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Cheap flights from Milwaukee to Simpson Bay from $499

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 10/31. 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.
American Airlines Logo
7:19 pm - 4:31 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
20h 12m2 stops Chicago O'Hare Intl Miami
American Airlines Logo
3:26 pm - 7:48 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
18h 22m2 stops Miami Chicago O'Hare Intl
$499American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
7:19 pm - 4:31 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
20h 12m2 stops Chicago O'Hare Intl Miami
American Airlines Logo
5:33 pm - 10:02 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
18h 29m2 stops Miami Charlotte Douglas
$499American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
7:19 pm - 2:26 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
18h 07m2 stops Chicago O'Hare Intl Miami
American Airlines Logo
4:20 pm - 11:06 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
8h 46m1 stop Charlotte Douglas
$499American Airlines
Sat, Oct 31 - Sat, Nov 7
Delta Logo
5:30 am - 1:53 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
7h 23m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:18 pm - 11:48 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
9h 30m1 stop Atlanta Hartsfield-Jackson
$501Delta
Sun, Sep 27 - Sun, Oct 4
United Airlines Logo
6:00 am - 3:57 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
7h 57m1 stop Chicago O'Hare Intl
United Airlines Logo
2:10 pm - 8:56 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
8h 46m1 stop Chicago O'Hare Intl
$519United Airlines
Sat, Dec 12 - Thu, Dec 17
Southwest Logo
5:25 am - 2:20 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
6h 55m1 stop Orlando
Southwest Logo
2:30 pm - 12:10 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
11h 40m1 stop Orlando
$555Southwest
Sat, Nov 14 - Sat, Nov 21
Southwest Logo
5:00 am - 2:05 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
8h 05m1 stop Orlando
Southwest Logo
3:05 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
9h 50m1 stop Orlando
$560Southwest
Sun, Oct 18 - Sun, Oct 25
Delta Logo
12:20 pm - 12:15 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
21h 55m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
Delta Logo
5:25 pm - 9:22 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
17h 57m1 stop Atlanta Hartsfield-Jackson
$582Delta
Tue, Jan 12 - Sat, Jan 16
United Airlines Logo
6:45 pm - 1:50 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
17h 05m1 stop Newark
United Airlines Logo
2:52 pm - 11:27 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
10h 35m1 stop Newark
$590United Airlines
Mon, Jan 11 - Thu, Jan 14
Delta Logo
12:20 pm - 12:15 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
21h 55m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
Delta Logo
5:25 pm - 11:49 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
8h 24m1 stop Atlanta Hartsfield-Jackson
$607Delta
Tue, Jan 12 - Sat, Jan 16

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Southwest flights from Milwaukee to Simpson Bay

Our best Southwest deals on Milwaukee to Simpson Bay flight tickets
Southwest
Oct 18
MKE5:00 amMilwaukee-Mitchell
8h 05m
1 stop
SXM2:05 pmSimpson Bay Princess Juliana
Oct 25
SXM3:05 pmSimpson Bay Princess Juliana
9h 50m
1 stop
MKE11:55 pmMilwaukee-Mitchell
$560
Southwest
Oct 18
MKE8:10 pmMilwaukee-Mitchell
16h 55m
2 stops
SXM2:05 pmSimpson Bay Princess Juliana
Oct 25
SXM3:05 pmSimpson Bay Princess Juliana
9h 50m
1 stop
MKE11:55 pmMilwaukee-Mitchell
$565
Southwest
Sep 27
MKE7:20 pmMilwaukee-Mitchell
17h 45m
2 stops
SXM2:05 pmSimpson Bay Princess Juliana
Oct 4
SXM3:05 pmSimpson Bay Princess Juliana
9h 50m
1 stop
MKE11:55 pmMilwaukee-Mitchell
$580

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets
Delta
Jan 12
MKE12:20 pmMilwaukee-Mitchell
21h 55m
2 stops
SXM12:15 pmSimpson Bay Princess Juliana
Jan 16
SXM5:25 pmSimpson Bay Princess Juliana
17h 57m
1 stop
MKE9:22 amMilwaukee-Mitchell
$582
Delta
Oct 1
MKE5:30 amMilwaukee-Mitchell
7h 23m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Oct 5
SXM3:18 pmSimpson Bay Princess Juliana
9h 30m
1 stop
MKE11:48 pmMilwaukee-Mitchell
$639
Delta
Sep 30
MKE5:30 amMilwaukee-Mitchell
7h 23m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Oct 5
SXM3:18 pmSimpson Bay Princess Juliana
9h 30m
1 stop
MKE11:48 pmMilwaukee-Mitchell
$658

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 August 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

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/31

7:19 pm-4:31 pm

2 stops20h 12m

Simpson Bay Princess Juliana

Sat 11/7

3:26 pm-7:48 am

2 stops18h 22m

$499

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/31

7:19 pm-4:31 pm

2 stops20h 12m

Simpson Bay Princess Juliana

Sat 11/7

5:33 pm-10:02 am

2 stops18h 29m

$499

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 10/31

7:19 pm-2:26 pm

2 stops18h 07m

Simpson Bay Princess Juliana

Sat 11/7

4:20 pm-11:06 pm

1 stop8h 46m

$499

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 9/27

5:30 am-1:53 pm

1 stop7h 23m

Simpson Bay Princess Juliana

Sun 10/4

3:18 pm-11:48 pm

1 stop9h 30m

$501
Quickest round-trip

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 12/12

6:00 am-3:57 pm

1 stop7h 57m

Simpson Bay Princess Juliana

Thu 12/17

2:10 pm-8:56 pm

1 stop8h 46m

$519

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sat 11/14

5:25 am-2:20 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 11/21

2:30 pm-12:10 am

1 stop11h 40m

$555

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Sun 10/18

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sun 10/25

3:05 pm-11:55 pm

1 stop9h 50m

$560

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/12

12:20 pm-12:15 pm

2 stops21h 55m

Simpson Bay Princess Juliana

Sat 1/16

5:25 pm-9:22 am

1 stop17h 57m

$582

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Mon 1/11

6:45 pm-1:50 pm

1 stop17h 05m

Simpson Bay Princess Juliana

Thu 1/14

2:52 pm-11:27 pm

1 stop10h 35m

$590

MilwaukeeSimpson Bay

MKE Milwaukee-Mitchell - SXM Simpson Bay Princess Juliana

MKESXM

Milwaukee-Mitchell

Tue 1/12

12:20 pm-12:15 pm

2 stops21h 55m

Simpson Bay Princess Juliana

Sat 1/16

5:25 pm-11:49 pm

1 stop8h 24m

$607

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, July 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 July, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $0.

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 10m

Direct flights

None
The fastest flight from Milwaukee to Simpson Bay takes 7h 10m
There are no direct flights from Milwaukee to Simpson Bay. There are no popular flight routes from Milwaukee to Simpson Bay.
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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 10m.

  • 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
United AirlinesPriceFrom $478Free CancellationRating
7.4
10,104 reviews
Search United Airlines flights
DeltaPriceFrom $483Free CancellationRating
7.8
8,502 reviews
Search Delta flights
American AirlinesPriceFrom $605Free CancellationRating
7.1
11,950 reviews
Search American Airlines flights
SouthwestPriceFrom $665Free CancellationRating
8.0
4,217 reviews
Search Southwest 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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