$232 Find Cheap Flights from Milwaukee to St. Maarten

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 St. Maarten departing on 1/9. 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

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Cheap Flights from Milwaukee to St. Maarten

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Simpson Bay
Simpson Bay1 stop$497
Simpson Bay
Simpson Bay1 stop$497

Book Cheap Milwaukee to St. Maarten Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to St. Maarten 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 St. Maarten

Sun, Aug 31 - Sun, Sep 7
Delta Logo
6:00 am - 1:56 pmMKE-SXM
6h 56m1 stop
Delta Logo
3:21 pm - 11:36 pmSXM-MKE
9h 15m1 stop
$497Delta
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Wed, Oct 29 - Wed, Nov 5
American Airlines Logo
2:05 pm - 1:37 pmMKE-SXM
22h 32m2 stops
American Airlines Logo
3:20 pm - 8:00 amSXM-MKE
18h 40m2 stops
$617American Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
United Airlines Logo
2:45 pm - 3:57 pmMKE-SXM
24h 12m1 stop
United Airlines Logo
2:51 pm - 5:17 pmSXM-MKE
28h 26m1 stop
$619United Airlines
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Sun, Aug 31 - Sun, Sep 7
American Airlines Logo
5:28 pm - 1:45 pmMKE-SXM
19h 17m2 stops
American Airlines Logo
2:20 pm - 3:15 pmSXM-MKE
25h 55m2 stops
$622American Airlines
Find Deal
Sun, Aug 31 - Sun, Sep 7
American Airlines Logo
7:20 am - 1:20 pmMKE-SXM
29h 00m1 stop
American Airlines Logo
2:20 pm - 3:15 pmSXM-MKE
25h 55m2 stops
$631American Airlines
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Wed, Oct 29 - Wed, Nov 5
Delta Logo
5:17 am - 1:49 pmMKE-SXM
7h 32m1 stop
Delta Logo
4:14 pm - 11:55 pmSXM-MKE
9h 41m1 stop
$727Delta
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Fri, Dec 26 - Fri, Jan 2
American Airlines Logo
6:48 pm - 12:10 pmMKE-SXM
15h 22m1 stop
American Airlines Logo
2:15 pm - 2:52 pmSXM-MKE
26h 37m1 stop
$993American Airlines
Find Deal
Fri, Dec 26 - Fri, Jan 2
American Airlines Logo
5:18 pm - 12:10 pmMKE-SXM
16h 52m2 stops
American Airlines Logo
2:15 pm - 2:52 pmSXM-MKE
26h 37m1 stop
$1,130American Airlines
Find Deal
Fri, Dec 26 - Fri, Jan 2
American Airlines Logo
5:00 pm - 2:00 pmMKE-SXM
19h 00m2 stops
American Airlines Logo
3:30 pm - 9:44 amSXM-MKE
20h 14m2 stops
$1,395American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Milwaukee to St. Maarten flights

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

Which airlines provide the cheapest flights from Milwaukee to St. Maarten?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Milwaukee to St. Maarten were found on Delta ($497) and American Airlines ($617).


Good to know

Low seasonMay
Cheapest flight$232
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Milwaukee to Simpson Bay

FAQs - booking St. Maarten flights

  • How does KAYAK find such low prices on flights from Milwaukee to St. Maarten?

    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 St. Maarten.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to St. Maarten 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 St. Maarten?

    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 from Milwaukee to St. Maarten with an airline and back with another airline.

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

    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 from Milwaukee to St. Maarten up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to St. Maarten?

    The cheapest time of day to fly to St. Maarten is generally in the evening, when round-trip flights cost $614 on average. Morning departures are around 9% more expensive than evening flights, on average. The most expensive time of day to fly to St. Maarten is generally in the morning, which is peak travel time and where the average cost of a ticket is $669.

Reviews of the top airlines flying 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
DeltaOverall score based on 7983 reviews
7.3Food
8.2Boarding
7.9Comfort
8.5Crew
7.9Entertainment
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

Everything you need to know for your flight from Milwaukee to St. Maarten

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