princess Juliana

Tue 2/3

5:33 pm-11:17 am

2 stops19h 44m

$514

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 1/27

6:12 am-1:45 pm

1 stop29h 33m

Simpson Bay Princess Juliana

Tue 2/3

3:31 pm-10:49 pm

1 stop9h 18m

$518

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/1

4:05 pm-12:58 pm

2 stops18h 53m

Simpson Bay Princess Juliana

Sun 2/8

4:24 pm-11:01 am

2 stops20h 37m

$549

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 2/1

4:05 pm-1:42 pm

1 stop19h 37m

Simpson Bay Princess Juliana

Sun 2/8

4:24 pm-11:35 pm

1 stop9h 11m

$553

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 2/7

6:43 am-4:03 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/14

5:25 pm-11:47 pm

1 stop8h 22m

$569

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 2/16

6:01 am-4:28 pm

1 stop8h 27m

Simpson Bay Princess Juliana

Mon 2/23

3:17 pm-11:14 pm

1 stop9h 57m

$577

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 2/16

3:11 pm-12:29 pm

2 stops19h 18m

Simpson Bay Princess Juliana

Mon 2/23

5:01 pm-10:01 am

1 stop19h 00m

$582

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

$595

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 3/10

3:05 pm-11:29 am

2 stops19h 24m

Simpson Bay Princess Juliana

Fri 3/20

2:17 pm-10:01 am

2 stops20h 44m

$600

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 1/14

5:30 am-2:55 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Sun 1/18

1:55 pm-11:30 pm

1 stop11h 35m

$619

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 typical price of a round-trip flight between Milwaukee and Simpson Bay?

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 $639.

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
DeltaPriceFrom $584Free CancellationRating
7.9
8,025 reviews
Search Delta flights
American AirlinesPriceFrom $587Free CancellationRating
7.2
11,095 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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