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Cheap flights from Milwaukee to Simpson Bay from $187

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 3/8. 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
4:05 pm - 2:31 pm
MKE
-
SXM
20h 26m2 stops
American Airlines Logo
5:33 pm - 12:21 pm
SXM
-
MKE
20h 48m2 stops
$514American Airlines
Mon, Jan 19 - Thu, Jan 22
American Airlines Logo
4:05 pm - 1:45 pm
MKE
-
SXM
19h 40m1 stop
American Airlines Logo
3:31 pm - 10:58 pm
SXM
-
MKE
9h 27m1 stop
$518American Airlines
Mon, Jan 19 - Thu, Jan 22
American Airlines Logo
6:37 pm - 2:16 pm
MKE
-
SXM
17h 39m1 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
1:29 pm - 11:14 pm
SXM
-
MKE
11h 45m1 stop
$582American Airlines
Mon, Feb 16 - Mon, Feb 23
American Airlines Logo
6:37 pm - 12:29 pm
MKE
-
SXM
15h 52m2 stops
American Airlines Logo
3:17 pm - 11:14 pm
SXM
-
MKE
9h 57m1 stop
$587American Airlines
Thu, Feb 19 - Thu, Feb 26
Delta Logo
5:45 am - 1:54 pm
MKE
-
SXM
7h 09m1 stop
Delta Logo
12:55 pm - 11:57 pm
SXM
-
MKE
12h 02m1 stop
$595Delta
Tue, Mar 10 - Thu, Mar 19
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
American Airlines Logo
6:01 am - 4:28 pm
MKE
-
SXM
8h 27m1 stop
American Airlines Logo
12:29 pm - 11:59 pm
SXM
-
MKE
12h 30m1 stop
$620American Airlines
Fri, Mar 6 - Fri, Mar 13
American Airlines Logo
4:47 pm - 1:16 pm
MKE
-
SXM
18h 29m2 stops
American Airlines Logo
12:29 pm - 11:59 pm
SXM
-
MKE
12h 30m1 stop
$625American Airlines
Sat, Mar 7 - Sat, Mar 14
American Airlines Logo
10:26 am - 3:00 pm
MKE
-
SXM
26h 34m1 stop
American Airlines Logo
12:29 pm - 11:59 pm
SXM
-
MKE
12h 30m1 stop
$630American Airlines
Sat, Mar 7 - Sat, Mar 14

American Airlines flights from Milwaukee to Simpson Bay

Our best American Airlines deals on Milwaukee to Simpson Bay flight tickets
American Airlines
Jan 19
MKE4:05 pmMilwaukee-Mitchell
20h 26m
2 stops
SXM2:31 pmSimpson Bay Princess Juliana
Jan 22
SXM5:33 pmSimpson Bay Princess Juliana
20h 48m
2 stops
MKE12:21 pmMilwaukee-Mitchell
$514
Find similar
American Airlines
Jan 19
MKE4:05 pmMilwaukee-Mitchell
19h 40m
1 stop
SXM1:45 pmSimpson Bay Princess Juliana
Jan 22
SXM3:31 pmSimpson Bay Princess Juliana
9h 27m
1 stop
MKE10:58 pmMilwaukee-Mitchell
$518
Find similar
American Airlines
Feb 16
MKE6:01 amMilwaukee-Mitchell
8h 27m
1 stop
SXM4:28 pmSimpson Bay Princess Juliana
Feb 23
SXM3:17 pmSimpson Bay Princess Juliana
9h 57m
1 stop
MKE11:14 pmMilwaukee-Mitchell
$577
Find similar

Delta flights from Milwaukee to Simpson Bay

Our best Delta deals on Milwaukee to Simpson Bay flight tickets
Delta
Mar 10
MKE5:45 amMilwaukee-Mitchell
7h 09m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
Mar 19
SXM12:55 pmSimpson Bay Princess Juliana
12h 02m
1 stop
MKE11:57 pmMilwaukee-Mitchell
$595
Find similar
Delta
Jan 14
MKE5:30 amMilwaukee-Mitchell
7h 25m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
Jan 18
SXM1:55 pmSimpson Bay Princess Juliana
11h 35m
1 stop
MKE11:30 pmMilwaukee-Mitchell
$619
Find similar
Delta
Mar 12
MKE5:45 amMilwaukee-Mitchell
7h 09m
1 stop
SXM1:54 pmSimpson Bay Princess Juliana
Mar 20
SXM3:20 pmSimpson Bay Princess Juliana
30h 25m
2 stops
MKE8:45 pmMilwaukee-Mitchell
$664
Find similar

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 6, 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

Mon 1/19

4:05 pm-2:31 pm

2 stops20h 26m

Simpson Bay Princess Juliana

Thu 1/22

5:33 pm-12:21 pm

2 stops20h 48m

$514

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 1/19

4:05 pm-1:45 pm

1 stop19h 40m

Simpson Bay Princess Juliana

Thu 1/22

3:31 pm-10:58 pm

1 stop9h 27m

$518

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 2/16

6:37 pm-2:16 pm

1 stop17h 39m

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

1:29 pm-11:14 pm

1 stop11h 45m

$582

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Thu 2/19

6:37 pm-12:29 pm

2 stops15h 52m

Simpson Bay Princess Juliana

Thu 2/26

3:17 pm-11:14 pm

1 stop9h 57m

$587

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 3/10

5:45 am-1:54 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Thu 3/19

12:55 pm-11:57 pm

1 stop12h 02m

$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

Fri 3/6

6:01 am-4:28 pm

1 stop8h 27m

Simpson Bay Princess Juliana

Fri 3/13

12:29 pm-11:59 pm

1 stop12h 30m

$620

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 3/7

4:47 pm-1:16 pm

2 stops18h 29m

Simpson Bay Princess Juliana

Sat 3/14

12:29 pm-11:59 pm

1 stop12h 30m

$625

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

$630

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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 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

6h 57m

Direct flights

None
The fastest flight from Milwaukee to Simpson Bay takes 6h 57m
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 6h 57m.

  • 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
8,018 reviews
Search Delta flights
American AirlinesPriceFrom $587Free CancellationRating
7.2
11,084 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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