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MKE - SXM

Find cheap flights from Milwaukee to Simpson Bay from $785

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Simpson Bay departing on 5/30. 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
0 bags
Sat 6/1
Sat 6/8

Search hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Simpson Bay, as well as popular online travel agencies
In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
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6:00 am - 1:40 pmMKE-SXM
6h 40m1 stop
3:10 pm - 9:31 amSXM-MKE
19h 21m1 stop
$785Delta
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Thu, May 30 - Mon, Jun 3

Flights from Milwaukee to Simpson Bay - Travel Insights & Trends

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 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 September, where tickets cost $642 on average. On the other hand, the most expensive months are July and August, where the average cost of tickets is $1,155 and $997 respectively.

How far in advance should I book a flight from Milwaukee to Simpson Bay?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Milwaukee to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Milwaukee to Simpson Bay, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 71 days before departure.

Good to know

Low season

August

High season

January

Cheapest flight

$785
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 2% 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 3 days, the lowest price for a flight from Milwaukee to Simpson Bay was $785 for a round-trip ticket.

  • 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?

    SkyTeam is the only airline alliance operating flights between Milwaukee and Simpson Bay.

  • 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.

See more FAQs

Top 3 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
DeltaOverall score based on 10861 reviews
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
8.6Crew
Airline reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

8.0 ExcellentAnonymous, May 2024ATL - ATW
Read more about Delta reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

All flights were on time and boarding was issue free

Terrible! The plane was old and you are required to connect your own device to their Wi-Fi rather than have entertainment options in the back of the seat in front of you. The Wi-Fi went out during the flight and there was only one plug for the devices every two seats. Three out of five surrounding my family did not work. The seats and spaces under them were so small I could not fit my backpack, which I’ve always brought on flights and fit before no problem. The crew were unpleasant and patronizing.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Food was terrible Not many options Stewards dont care Delay

Water service would be great. The way they board is terrible. Slow passengers first😂😂 They need to smart up a bit

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Not being able to purchase my check in baggage online was a negative.

LATE LATE LATE!!! Plagued by late AA flights on this trip. Such a drag. This one was by far the worst.

WiFi connected but only let you go to the AA website, not even text messaging worked.

Too bad that first class seats do not recline significantly causing discomfort

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Not sure why JAL partnered with American Airlines because their service is no where near similar. Flight attendants were not friendly and didn’t smile. Food was horrible…

this is starting to seem like an american airlines standard. delayed flights and fake apologies… getting tired of it

Milwaukee - Simpson Bay Flights

Departure:

Milwaukee (MKE)United States

Destination:

Simpson Bay (SXM)St. Maarten

Cabin classes: