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St. Maarten

$179+ Cheap flights from Midway (MDW) to St. Maarten

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Aug 25 — Sep 11
Tue 8/25
Tue 9/1
1 adult, Economy
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Cheap flight deals from Midway to St. Maarten

Cheapest flights from Midway to St. Maarten
Explore the most affordable flight options available from Midway to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 26, 2026.

This Southwest deal was found by Cheapflights users on 7/23. 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.
Fri 11/275:05 am
MDW
-
SXM
1 stop7h 15m
Southwest
Thu 12/33:20 pm
SXM
-
MDW
2 stops16h 20m
Southwest
Deal found 7/23$448
This Southwest deal was found by Cheapflights users on 7/24. 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.
Fri 9/185:00 am
MDW
-
SXM
1 stop8h 05m
Southwest
Sat 9/261:55 pm
SXM
-
MDW
1 stop8h 05m
Southwest
Deal found 7/24$470
This Southwest deal was found by Cheapflights users on 7/21. 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.
Wed 11/115:15 am
MDW
-
SXM
1 stop7h 05m
Southwest
Wed 11/183:20 pm
SXM
-
MDW
2 stops16h 20m
Southwest
Deal found 7/21$476
This Southwest deal was found by Cheapflights users on 7/22. 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.
Fri 9/115:00 am
MDW
-
SXM
1 stop8h 05m
Southwest
Sat 9/191:55 pm
SXM
-
MDW
1 stop8h 00m
Southwest
Deal found 7/22$495
This Southwest deal was found by Cheapflights users on 7/23. 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.
Wed 9/305:20 pm
MDW
-
SXM
2 stops19h 45m
Southwest
Mon 10/53:05 pm
SXM
-
MDW
2 stops9h 50m
Southwest
Deal found 7/23$498
This Southwest deal was found by Cheapflights users on 7/22. 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.
Sat 8/295:00 am
MDW
-
SXM
1 stop6h 55m
Southwest
Fri 9/43:05 pm
SXM
-
MDW
1 stop8h 35m
Southwest
Deal found 7/22$506
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sun 11/18:25 pm
MDW
-
SXM
2 stops17h 15m
Southwest
Sun 11/83:20 pm
SXM
-
MDW
2 stops10h 45m
Southwest
Deal found 7/23$511
This Southwest deal was found by Cheapflights users on 7/25. 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.
Sat 9/56:15 pm
MDW
-
SXM
2 stops18h 50m
Southwest
Sat 9/121:55 pm
SXM
-
MDW
1 stop8h 05m
Southwest
Deal found 7/25$517

Find flight deals from Midway to St. Maarten

Keep the following information in mind while searching for Midway to St. Maarten flight deals. Data was last updated July 26, 2026.

Round-trip from

$448
(Southwest)

One-way from

$179
(Southwest)

Popular in

June

Cheapest in

January

Average price

$722
From Chicago Midway to St. Maarten
Search Deals
One-way flight from Chicago Midway to St. Maarten
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 July 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 9/30

5:20 pm-2:05 pm

2 stops19h 45m

Simpson Bay Princess Juliana

Mon 10/5

3:05 pm-11:55 pm

2 stops9h 50m

$498

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 9/11

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 9/19

1:55 pm-8:55 pm

1 stop8h 00m

$505

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 8/29

6:00 pm-2:05 pm

2 stops19h 05m

Simpson Bay Princess Juliana

Fri 9/4

3:05 pm-10:40 pm

1 stop8h 35m

$514
Quickest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 9/5

5:00 am-12:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 9/12

1:55 pm-9:00 pm

1 stop8h 05m

$547

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 11/27

6:30 pm-1:30 pm

2 stops17h 00m

Simpson Bay Princess Juliana

Thu 12/3

3:20 pm-5:40 am

2 stops16h 20m

$554

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 10/24

4:05 pm-2:05 pm

2 stops21h 00m

Simpson Bay Princess Juliana

Sat 11/7

3:20 pm-9:40 pm

1 stop8h 20m

$580

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 10/7

1:28 pm-1:49 pm

2 stops23h 21m

Simpson Bay Princess Juliana

Sat 10/24

3:14 pm-10:25 pm

1 stop8h 11m

$670

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 1/15

5:59 pm-4:00 pm

2 stops20h 01m

Simpson Bay Princess Juliana

Sat 1/23

5:25 pm-9:52 am

1 stop18h 27m

$677

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/2

8:55 pm-3:40 pm

2 stops16h 45m

Simpson Bay Princess Juliana

Sat 1/9

2:30 pm-9:20 pm

1 stop8h 50m

$677

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 8/27

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 8/31

3:05 pm-10:40 pm

1 stop8h 35m

$689

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 20 resultsSorted by cheapest first
1
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Best time to book a flight from Midway to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Midway with our price prediction graph.
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 Chicago Midway Airport to St. Maarten

How often are flights from Chicago to St. Maarten delayed?

About 100% of weekly flights between Chicago and St. Maarten have experienced delays in the past year, with the average delay time being 33 minutes.

What is the most punctual flight time for Chicago to St. Maarten flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

Related info for your journey

Find useful and relevant information for your journey from Midway to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to St. Maarten?

    There are many flights that can get you from Chicago Midway Airport to St. Maarten in 19h 45m. Fly via Southwest to get the fastest option. The distance from Chicago Midway Airport to St. Maarten is about 2189 mi.

  • Can I find deals for flights from Midway to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Midway to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to St. Maarten.

  • Can I find deals for business class flights from Midway to St. Maarten?

    Yes. Cheapflights offers flight deals from Midway to St. Maarten by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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