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).

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.

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) - 45% of one-stop connections • Orlando (MCO) - 24% of one-stop connections • Chicago O'Hare Intl (ORD) - 16% of one-stop connections • Newark (EWR) - 6% of one-stop connections

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

Yes. Flexible dates can save you up to 20% on flights from Milwaukee to Simpson Bay. Sunday is the cheapest departure day at $643 round-trip on average, while Monday is the most expensive at $803, a difference of $160. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

How long is a flight from Milwaukee to Simpson Bay?

A nonstop flight from Milwaukee to Simpson Bay takes 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.

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 $577 to $3,388. That means the highest observed fare was about 6x higher than the lowest one.

How are flight prices from Milwaukee to Simpson Bay looking right now?

One-way fares from Milwaukee to Simpson Bay are currently higher than usual. Average one-way flight prices are about $525, which is 81% above the typical average for this route.

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

Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 8h 14m, compared with 8h 27m via Atlanta Hartsfield-Jackson (ATL) and 8h 34m via Orlando (MCO).

What is the time difference between Milwaukee and Simpson Bay?

Simpson Bay is 2 hours ahead of Milwaukee (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

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 averaging $40 for economy cars. Top options include: • Right Cars • Ace • Budget • Avis • Final Rentals

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

Round-trip flights from Milwaukee to Simpson Bay range from $603 to $791, with an average of $683 over the past 12 months. Anything below $603 counts as a good deal.

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

Round-trip flights from Milwaukee to Simpson Bay typically range from $603 to $791. The lowest price found in the past 5 days was $577, on American Airlines.

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

Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Milwaukee to Simpson Bay. It’s 6% cheaper than the average day, while Monday is the most expensive, with prices 17% higher.

Which airline is the cheapest to fly from Milwaukee to Simpson Bay?

American Airlines ($577) and Southwest ($592) are the cheapest airlines to fly round-trip from Milwaukee to Simpson Bay according to KAYAK data over the last 5 days.

What’s the most popular layover airport when flying from Milwaukee to Simpson Bay?

Atlanta Hartsfield-Jackson (ATL) is the most popular layover for the Milwaukee to Simpson Bay route. 45% of KAYAK users who booked 1-stop round-trips over the past 3 months connected via ATL.

What is the cheapest layover airport when flying from Milwaukee to Simpson Bay?

Flights via Chicago O'Hare Intl (ORD) offer the most affordable fares, with an average round-trip price of $578. Based on KAYAK data over the past 3 months.

When flying from Milwaukee to Simpson Bay which airport offers the shortest layover?

Charlotte Douglas (CLT) had the shortest average connection time for Milwaukee to Simpson Bay layovers at 4h 49m over the past 3 months.

$255 CHEAP FLIGHTS from Milwaukee to Simpson Bay (MKE - SXM)

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Never overpay with our price tracking tools.

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Cheapest round-trip

$577

Typical prices: $603-$791

American Airlines

Fri 1/12Tue 1/16

MKE - SXM • 1 stop

Cheapest one-way

$255

Typical prices: $228-$401

United Airlines

Mon 1/1

MKE - SXM • 2 stops

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

When to travel

November

Cheapest • 13% price drop

February

Most popular

Good to know

Top layover airports

Chicago O'Hare Intl (ORD)

Cheapest • Avg $578 (round-trip)

Charlotte Douglas (CLT)

Shortest trip • 8h 14m (one-way)

Insights

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We hope you love your trip to Simpson Bay!

Flight Deals

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

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

Round-trip

One-way

Recent round-trip flight deals from Milwaukee to Simpson Bay

Tue, Jan 12 - Sat, Jan 16

6:20 am - 4:26 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

8h 06m1 stop Miami

3:57 pm - 10:36 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 39m1 stop Chicago O'Hare Intl

$577American Airlines

Sat, Feb 6 - Thu, Feb 11

5:17 am - 3:07 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 50m1 stop Chicago O'Hare Intl

3:23 pm - 11:54 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 31m1 stop Miami

$577American Airlines

Sun, Jan 10 - Mon, Jan 18

5:15 am - 2:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 00m1 stop Orlando

4:40 pm - 11:30 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 50m1 stop Baltimore/Washington

$592Southwest

Sun, Jan 10 - Sun, Jan 17

3:51 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 59m2 stops Chicago O'Hare Intl Newark

2:52 pm - 8:07 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

19h 15m2 stops Newark Chicago O'Hare Intl

$596United Airlines

Sun, Jan 10 - Sun, Jan 17

6:29 pm - 1:50 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

17h 21m1 stop Newark

2:52 pm - 10:00 amSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

21h 08m2 stops Newark Chicago O'Hare Intl

$596United Airlines

Sun, Jan 10 - Mon, Jan 18

4:25 pm - 2:15 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

19h 50m2 stops Las Vegas Harry Reid Intl Orlando

4:40 pm - 11:30 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

8h 50m1 stop Baltimore/Washington

$596Southwest

Tue, May 4 - Tue, May 11

5:55 am - 2:05 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 10m1 stop Atlanta Hartsfield-Jackson

