$303 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 1/14. 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

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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$635
Simpson Bay
Simpson Bay1 stop$635

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

Thu, Feb 19 - Tue, Feb 24
American Airlines Logo
6:50 pm - 1:50 pmMKE-SXM
17h 00m1 stop
American Airlines Logo
5:20 pm - 12:11 pmSXM-MKE
20h 51m2 stops
$635American Airlines
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Thu, Oct 30 - Thu, Nov 6
American Airlines Logo
8:16 pm - 3:15 pmMKE-SXM
17h 59m2 stops
American Airlines Logo
5:24 pm - 8:22 amSXM-MKE
16h 58m2 stops
$636American Airlines
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Sat, Jan 17 - Sat, Jan 24
United Airlines Logo
2:32 pm - 1:50 pmMKE-SXM
21h 18m2 stops
United Airlines Logo
2:40 pm - 10:56 pmSXM-MKE
10h 16m1 stop
$637United Airlines
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Fri, Oct 31 - Tue, Nov 4
American Airlines Logo
12:20 pm - 1:37 pmMKE-SXM
24h 17m2 stops
American Airlines Logo
5:24 pm - 11:38 amSXM-MKE
20h 14m2 stops
$657American Airlines
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Thu, Feb 19 - Tue, Feb 24
American Airlines Logo
6:50 pm - 1:50 pmMKE-SXM
17h 00m1 stop
American Airlines Logo
3:25 pm - 9:15 pmSXM-MKE
7h 50m1 stop
$660American Airlines
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Fri, Oct 31 - Tue, Nov 4
United Airlines Logo
6:39 pm - 2:57 pmMKE-SXM
19h 18m1 stop
United Airlines Logo
2:52 pm - 10:18 amSXM-MKE
21h 26m2 stops
$751United Airlines
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Mon, Dec 22 - Tue, Dec 30
United Airlines Logo
8:30 am - 1:50 pmMKE-SXM
27h 20m2 stops
United Airlines Logo
4:55 pm - 6:53 pmSXM-MKE
27h 58m2 stops
$837United Airlines
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Mon, Dec 22 - Mon, Dec 29
Delta Logo
5:40 am - 2:50 pmMKE-SXM
7h 10m1 stop
Delta Logo
1:50 pm - 7:58 pmSXM-MKE
8h 08m1 stop
$923Delta
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Mon, Dec 22 - Wed, Dec 31
Delta Logo
5:40 am - 2:50 pmMKE-SXM
7h 10m1 stop
Delta Logo
1:50 pm - 10:44 pmSXM-MKE
10h 54m1 stop
$967Delta
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Mon, Dec 22 - Tue, Dec 30
Delta Logo
5:40 am - 2:50 pmMKE-SXM
7h 10m1 stop
Delta Logo
1:50 pm - 7:58 pmSXM-MKE
8h 08m1 stop
$1,054Delta
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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 American Airlines ($635) and United Airlines ($637).

Good to know

Low seasonSeptember
Cheapest flight$303
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 15% 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.
7.9
DeltaOverall score based on 7957 reviews
7.9Entertainment
7.3Food
7.9Comfort
8.2Boarding
8.5Crew
Airline reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

8.0 ExcellentTarun, Sep 2025MCO - LHR
Read more Delta reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

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

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