MKE - SXM

$352 Find Cheap Flights from Milwaukee to Simpson Bay - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Simpson Bay departing on 8/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$510
Typical prices: $545-$738
American Airlines
Sat 10/31Sat 11/7
MKE - SXM • 2 stops
Cheapest one-way
$352
Delta
Fri 8/14
MKE - SXM • 1 stop
Top airlines
Cheapest • from $496 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Milwaukee and Simpson Bay. You'll need at least 1 connection.
Insights
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Top layover airports
Cheapest • Avg $631 (round-trip)
Shortest trip • 7h 17m (one-way)
Insights
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Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Simpson Bay

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
3:26 pm - 10:02 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
20h 36m2 stops Miami Charlotte Douglas
$510American Airlines
Sat, Sep 19 - Sat, Sep 26
American Airlines Logo
12:22 pm - 1:23 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
24h 01m2 stops Dallas/Fort Worth Miami
American Airlines Logo
2:23 pm - 8:01 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
18h 38m2 stops Miami Chicago O'Hare Intl
$510American Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
6:27 pm - 3:39 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
20h 12m2 stops Charlotte Douglas Miami
American Airlines Logo
4:39 pm - 8:48 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
17h 09m2 stops Miami Chicago O'Hare Intl
$510American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
4:12 pm - 1:22 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
20h 10m2 stops Charlotte Douglas Miami
American Airlines Logo
2:23 pm - 8:01 amSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
18h 38m2 stops Miami Chicago O'Hare Intl
$510American Airlines
Sat, Oct 24 - Sat, Oct 31
United Airlines Logo
2:20 pm - 12:50 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
21h 30m2 stops Chicago O'Hare Intl Newark
United Airlines Logo
1:10 pm - 10:15 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
10h 05m1 stop Chicago O'Hare Intl
$579United Airlines
Sat, Oct 31 - Sat, Nov 7
Delta Logo
5:30 am - 1:40 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
7h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:05 pm - 11:53 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
9h 48m1 stop Atlanta Hartsfield-Jackson
$598Delta
Sat, Sep 19 - Sat, Sep 26
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
$598Delta
Sat, Sep 19 - Sat, Sep 26
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
$628Delta
Sat, Oct 24 - Sat, Oct 31
United Airlines Logo
6:38 pm - 12:50 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
17h 12m1 stop Newark
United Airlines Logo
1:10 pm - 8:50 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
8h 40m1 stop Chicago O'Hare Intl
$667United Airlines
Wed, Nov 11 - Tue, Nov 17
United Airlines Logo
7:03 pm - 1:50 pmMKE  Milwaukee-Mitchell-SXM Simpson Bay Princess Juliana
16h 47m1 stop Newark
United Airlines Logo
2:52 pm - 10:47 pmSXM  Simpson Bay Princess Juliana-MKE Milwaukee-Mitchell
9h 55m1 stop Newark
$1,050United Airlines
Booking Insights

KAYAK's insights & trends for Milwaukee to Simpson Bay flights

Get data-powered insights and trends into flights from Milwaukee to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Milwaukee to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to Simpson Bay is April, where tickets cost $0 (return) on average. On the other hand, the most expensive months are June and February, where the average cost of round-trip tickets is $874 and $857 respectively.

Good to know

Low season

August

Cheapest flight

$352
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 9% 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
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.

FAQs for booking flights from Milwaukee to Simpson Bay

  • What is the cheapest flight from Milwaukee to Simpson Bay?

    In the last 5 days, the lowest price for a flight from Milwaukee to Simpson Bay was $352 for a one-way ticket and $496 for a round-trip.

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

    A passport is required to fly from Milwaukee to Simpson Bay.

  • Which airports will I be using when flying from Milwaukee to Simpson Bay?

    On your way to Simpson Bay, you’ll fly out from Milwaukee-Mitchell. You’ll be landing at Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Milwaukee to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Milwaukee to Simpson Bay?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Milwaukee and Simpson Bay, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Milwaukee to Simpson Bay, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Milwaukee to Simpson Bay are Southwest and Delta. With an average price for the route of $785 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $743 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Milwaukee to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Milwaukee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Milwaukee with another airline. Booking your flights between Milwaukee and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Milwaukee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Milwaukee to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milwaukee to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4220 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

10.0 ExcellentAnonymous, Aug 2026
Read more Southwest reviews

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

the flight got cancelled - few hours before the departure time - no time to change

This a short easy flight. No food or drink but that was not an issue since we were only in the air for 35 minutes.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

Flight delayed for people who “should’nt have gotten thru tsa” had to look for their bags took two hours With no explanation had never happened Poorly handled

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

Staff and flight attendants were very polite. Flight was smooth. My seat on the plane was a bit broken so it would not stay in upright position but it was fine for the most part.

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was over an hour delayed. The problem was they had the wrong aircraft at the gate, Joe in the world does that happen?

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Baggage claim took too long and priority bags were not delivered first.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight from Milwaukee to Simpson Bay

Information on your arrival and departure airports