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Cheap flights from Milwaukee to St. Maarten from $498

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to St. Maarten departing on 4/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Milwaukee to St. Maarten

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:29 pm - 1:20 pm
MKE
-
SXM
18h 51m
2 stops
American Airlines Logo
2:24 pm - 9:57 pm
SXM
-
MKE
8h 33m
1 stop
$498American Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
5:29 pm - 1:21 pm
MKE
-
SXM
18h 52m
1 stop
American Airlines Logo
2:24 pm - 9:57 pm
SXM
-
MKE
8h 33m
1 stop
$502American Airlines
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
5:00 am - 2:25 pm
MKE
-
SXM
8h 25m
1 stop
Southwest Logo
3:20 pm - 11:45 pm
SXM
-
MKE
9h 25m
1 stop
$504Southwest
Sun, Apr 19 - Sun, Apr 26
American Airlines Logo
6:41 pm - 1:21 pm
MKE
-
SXM
17h 40m
1 stop
American Airlines Logo
2:24 pm - 10:47 pm
SXM
-
MKE
9h 23m
1 stop
$518American Airlines
Mon, May 4 - Mon, May 11
American Airlines Logo
5:41 pm - 2:26 pm
MKE
-
SXM
19h 45m
2 stops
American Airlines Logo
4:35 pm - 11:30 am
SXM
-
MKE
19h 55m
2 stops
$523American Airlines
Fri, Apr 24 - Tue, Apr 28
American Airlines Logo
5:41 pm - 3:22 pm
MKE
-
SXM
20h 41m
2 stops
American Airlines Logo
4:35 pm - 1:23 pm
SXM
-
MKE
21h 48m
2 stops
$579American Airlines
Sun, Apr 19 - Sun, Apr 26
American Airlines Logo
6:41 pm - 1:11 pm
MKE
-
SXM
17h 30m
1 stop
American Airlines Logo
2:24 pm - 9:57 pm
SXM
-
MKE
8h 33m
1 stop
$594American Airlines
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
5:10 am - 2:00 pm
MKE
-
SXM
7h 50m
1 stop
Southwest Logo
3:00 pm - 10:45 pm
SXM
-
MKE
8h 45m
1 stop
$600Southwest
Wed, Jul 8 - Wed, Jul 15
American Airlines Logo
6:41 pm - 1:11 pm
MKE
-
SXM
17h 30m
1 stop
American Airlines Logo
2:24 pm - 9:57 pm
SXM
-
MKE
8h 33m
1 stop
$604American Airlines
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
5:00 am - 2:35 pm
MKE
-
SXM
8h 35m
1 stop
Southwest Logo
3:35 pm - 9:50 am
SXM
-
MKE
19h 15m
2 stops
$605Southwest
Sun, Jun 14 - Sun, Jun 21

American Airlines flights from Milwaukee to St. Maarten

Our best American Airlines deals on Milwaukee to St. Maarten flight tickets
American Airlines
Apr 7
MKE5:29 pmMilwaukee-Mitchell
18h 51m
2 stops
SXM1:20 pmSimpson Bay Princess Juliana
Apr 14
SXM2:24 pmSimpson Bay Princess Juliana
8h 33m
1 stop
MKE9:57 pmMilwaukee-Mitchell
$498
American Airlines
Apr 7
MKE5:29 pmMilwaukee-Mitchell
18h 52m
1 stop
SXM1:21 pmSimpson Bay Princess Juliana
Apr 14
SXM2:24 pmSimpson Bay Princess Juliana
8h 33m
1 stop
MKE9:57 pmMilwaukee-Mitchell
$502
American Airlines
May 4
MKE6:41 pmMilwaukee-Mitchell
17h 40m
1 stop
SXM1:21 pmSimpson Bay Princess Juliana
May 11
SXM2:24 pmSimpson Bay Princess Juliana
9h 23m
1 stop
MKE10:47 pmMilwaukee-Mitchell
$518