1:55 pm - 11:49 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

10h 54m1 stop Atlanta Hartsfield-Jackson

$607Delta

Tue, Dec 15 - Tue, Dec 22

5:20 am - 2:40 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

7h 20m1 stop Atlanta Hartsfield-Jackson

1:40 pm - 8:48 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

9h 08m1 stop Atlanta Hartsfield-Jackson

$632Delta

Tue, Dec 15 - Tue, Dec 22

8:30 am - 3:25 pmMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

28h 55m3 stops Chicago O'Hare Intl Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

4:50 pm - 6:19 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

27h 29m3 stops Toronto Pearson Intl Miami Minneapolis St Paul

$1,121Multiple Airlines

Tue, Dec 15 - Tue, Dec 22

12:15 pm - 11:55 amMKE Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana

21h 40m2 stops Chicago O'Hare Intl Montreal Pierre Elliott Trudeau Intl

4:50 pm - 6:19 pmSXM Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell

27h 29m3 stops Toronto Pearson Intl Miami Minneapolis St Paul

$1,234Multiple Airlines

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 with more confidence.

Prices

Airlines

Layovers

How much is a round-trip flight from Milwaukee to Simpson Bay? This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Milwaukee to Simpson Bay departing in january.
What's the cheapest day of the week to fly from Milwaukee to Simpson Bay?: Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Milwaukee to Simpson Bay. It’s 6% cheaper than the average day, while Monday is the most expensive, with prices 17% higher.

Find deals

Low season	May
High season	February
Cheapest flight	$255

Beat the crowds with an average 89% drop in travelers.

The most popular month to fly with an average 125% increase in travelers.

One-way 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

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

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 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 $603 to $791, with an average of $683 over the past 12 months. Anything below $603 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 $577 to $3,388. That means the highest observed fare was about 6x higher than the lowest one.
How are flight prices from Milwaukee to Simpson Bay looking right now?
One-way fares from Milwaukee to Simpson Bay are currently higher than usual. Average one-way flight prices are about $525, which is 81% above the typical average for this route.
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 averaging $40 for economy cars. Top options include:

• Right Cars
• Ace
• Budget
• Avis
• Final Rentals
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) - 45% of one-stop connections
• Orlando (MCO) - 24% of one-stop connections
• Chicago O'Hare Intl (ORD) - 16% of one-stop connections
• Newark (EWR) - 6% of one-stop connections
Can I save money by using flexible dates for flights from Milwaukee to Simpson Bay?
Yes. Flexible dates can save you up to 20% on flights from Milwaukee to Simpson Bay. Sunday is the cheapest departure day at $643 round-trip on average, while Monday is the most expensive at $803, a difference of $160.

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 Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 8h 14m, compared with 8h 27m via Atlanta Hartsfield-Jackson (ATL) and 8h 34m via Orlando (MCO).
What is the time difference between Milwaukee and Simpson Bay?
Simpson Bay is 2 hours ahead of Milwaukee (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

If your dates are flexible, aim for a Sunday departure and avoid flying on Monday. On this route, Sunday flights average $643, about $160 less than Monday fares (20% savings) based on the last 12 months.
If you can choose when to travel, plan your Milwaukee to Simpson Bay trip for November. Fares historically average $595 round-trip in that month - typically $672 less than the most expensive month, which is December (based on the last 12 months).
If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.

• Simpson Bay Resort Marina & Spa
• Hilton Vacation Club Flamingo Beach St. Maarten
• The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

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MKE - SXM

$255 Find Cheap Flights from Milwaukee to Simpson Bay - Compare and Save

Everything you should know

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

Recent round-trip flight deals from Milwaukee to Simpson Bay

Recent one-way flight deals from Milwaukee to Simpson Bay

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

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

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

Which airline is the cheapest to fly from Milwaukee to Simpson Bay?

What’s the most popular layover airport when flying from Milwaukee to Simpson Bay?

What is the cheapest layover airport when flying from Milwaukee to Simpson Bay?

When flying from Milwaukee to Simpson Bay which airport offers the shortest layover?

Key details for Milwaukee to Simpson Bay flights

Low season

High season

Cheapest flight

When to book flights from Milwaukee to Simpson Bay

Your Milwaukee to Simpson Bay flight questions, answered

Your guide to booking Milwaukee to Simpson Bay flights

More options for your flight from Milwaukee to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights from Milwaukee to Simpson Bay

Find direct flights to and from Milwaukee and Simpson Bay

Flights to other popular destinations