MKE - SXM

$496 Find Cheap Flights from Milwaukee to Simpson Bay - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$519
Typical prices: $656-$866
Southwest
Tue 10/30Tue 11/6
MKE - SXM • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Milwaukee and Simpson Bay. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
November
Cheapest • 20% price drop
January
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Chicago O'Hare Intl (ORD)
Cheapest • Avg $613 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 8h 18m (one-way)
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Flight Deals

Cheap Flights from Milwaukee to Simpson Bay (MKE-SXM)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Simpson Bay

Fri, Oct 30 - Fri, Nov 6
Southwest Logo
5:00 am - 2:05 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
8h 05m1 stop Orlando
Southwest Logo
4:40 pm - 11:35 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
8h 55m1 stop Baltimore/Washington
$519Southwest
Fri, Oct 30 - Fri, Nov 6
Southwest Logo
5:00 am - 2:05 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
8h 05m1 stop Orlando
Southwest Logo
3:15 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
10h 40m2 stops Orlando Nashville Intl
$524Southwest
Sat, Jan 23 - Fri, Jan 29
Delta Logo
6:40 pm - 2:40 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
18h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 11:49 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
12h 09m1 stop Atlanta Hartsfield-Jackson
$526Delta
Tue, Jan 19 - Sat, Jan 23
Delta Logo
5:55 am - 2:40 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
6h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:25 pm - 11:49 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
8h 24m1 stop Atlanta Hartsfield-Jackson
$526Delta
Sat, Jan 30 - Sat, Feb 6
United Airlines Logo
3:42 pm - 1:50 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
20h 08m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
United Airlines Logo
2:10 pm - 11:11 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
11h 01m1 stop Chicago O'Hare Intl
$526United Airlines
Sat, Jan 30 - Sat, Feb 6
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 - 7:11 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
19h 01m1 stop Chicago O'Hare Intl
$526United Airlines
Fri, Oct 30 - Fri, Nov 6
Southwest Logo
5:00 am - 2:05 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
8h 05m1 stop Orlando
Southwest Logo
3:15 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
10h 40m2 stops Orlando Nashville Intl
$542Southwest
Sat, Jan 30 - Mon, Feb 8
American Airlines Logo
12:10 pm - 12:26 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
22h 16m2 stops Charlotte Douglas Miami
American Airlines Logo
1:01 pm - 11:14 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
12h 13m1 stop Miami
$559American Airlines
Tue, Jan 12 - Sat, Jan 16
American Airlines Logo
12:10 pm - 12:26 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
22h 16m2 stops Charlotte Douglas Miami
American Airlines Logo
4:02 pm - 9:11 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
19h 09m2 stops Charlotte Douglas Chicago O'Hare Intl
$559American Airlines
Fri, Jan 22 - Fri, Jan 29
WestJet Logo
5:00 pm - 12:30 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
17h 30m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
WestJet Logo
4:20 pm - 8:45 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
18h 25m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
$2,808WestJet
Booking Insights

Price, demand and travel trends for Milwaukee to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Milwaukee to Simpson Bay with more confidence.

How much is a round-trip flight from Milwaukee to Simpson Bay?

Round-trip flights from Milwaukee to Simpson Bay start at $519. Prices are below average for this route right now, with typical round-trip fares ranging from $656 to $866. The lowest price found in the past 5 days was $519 on Southwest.

What's the cheapest day of the week to fly from Milwaukee to Simpson Bay?

Sunday is the cheapest day of the week to fly from Milwaukee to Simpson Bay, it is 12% cheaper than the average day. Monday is the most expensive day with flight prices 15% higher than average. Based on deals found by KAYAK users in the last 12 months.

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Key details for Milwaukee to Simpson Bay flights

Low season

May

Cheapest flight

$519
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Milwaukee to Simpson Bay

When to book flights from Milwaukee to Simpson Bay

Are your dates flexible? Find out the best times to travel from Milwaukee to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Milwaukee to Simpson Bay flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • What cabin classes can I book on flights from Milwaukee to Simpson Bay?

    Only Economy Class is available on flights from Milwaukee to Simpson Bay.

  • How long is a flight from Milwaukee to Simpson Bay?

    A nonstop flight from Milwaukee to Simpson Bay takes 0h 00m, covering 2,248 miles.

  • Do I need a passport to fly from Milwaukee to Simpson Bay?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Milwaukee to Simpson Bay flight?

    Round-trip flights from Milwaukee to Simpson Bay range from $656 to $866, with an average of $740 over the past 12 months. Anything below $656 counts as a good deal.

  • Have flight prices from Milwaukee to Simpson Bay changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $519 to $2,679. That means the highest observed fare was about 5x higher than the lowest one.

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
    • Ace
    • Right Cars
    • Europcar
    • Budget
    • Alamo

  • Which airports can I use when flying from Milwaukee to Simpson Bay?

    Flights from Milwaukee to Simpson Bay usually depart from Milwaukee-Mitchell (MKE) and arrive at Simpson Bay Princess Juliana (SXM).

  • Which airports do connecting flights from Milwaukee to Simpson Bay pass through?

    One-stop flights from Milwaukee to Simpson Bay most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 53% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 19% of one-stop connections
    • Orlando (MCO) - 13% of one-stop connections
    • Miami (MIA) - 6% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Milwaukee to Simpson Bay?

    On the Milwaukee to Simpson Bay route, being flexible with your departure day can save you up to 23%. Sunday is the cheapest day at $656 round-trip on average, while Monday is the most expensive at $851: a $195 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How much time can I save by choosing a different layover airport from Milwaukee to Simpson Bay?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 8h 18m, compared with 8h 34m via Orlando (MCO) and 8h 49m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Milwaukee and Simpson Bay?

    Simpson Bay is 1 hour ahead of Milwaukee (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Milwaukee to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.

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