JetBlue flights from Milwaukee to St. Maarten

Our best JetBlue deals on Milwaukee to St. Maarten flight tickets
JetBlue
May 2
MKE5:09 pmMilwaukee-Mitchell
19h 19m
2 stops
SXM1:28 pmSimpson Bay Princess Juliana
May 9
SXM12:30 pmSimpson Bay Princess Juliana
28h 09m
2 stops
MKE3:39 pmMilwaukee-Mitchell
$1,280
JetBlue
May 2
MKE5:09 pmMilwaukee-Mitchell
18h 25m
2 stops
SXM12:34 pmSimpson Bay Princess Juliana
May 9
SXM12:30 pmSimpson Bay Princess Juliana
28h 09m
2 stops
MKE3:39 pmMilwaukee-Mitchell
$1,299

momondo Fare Finder

 
Customize your flight search to find flights from Milwaukee to St. Maarten that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 9, 2026.
Use the filters below to find and compare flights from Milwaukee to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 4/7

5:29 pm-1:20 pm

2 stops18h 51m

Simpson Bay Princess Juliana

Tue 4/14

2:24 pm-9:57 pm

1 stop8h 33m

$498

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Tue 4/7

5:29 pm-1:21 pm

1 stop18h 52m

Simpson Bay Princess Juliana

Tue 4/14

2:24 pm-9:57 pm

1 stop8h 33m

$502

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 4/19

5:00 am-2:25 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Sun 4/26

3:20 pm-11:45 pm

1 stop9h 25m

$504

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Mon 5/4

6:41 pm-1:21 pm

1 stop17h 40m

Simpson Bay Princess Juliana

Mon 5/11

2:24 pm-10:47 pm

1 stop9h 23m

$518

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

5:41 pm-2:26 pm

2 stops19h 45m

Simpson Bay Princess Juliana

Tue 4/28

4:35 pm-11:30 am

2 stops19h 55m

$523

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 4/19

5:41 pm-3:22 pm

2 stops20h 41m

Simpson Bay Princess Juliana

Sun 4/26

4:35 pm-1:23 pm

2 stops21h 48m

$579

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:41 pm-1:11 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Tue 4/28

2:24 pm-9:57 pm

1 stop8h 33m

$594
Quickest round-trip

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Wed 7/8

5:10 am-2:00 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Wed 7/15

3:00 pm-10:45 pm

1 stop8h 45m

$600

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Fri 4/24

6:41 pm-1:11 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Tue 4/28

2:24 pm-9:57 pm

1 stop8h 33m

$604

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sun 6/14

5:00 am-2:35 pm

1 stop8h 35m

Simpson Bay Princess Juliana

Sun 6/21

3:35 pm-9:50 am

2 stops19h 15m

$605

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to St. Maarten from

How to get the cheapest flight ticket from Milwaukee to St. Maarten

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What airlines fly to St. Maarten?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to St. Maarten from Milwaukee according to our data. American Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to St. Maarten. Keep in mind that there are 6 different airlines that fly to St. Maarten on a routine basis, so you have a few additional options to choose from.

Cheap Milwaukee to St. Maarten flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milwaukee to St. Maarten

Fastest flight time

7h 09m

Direct flights

None
The fastest flight from Milwaukee to St. Maarten takes 7h 09m
There are no direct flights from Milwaukee to St. Maarten. There are no popular flight routes from Milwaukee to St. Maarten.
Search flight deals

  • When did momondo last update prices for flights from Milwaukee-Mitchell Airport to St. Maarten?

    Prices for flights from Milwaukee-Mitchell Airport to St. Maarten are updated daily.

  • How many operators does momondo search for flights from Milwaukee-Mitchell Airport to St. Maarten?

  • How old do you have to be to fly from Milwaukee-Mitchell Airport to St. Maarten?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milwaukee-Mitchell Airport to St. Maarten.

  • What documentation or ID do you need to fly to St. Maarten?

    The travel and health documents required for your trip to St. Maarten can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at St. Maarten. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Milwaukee to St. Maarten

Compare and see reviews for airlines that fly from Milwaukee to St. Maarten with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $605Free CancellationRating
7.1
11,403 reviews
Search American Airlines flights
DeltaPriceFrom $612Free CancellationRating
7.9
8,272 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Milwaukee to St. Maarten?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Milwaukee to St. Maarten for you.

Can I find flights from Milwaukee to St. Maarten with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to St. Maarten from Milwaukee with this policy.

How can momondo help me find flights from Milwaukee to St. Maarten?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to St. Maarten from Milwaukee.

I’m not ready to book a flight from Milwaukee to St. Maarten right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Milwaukee to St. Maarten flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Wed 4/8
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Popular cities in St. Maarten

Popular flights according to clicks in the last 7 days on momondo
Flights to Simpson Bayfrom $235