$415+ Cheap flights from Milwaukee (MKE) to St. Maarten
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Apr 29 — May 61
Round-trip
1 adult, Economy
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Best
Last-minute
One-way
Cheapest flights from Milwaukee to St. MaartenExplore the most affordable flight options available from Milwaukee to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.
Explore the most affordable flight options available from Milwaukee to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.
This American Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:41 pm
MKE
- SXM
2 stops19h 45m
American Airlines
Tue 4/284:35 pm
SXM
- MKE
2 stops20h 57m
American Airlines
Deal found 3/26![American Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:41 pm
MKE
- SXM
2 stops20h 41m
American Airlines
Wed 5/132:21 pm
SXM
- MKE
2 stops24h 02m
American Airlines
Deal found 3/25![American Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:30 am
MKE
- SXM
1 stop7h 00m
Southwest
Wed 5/132:25 pm
SXM
- MKE
1 stop9h 25m
Southwest
Deal found 3/25![Southwest logo]()
$463
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:30 am
MKE
- SXM
1 stop7h 35m
Delta
Fri 4/241:35 pm
SXM
- MKE
1 stop11h 22m
Delta
Deal found 3/26![Delta logo]()
$488
This American Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:17 pm
MKE
- SXM
2 stops21h 25m
American Airlines
Fri 6/122:53 pm
SXM
- MKE
1 stop10h 06m
American Airlines
Deal found 3/25![American Airlines logo]()
$505
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:40 am
MKE
- SXM
1 stop6h 50m
Southwest
Tue 6/22:25 pm
SXM
- MKE
1 stop9h 25m
Southwest
Deal found 3/28![Southwest logo]()
$600
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:45 am
MKE
- SXM
1 stop7h 04m
Delta
Thu 11/124:10 pm
SXM
- MKE
1 stop9h 14m
Delta
Deal found 3/27![Delta logo]()
$625
Best flights from Milwaukee to St. MaartenDiscover carefully curated flight deals from Milwaukee to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 30, 2026.
Discover carefully curated flight deals from Milwaukee to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 30, 2026.
This American Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:41 pm
MKE
- SXM
2 stops19h 45m
American Airlines
Tue 4/284:35 pm
SXM
- MKE
2 stops20h 57m
American Airlines
Deal found 3/26![American Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:30 am
MKE
- SXM
1 stop7h 00m
Southwest
Wed 5/132:25 pm
SXM
- MKE
1 stop9h 25m
Southwest
Deal found 3/25![Southwest logo]()
$463
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:30 am
MKE
- SXM
1 stop7h 35m
Delta
Fri 4/241:35 pm
SXM
- MKE
1 stop11h 22m
Delta
Deal found 3/26![Delta logo]()
$488
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:00 pm
MKE
- SXM
2 stops16h 33m
United Airlines
Tue 6/23:50 pm
SXM
- MKE
2 stops19h 07m
United Airlines
Deal found 3/28![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:41 pm
MKE
- SXM
1 stop17h 40m
American Airlines
Wed 5/132:21 pm
SXM
- MKE
2 stops27h 46m
American Airlines
Deal found 3/25![American Airlines logo]()
$445
This American Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:17 pm
MKE
- SXM
2 stops21h 25m
American Airlines
Fri 6/122:53 pm
SXM
- MKE
1 stop10h 06m
American Airlines
Deal found 3/25![American Airlines logo]()
$505
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:40 am
MKE
- SXM
1 stop6h 50m
Southwest
Tue 6/22:25 pm
SXM
- MKE
1 stop9h 25m
Southwest
Deal found 3/28![Southwest logo]()
$600
Last-minute flights from Milwaukee to St. MaartenDiscover last-minute flight deals from Milwaukee to St. Maarten. Data last updated March 30, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to St. Maarten. Data last updated March 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:00 am
MKE
- SXM
1 stop8h 28m
American Airlines
Sat 4/43:20 pm
SXM
- MKE
1 stop8h 52m
American Airlines
Deal found 3/26![American Airlines logo]()
$925
This United Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:10 am
MKE
- SXM
1 stop10h 39m
United Airlines
Wed 4/153:50 pm
SXM
- MKE
2 stops19h 10m
United Airlines
Deal found 3/25![United Airlines logo]()
$720
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:30 am
MKE
- SXM
1 stop7h 35m
Delta
Fri 4/241:35 pm
SXM
- MKE
1 stop11h 22m
Delta
Deal found 3/26![Delta logo]()
$488
This American Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:41 pm
MKE
- SXM
1 stop17h 30m
American Airlines
Tue 4/284:35 pm
SXM
- MKE
2 stops19h 55m
American Airlines
Deal found 3/26![American Airlines logo]()
$415
One-way flights from Milwaukee to St. MaartenSearch for one-way flight options from Milwaukee to St. Maarten. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
Search for one-way flight options from Milwaukee to St. Maarten. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
This Travelocity deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:32 pm
MKE
- SXM
2 stops23h 23m
Air Canada
Deal found 3/27![Air Canada logo]()
$960
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:35 am
MKE
- SXM
3 stops24h 20m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$1,191
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:30 am
MKE
- SXM
1 stop7h 35m
Delta
Deal found 3/27![Delta logo]()
$1,803
Find flight deals from Milwaukee to St. Maarten
Keep the following information in mind while searching for Milwaukee to St. Maarten flight deals. Data was last updated March 30, 2026.
