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St. Maarten

$150+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
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 June 9, 2026.

This Southwest deal was found by Cheapflights users on 6/7. 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 7/135:10 am
MDW
-
SXM
1 stop7h 15m
Southwest
Tue 7/143:00 pm
SXM
-
MDW
1 stop8h 05m
Southwest
Deal found 6/7$415
This Southwest deal was found by Cheapflights users on 6/7. 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 7/205:10 am
MDW
-
SXM
1 stop7h 15m
Southwest
Wed 7/293:00 pm
SXM
-
MDW
2 stops17h 10m
Southwest
Deal found 6/7$420
This Southwest deal was found by Cheapflights users on 6/4. 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 7/105:10 am
MDW
-
SXM
1 stop7h 15m
Southwest
Tue 7/143:00 pm
SXM
-
MDW
1 stop8h 05m
Southwest
Deal found 6/4$442
This Southwest deal was found by Cheapflights users on 6/7. 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
Fri 9/253:05 pm
SXM
-
MDW
1 stop8h 35m
Southwest
Deal found 6/7$468
This Southwest deal was found by Cheapflights users on 6/8. 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 7/75:10 am
MDW
-
SXM
1 stop7h 50m
Southwest
Tue 7/143:00 pm
SXM
-
MDW
1 stop8h 05m
Southwest
Deal found 6/8$484
This Southwest deal was found by Cheapflights users on 6/7. 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 7/38:50 pm
MDW
-
SXM
2 stops17h 15m
Southwest
Thu 7/92:25 pm
SXM
-
MDW
1 stop8h 00m
Southwest
Deal found 6/7$489
This Southwest deal was found by Cheapflights users on 6/5. 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 12/135:10 am
MDW
-
SXM
1 stop8h 30m
Southwest
Thu 12/173:20 pm
SXM
-
MDW
1 stop9h 35m
Southwest
Deal found 6/5$523
This Southwest deal was found by Cheapflights users on 6/5. 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 12/154:15 pm
MDW
-
SXM
2 stops20h 05m
Southwest
Sat 12/192:30 pm
SXM
-
MDW
2 stops11h 50m
Southwest
Deal found 6/5$528

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 June 9, 2026.

Round-trip from

$415
(Southwest)

One-way from

$150
(Southwest)

Popular in

June

Cheapest in

August

Average price

$792
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 ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 9, 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

Mon 7/13

5:10 am-1:25 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Tue 7/14

3:00 pm-10:05 pm

1 stop8h 05m

$415

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/28

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 9/4

3:05 pm-7:35 am

2 stops17h 30m

$489

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 7/3

8:50 pm-3:05 pm

2 stops17h 15m

Simpson Bay Princess Juliana

Thu 7/9

2:25 pm-7:10 am

2 stops17h 45m

$515

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/28

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 9/5

1:55 pm-8:55 pm

1 stop8h 00m

$532

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 6/26

5:10 am-1:25 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Thu 7/2

2:25 pm-12:40 am

1 stop11h 15m

$567

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 8/15

4:05 pm-2:05 pm

2 stops21h 00m

Simpson Bay Princess Juliana

Sat 8/22

1:55 pm-8:55 pm

1 stop8h 00m

$584

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 10/11

8:40 pm-2:00 pm

2 stops16h 20m

Simpson Bay Princess Juliana

Sat 10/17

2:45 pm-7:25 am

2 stops17h 40m

$602

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 7/20

8:50 pm-2:00 pm

2 stops16h 10m

Simpson Bay Princess Juliana

Sat 7/25

2:15 pm-7:10 am

2 stops17h 55m

$631
Quickest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 9/17

6:05 am-1:50 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Wed 9/23

3:20 pm-10:25 pm

1 stop8h 05m

$670

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 9/18

6:05 am-1:50 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Fri 9/25

3:20 pm-10:25 pm

1 stop8h 05m

$670

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

Showing 1-10 of 19 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 7h 15m. 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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