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$537+ Cheap flights from St. Maarten to Midway (MDW)

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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from St. Maarten to Midway

Keep the following information in mind while searching for St. Maarten to Midway flight deals. Data was last updated September 16, 2025.

Round-trip from

$600
(Delta)

One-way from

$537
(Kissandfly.com)
From St. Maarten to Chicago Midway
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One-way flight from St. Maarten to Chicago Midway
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Find flight deals from St. Maarten to Midway

Cheapest flights from St. Maarten to Midway
Explore the most affordable flight options available from St. Maarten to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 11/64:14 pmSXM - MDW
2 stops18h 26mDelta
Wed 11/126:48 pmMDW - SXM
2 stops18h 07mDelta
Deal found 9/15$600
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 11/64:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Wed 11/124:15 pmMDW - SXM
1 stop21h 06mMultiple Airlines
Deal found 9/15$668
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 10/263:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 11/211:00 amMDW - SXM
2 stops21h 50mMultiple Airlines
Deal found 9/15$944
This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 10/113:14 pmSXM - MDW
1 stop8h 00mDelta
Fri 10/176:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/14$958
This Delta deal was found by Cheapflights users on 9/15. 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 10/263:14 pmSXM - MDW
1 stop8h 00mDelta
Sun 11/25:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/15$978

Cheapflights Fare Finder

 
Customize your flight search to find flights from St. Maarten to Midway 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 September 16, 2025.
Use the filters below to find and compare flights from St. Maarten to Chicago Midway Airport that are best for you.

Fly from

St. Maarten

Fly to

Midway

Route

Depart

Return

Price

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 11/6

4:14 pm-8:40 am

2 stops18h 26m

Chicago Midway

Wed 11/12

6:48 pm-2:55 pm

2 stops18h 07m

$600

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-6:34 pm

2 stops28h 08m

Chicago Midway

Tue 3/10

5:59 pm-11:15 am

2 stops16h 16m

$697

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 11/6

4:20 pm-10:05 am

1 stop19h 45m

Chicago Midway

Wed 11/12

11:00 am-3:21 pm

1 stop26h 21m

$698

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 11/28

4:20 pm-9:52 am

2 stops43h 32m

$537

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/5

4:28 pm-10:15 pm

2 stops31h 47m

$583

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 1/1

12:25 pm-6:24 pm

3 stops31h 59m

$663

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 1/3

6:10 pm-1:35 pm

2 stops45h 25m

$782

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 1/1

1:50 pm-10:16 pm

1 stop10h 26m

$836

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 11/28

4:20 pm-11:32 pm

1 stop9h 12m

$943

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/5

1:45 pm-9:46 pm

1 stop10h 01m

$1,328

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Best time to book a flight from St. Maarten to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from St. Maarten 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 St. Maarten to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from St. Maarten to Midway. 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 St. Maarten to Chicago Midway Airport?

    Departing from St. Maarten to Chicago Midway Airport will take you 18h 26m. St. Maarten and Chicago Midway Airport are separated by a distance of 2189 mi.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from St. Maarten to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from St. Maarten to Chicago Midway Airport (average of $160). Flying from St. Maarten to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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