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Cheap flights from Milwaukee to Simpson Bay from $493

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 10/1. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Milwaukee to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:30 am - 1:50 pm
MKE
-
SXM
7h 20m
1 stop
Delta Logo
3:20 pm - 11:52 pm
SXM
-
MKE
9h 32m
1 stop
$493Delta
Thu, Oct 1 - Sun, Oct 4
American Airlines Logo
5:51 pm - 3:05 pm
MKE
-
SXM
20h 14m
2 stops
American Airlines Logo
5:24 pm - 11:40 am
SXM
-
MKE
20h 16m
2 stops
$538American Airlines
Sat, Oct 24 - Sat, Nov 7
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
$547Delta
Mon, Aug 10 - Fri, Aug 21
American Airlines Logo
4:49 pm - 3:05 pm
MKE
-
SXM
21h 16m
2 stops
American Airlines Logo
2:15 pm - 9:38 am
SXM
-
MKE
21h 23m
1 stop
$548American Airlines
Sat, Oct 24 - Sat, Nov 7
United Airlines Logo
7:23 pm - 12:33 pm
MKE
-
SXM
16h 10m
2 stops
United Airlines Logo
3:50 pm - 9:53 am
SXM
-
MKE
19h 03m
2 stops
$564United Airlines
Sat, Jul 18 - Sat, Jul 25
American Airlines Logo
6:00 pm - 3:39 pm
MKE
-
SXM
20h 39m
2 stops
American Airlines Logo
2:42 pm - 10:59 pm
SXM
-
MKE
9h 17m
1 stop
$570American Airlines
Mon, Aug 10 - Fri, Aug 21
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
$598Delta
Mon, Aug 10 - Fri, Aug 21
American Airlines Logo
6:48 pm - 4:20 pm
MKE
-
SXM
19h 32m
2 stops
American Airlines Logo
2:51 pm - 9:38 am
SXM
-
MKE
20h 47m
2 stops
$605American Airlines
Wed, Nov 11 - Tue, Nov 17
Southwest Logo
8:00 pm - 2:00 pm
MKE
-
SXM
17h 00m
2 stops
Southwest Logo
3:00 pm - 11:35 pm
SXM
-
MKE
9h 35m
1 stop
$616Southwest
Thu, Oct 1 - Sun, Oct 4
American Airlines Logo
6:48 pm - 2:00 pm
MKE
-
SXM
17h 12m
1 stop
American Airlines Logo
2:51 pm - 11:59 pm
SXM
-
MKE
11h 08m
1 stop
$620American Airlines
Wed, Nov 11 - Tue, Nov 17

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United Airlines flights from Milwaukee to Simpson Bay

Our best United Airlines deals on Milwaukee to Simpson Bay flight tickets
United Airlines
Jul 18
MKE7:23 pmMilwaukee-Mitchell
16h 10m
2 stops
SXM12:33 pmSimpson Bay Princess Juliana
Jul 25
SXM3:50 pmSimpson Bay Princess Juliana
19h 03m
2 stops
MKE9:53 amMilwaukee-Mitchell
$564
United Airlines
Oct 31
MKE5:00 amMilwaukee-Mitchell
8h 57m
1 stop
SXM2:57 pmSimpson Bay Princess Juliana
Nov 7
SXM5:00 pmSimpson Bay Princess Juliana
25h 35m
2 stops
MKE4:35 pmMilwaukee-Mitchell
$684
United Airlines
Oct 31
MKE5:00 amMilwaukee-Mitchell
8h 57m
1 stop
SXM2:57 pmSimpson Bay Princess Juliana
Nov 7
SXM5:00 pmSimpson Bay Princess Juliana
25h 35m
2 stops
MKE4:35 pmMilwaukee-Mitchell
$689

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Oct 24
MKE5:51 pmMilwaukee-Mitchell
20h 14m
2 stops
SXM3:05 pmSimpson Bay Princess Juliana
Nov 7
SXM5:24 pmSimpson Bay Princess Juliana
20h 16m
2 stops
MKE11:40 amMilwaukee-Mitchell
$538
American Airlines
Oct 24
MKE4:49 pmMilwaukee-Mitchell
21h 16m
2 stops
SXM3:05 pmSimpson Bay Princess Juliana
Nov 7
SXM2:15 pmSimpson Bay Princess Juliana
21h 23m
1 stop
MKE9:38 amMilwaukee-Mitchell
$548
American Airlines
Aug 10
MKE6:00 pmMilwaukee-Mitchell
20h 39m
2 stops
SXM3:39 pmSimpson Bay Princess Juliana
Aug 21
SXM2:42 pmSimpson Bay Princess Juliana
9h 17m
1 stop
MKE10:59 pmMilwaukee-Mitchell
$570

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 June 16, 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
Quickest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 10/1

5:30 am-1:50 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sun 10/4

3:20 pm-11:52 pm

1 stop9h 32m

$493

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 10/24

5:51 pm-3:05 pm

2 stops20h 14m

Simpson Bay Princess Juliana

Sat 11/7

5:24 pm-11:40 am

2 stops20h 16m

$538

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

$547

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 10/24

4:49 pm-3:05 pm

2 stops21h 16m

Simpson Bay Princess Juliana

Sat 11/7

2:15 pm-9:38 am

1 stop21h 23m

$548

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 7/18

7:23 pm-12:33 pm

2 stops16h 10m

Simpson Bay Princess Juliana

Sat 7/25

3:50 pm-9:53 am

2 stops19h 03m

$564

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 8/10

6:00 pm-3:39 pm

2 stops20h 39m

Simpson Bay Princess Juliana

Fri 8/21

2:42 pm-10:59 pm

1 stop9h 17m

$570

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

$598

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 11/11

6:48 pm-4:20 pm

2 stops19h 32m

Simpson Bay Princess Juliana

Tue 11/17

2:51 pm-9:38 am

2 stops20h 47m

$605

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 10/1

8:00 pm-2:00 pm

2 stops17h 00m

Simpson Bay Princess Juliana

Sun 10/4

3:00 pm-11:35 pm

1 stop9h 35m

$616

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 11/11

6:48 pm-2:00 pm

1 stop17h 12m

Simpson Bay Princess Juliana

Tue 11/17

2:51 pm-11:59 pm

1 stop11h 08m

$620

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, 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
8,405 reviews
Search Delta flights
United AirlinesPriceFrom $478Free CancellationRating
7.4
9,842 reviews
Search United Airlines flights
American AirlinesPriceFrom $605Free CancellationRating
7.1
11,665 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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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
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