$565 Find Cheap Flights from Milwaukee to St. Maarten

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 St. Maarten departing on 2/28. 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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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

Sat, Feb 28 - Sat, Mar 7
United Airlines Logo
5:00 am - 3:57 pm
MKE
-
SXM
8h 57m
1 stop
United Airlines Logo
2:40 pm - 9:50 pm
SXM
-
MKE
9h 10m
1 stop
$565United Airlines
Sat, Feb 28 - Sat, Mar 7
United Airlines Logo
4:00 pm - 1:50 pm
MKE
-
SXM
19h 50m
2 stops
United Airlines Logo
5:00 pm - 11:35 am
SXM
-
MKE
20h 35m
2 stops
$570United Airlines
Mon, Mar 16 - Tue, Mar 31
Delta Logo
5:45 am - 1:54 pm
MKE
-
SXM
7h 09m
1 stop
Delta Logo
12:55 pm - 11:58 pm
SXM
-
MKE
12h 03m
1 stop
$605Delta
Tue, May 26 - Mon, Jun 8
United Airlines Logo
7:00 pm - 2:43 pm
MKE
-
SXM
18h 43m
2 stops
United Airlines Logo
3:50 pm - 10:08 am
SXM
-
MKE
19h 18m
2 stops
$610United Airlines
Sat, Feb 28 - Sat, Mar 7
Delta Logo
7:00 am - 4:00 pm
MKE
-
SXM
7h 00m
1 stop
Delta Logo
5:25 pm - 11:47 pm
SXM
-
MKE
8h 22m
1 stop
$614Delta
Tue, Mar 10 - Fri, Mar 20
American Airlines Logo
6:38 am - 3:28 pm
MKE
-
SXM
7h 50m
1 stop
American Airlines Logo
4:01 pm - 10:01 am
SXM
-
MKE
19h 00m
1 stop
$615American Airlines
Mon, Jun 1 - Wed, Jun 10
American Airlines Logo
6:29 pm - 1:22 pm
MKE
-
SXM
17h 53m
2 stops
American Airlines Logo
2:45 pm - 11:59 pm
SXM
-
MKE
10h 14m
1 stop
$620American Airlines
Sun, Mar 1 - Sun, Mar 8
United Airlines Logo
6:00 am - 3:51 pm
MKE
-
SXM
7h 51m
1 stop
United Airlines Logo
1:20 pm - 10:43 pm
SXM
-
MKE
10h 23m
1 stop
$625United Airlines
Mon, Mar 16 - Mon, Mar 30
Delta Logo
5:45 am - 1:54 pm
MKE
-
SXM
7h 09m
1 stop
Delta Logo
3:20 pm - 12:30 pm
SXM
-
MKE
22h 10m
2 stops
$630Delta
Sat, Apr 25 - Sat, May 2
American Airlines Logo
6:32 pm - 1:21 pm
MKE
-
SXM
17h 49m
1 stop
American Airlines Logo
3:32 pm - 10:47 pm
SXM
-
MKE
8h 15m
1 stop
$640American Airlines
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.

What is the cheapest month to fly from Milwaukee to St. Maarten?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to St. Maarten, 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 St. Maarten is August, when tickets cost $639 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $1,991 and $1,329 respectively.

Good to know

Low seasonApril
Cheapest flight$565
Best time to beat the crowds but there is an average 49% increase in price.
Most popular time to fly and prices are also 4% 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.

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 8128 reviews
7.2Food
8.5Crew
8.1Boarding
7.9Comfort
7.8Entertainment
Airline reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

10.0 ExcellentDr. Simon, Jan 2026
LAX - JFK
Read more Delta reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

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.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

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

Information on your arrival and departure airports