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$226+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Mar 9 — Mar 161
Mon 3/9
Mon 3/16
1 adult, Economy
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Cheap 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 February 7, 2026.

This Delta deal was found by Cheapflights users on 2/6. 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 4/231:35 pm
SXM
-
MDW
1 stop9h 53m
Delta
Sun 5/36:00 am
MDW
-
SXM
1 stop7h 05m
Delta
Deal found 2/6$566
This Southwest deal was found by Cheapflights users on 2/6. 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.
Thu 4/232:35 pm
SXM
-
MDW
2 stops23h 10m
Southwest
Sun 5/38:55 pm
MDW
-
SXM
2 stops15h 45m
Southwest
Deal found 2/6$580
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 3/273:20 pm
SXM
-
MDW
1 stop21h 30m
Multiple Airlines
Fri 4/34:15 pm
MDW
-
SXM
2 stops17h 40m
Multiple Airlines
Deal found 2/6$715
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2212:55 pm
SXM
-
MDW
1 stop10h 36m
Delta
Sun 3/296:00 am
MDW
-
SXM
1 stop6h 54m
Delta
Deal found 2/5$1,362
This WestJet deal was found by Cheapflights users on 2/6. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/273:20 pm
SXM
-
MDW
2 stops23h 05m
WestJet
Fri 4/39:35 am
MDW
-
SXM
2 stops51h 42m
WestJet
Deal found 2/6$3,242

Find 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 February 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$566
(Delta)

One-way from

$226
(Kiwi.com)
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
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From St. Maarten to Chicago Midway
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One-way flight from St. Maarten to Chicago Midway
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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 February 7, 2026.
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 4/23

2:35 pm-12:45 pm

2 stops23h 10m

Chicago Midway

Sun 5/3

8:55 pm-1:40 pm

2 stops15h 45m

$580

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/27

3:20 pm-11:50 am

1 stop21h 30m

Chicago Midway

Fri 4/3

4:15 pm-10:55 am

2 stops17h 40m

$715

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 3/22

12:55 pm-10:31 pm

1 stop10h 36m

Chicago Midway

Sun 3/29

6:00 am-1:54 pm

1 stop6h 54m

$1,362

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/27

3:20 pm-1:25 pm

2 stops23h 05m

Chicago Midway

Fri 4/3

9:35 am-2:17 pm

2 stops51h 42m

$3,242

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 2/19

3:20 pm-10:25 pm

2 stops33h 05m

$226

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 5/12

2:11 pm-1:00 pm

2 stops23h 49m

$250

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/23

2:11 pm-1:00 pm

2 stops23h 49m

$254

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/23

2:35 pm-11:40 pm

1 stop10h 05m

$332

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 5/25

2:35 pm-11:40 pm

1 stop10h 05m

$367

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 2/19

1:38 pm-10:31 pm

1 stop10h 53m

$478

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 13 results
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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 10h 36m. St. Maarten and Chicago Midway Airport are separated by a distance of 2189 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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