Round-trip from | $415 (American Airlines) |
|---|---|
Popular in | December |
Cheapest in | June |
Average price | $756 |
Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated March 30, 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
Cheapest round-trip
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-12:32 pm
2 stops20h 57m
$415
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Mon 5/4
6:41 pm-1:21 pm
1 stop17h 40m
Simpson Bay Princess Juliana
Wed 5/13
2:21 pm-5:07 pm
2 stops27h 46m
$445
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Mon 5/4
5:30 am-1:30 pm
1 stop7h 00m
Simpson Bay Princess Juliana
Wed 5/13
2:25 pm-10:50 pm
1 stop9h 25m
$463
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Sun 4/19
5:30 am-2:05 pm
1 stop7h 35m
Simpson Bay Princess Juliana
Fri 4/24
1:35 pm-11:57 pm
1 stop11h 22m
$488
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Sat 6/6
5:17 pm-3:42 pm
2 stops21h 25m
Simpson Bay Princess Juliana
Fri 6/12
2:53 pm-11:59 pm
1 stop10h 06m
$505
Quickest round-trip
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Tue 5/26
5:40 am-1:30 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Tue 6/2
2:25 pm-10:50 pm
1 stop9h 25m
$600
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Tue 5/26
7:00 pm-12:33 pm
2 stops16h 33m
Simpson Bay Princess Juliana
Tue 6/2
3:50 pm-9:57 am
2 stops19h 07m
$630
Cheapest one-way
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Fri 4/17
2:32 pm-2:55 pm
2 stops23h 23m
$960
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Fri 4/17
9:35 am-10:55 am
3 stops24h 20m
$1,191
Quickest one-way
MilwaukeeSimpson Bay
MKE - SXM
MKESXM
Milwaukee-Mitchell
Fri 4/17
5:30 am-2:05 pm
1 stop7h 35m
$1,803
Sorted by cheapest first
Best time to book a flight from Milwaukee to St. Maarten
Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Milwaukee with our price prediction graph.
MKE-SXM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to St. Maarten
MKE-SX0
MKE-SXM
What is the cheapest month to book a flight from Milwaukee to St. Maarten?
Currently, February is the cheapest month in which you can book a flight from Milwaukee to St. Maarten (average of $231). Flying from Milwaukee to St. Maarten in June is currently the most expensive (average of $595). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing St. Maarten
Get insights into the airlines that provide service to St. Maarten. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St. Maarten. Reviews last updated March 30, 2026.
Get a feel of what it's like to fly with Delta and American Airlines from Milwaukee to St. Maarten by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Entertainment
7.8
Comfort
7.9
Food
7.2
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Comfort
7.9
Food
7.2
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Comfort
7.9
Food
7.2
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Milwaukee to St. Maarten
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Complete your trip
Complete your trip to St. Maarten by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Milwaukee to St. Maarten, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and St. Maarten flights
Browse other Milwaukee and St. Maarten flight options. Last updated on March 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Milwaukee to St. Maarten
Discover the top 2 airlines that operate flights from Milwaukee to St. Maarten. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$605 | Average$717 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$612 | Average$737 | FlexibilityNo cancel fee | On-timeN/A |