$255 Find Cheap Flights from Milwaukee to St. Maarten - Compare and Save

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Price, demand and travel trends for Milwaukee to St. Maarten flights

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

What are the cheapest fares from Milwaukee to St. Maarten right now?

The cheapest fare from Milwaukee to St. Maarten in the last week was $577 round-trip, to Simpson Bay Princess Juliana (SXM).

Which airport in St. Maarten is the cheapest to fly to from Milwaukee?

All flights from Milwaukee to St. Maarten arrive at Simpson Bay Princess Juliana (SXM). On average, round-trip fares are around $683.

What’s the cheapest day to fly from Milwaukee to St. Maarten?

Sunday tends to be the cheapest day to fly from Milwaukee to St. Maarten, while Monday is the most expensive. Fares run about 20% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Milwaukee to St. Maarten?

Data from the past 12 months shows it's cheapest to fly to St. Maarten during the morning with average prices of $681. The evening is the most expensive time to fly, with average prices of $809.

Key details for Milwaukee to St. Maarten flights

Low season

May

Cheapest flight

$152
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

Your Milwaukee to St. Maarten flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Milwaukee to St. Maarten?

    Yes. Fares from Milwaukee to St. Maarten are low right now. As a rule of thumb, a round-trip under $603 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Milwaukee to St. Maarten?

    Over the past 12 months, round-trip fares from Milwaukee to St. Maarten have ranged from $603 to $791.

  • What are the main airports serving St. Maarten?

    Flights to St. Maarten all arrive at Simpson Bay Princess Juliana (SXM).

  • What airlines fly nonstop from Milwaukee to St. Maarten?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Milwaukee to St. Maarten. One-stop options include:

    • Delta
    • Southwest
    • American Airlines

  • Which cabin classes are available on flights from Milwaukee to St. Maarten?

    On flights from Milwaukee to St. Maarten you can only book Economy Class.

Your guide to booking Milwaukee to St. Maarten flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for November when flights are typically cheapest and avoid December when prices are at their highest.
  • Flying on Sunday is usually the cheapest. Flights on Monday cost about 20% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in Simpson Bay, which is the most popular destination in St. Maarten. From there, it's easy to continue on to other popular destinations such as Lowlands, Philipsburg and Cole Bay.

Reviews of the top 4 airlines serving from Milwaukee to St. Maarten

 
Need help choosing which airline to fly with from Milwaukee to St. Maarten? 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 4212 reviews
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

Every single flight I take with southwest is delayed by at least one hour. Unbelievable

2.0 MediocreMatthew, Nov 2026
Read more Southwest reviews

Every single flight I take with southwest is delayed by at least one hour. Unbelievable

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

Boarding, crew and inflight entertainment was great. Could have better food options for a long flight. Paid money and got a seat with extra leg space but was asked to keep my carry on under the seat in front of me which defeats the purpose of buying a extra space seat.

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

Flight time kept changing and so did the gate. It was very frustrating

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 flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

The Delta assistsed services were awesome for my aunt. So very helpful.

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

Loved the easy process to board and the experience overall was smooth

Set on the plane for two hours before pushing off the gate due to the power source issue being fixed which was known before letting people board the plane. On top of that it was very hot as AC was not working properly. Terrible experience and limited communication provided by the crew on the status of the issue. They should let people deplane while issue is addressed instead of frying them and glued to the seats.

I am United’s newest fan. The planes are clean, the staff is so friendly and snacks are more than just old pretzel crumbles. The captain came and said hello! Truly amazing experience

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

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.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

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.

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.

More options for your flight from Milwaukee to St. Maarten

Complete your trip to St. Maarten with a hotel stay or car rental