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$230+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$592
(Delta)

One-way from

$230
(Gotogate)
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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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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 12/14:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 12/76:37 pmMDW - SXM
2 stops17h 38mMultiple Airlines
Deal found 10/29$603
This Delta deal was found by Cheapflights users on 10/30. 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 12/113:53 pmSXM - MDW
1 stop9h 54mDelta
Thu 12/186:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 10/30$627
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 12/154:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Mon 12/228:15 amMDW - SXM
2 stops52h 00mMultiple Airlines
Deal found 10/29$659
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/114:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Thu 12/186:12 amMDW - SXM
2 stops30h 03mMultiple Airlines
Deal found 10/30$660
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/14:20 pmSXM - MDW
1 stop19h 34mDelta
Sun 12/76:00 amMDW - SXM
1 stop6h 28mDelta
Deal found 10/29$727
This Delta deal was found by Cheapflights users on 10/29. 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 11/223:30 pmSXM - MDW
1 stop10h 10mDelta
Sat 11/296:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 10/29$757
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/223:40 pmSXM - MDW
3 stops23h 27mMultiple Airlines
Sat 11/291:47 pmMDW - SXM
2 stops23h 34mMultiple Airlines
Deal found 10/30$979

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 October 30, 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

Fri 3/6

4:26 pm-3:25 pm

2 stops24h 59m

Chicago Midway

Tue 3/10

9:30 am-11:15 am

2 stops24h 45m

$592

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 12/11

3:53 pm-11:47 pm

1 stop9h 54m

Chicago Midway

Thu 12/18

6:00 am-2:50 pm

1 stop6h 50m

$627

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 12/15

4:20 pm-10:05 am

1 stop19h 45m

Chicago Midway

Mon 12/22

8:15 am-2:15 pm

2 stops52h 00m

$659

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 12/1

4:20 pm-9:54 am

1 stop19h 34m

Chicago Midway

Sun 12/7

6:00 am-2:28 pm

1 stop6h 28m

$727

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 11/22

3:30 pm-11:40 pm

1 stop10h 10m

Chicago Midway

Sat 11/29

6:00 am-2:55 pm

1 stop6h 55m

$757

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 12/11

4:20 pm-3:20 pm

1 stop25h 00m

Chicago Midway

Thu 12/18

4:15 pm-3:21 pm

1 stop21h 06m

$909

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 11/22

3:40 pm-1:07 pm

3 stops23h 27m

Chicago Midway

Sat 11/29

1:47 pm-3:21 pm

2 stops23h 34m

$979

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/13

2:40 pm-6:12 pm

1 stop29h 32m

$230

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 12/15

3:20 pm-8:46 am

2 stops43h 26m

$235

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/13

3:20 pm-6:12 pm

2 stops28h 52m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 18 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 24h 59m. 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.

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
Porter
Benton Harbor

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Alternative routes for St. Maarten to Midway

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