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$352+ Cheap flights from Saint Martin Island 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap flight deals from Saint Martin Island to Midway

Keep the following information in mind while searching for Saint Martin Island to Midway flight deals. Data was last updated September 29, 2025.

Round-trip from

$663
(Delta)

One-way from

$352
(Kiwi.com)
From Saint Martin Island to Chicago Midway
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One-way flight from Saint Martin Island to Chicago Midway
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Find flight deals from Saint Martin Island to Midway

Cheapest flights from Saint Martin Island to Midway
Explore the most affordable flight options available from Saint Martin Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Delta deal was found by Cheapflights users on 9/29. 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.
Sun 11/234:20 pmSXM - MDW
1 stop9h 20mDelta
Sun 11/306:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 9/29$663
This Delta deal was found by Cheapflights users on 9/29. 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.
Sun 10/263:14 pmSXM - MDW
1 stop8h 00mDelta
Sun 11/25:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/29$883
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Sun 11/234:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 11/307:02 pmMDW - SXM
2 stops42h 19mMultiple Airlines
Deal found 9/29$1,143

Cheapflights Fare Finder

 
Customize your flight search to find flights from Saint Martin Island 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 29, 2025.
Use the filters below to find and compare flights from Saint Martin Island to Chicago Midway Airport that are best for you.

Fly from

Saint Martin Island

Fly to

Midway

Route

Depart

Return

Price

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 11/23

4:20 pm-11:40 pm

1 stop9h 20m

Chicago Midway

Sun 11/30

6:00 am-2:55 pm

1 stop6h 55m

$663

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

1:00 pm-11:15 am

2 stops21h 15m

$697

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 11/23

4:20 pm-10:05 am

1 stop19h 45m

Chicago Midway

Sun 11/30

7:02 pm-3:21 pm

2 stops42h 19m

$1,143

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-7:11 am

2 stops17h 06m

$352

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 10/5

8:35 pm-1:38 pm

3 stops42h 03m

$390

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 10/5

2:10 pm-10:14 pm

2 stops33h 04m

$605

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/5

1:45 pm-9:46 pm

1 stop10h 01m

$1,328

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/13

3:25 pm-11:32 pm

1 stop10h 07m

$2,716

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Best time to book a flight from Saint Martin Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Saint Martin Island 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 Saint Martin Island 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 Saint Martin Island 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 Saint Martin Island to Chicago Midway Airport?

    A quick flight from Saint Martin Island to Chicago Midway Airport can take about 9h 20m. Delta provides one of the quickest options available for as low as $663. Saint Martin Island and Chicago Midway Airport are separated by a distance of 2189 mi.

  • Can I find deals for flights from Saint Martin Island to Midway that include hotel bookings?

    Yes. In addition to deals on Saint Martin Island to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Saint Martin Island to Midway?

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

  • Can I find deals for business class flights from Saint Martin Island to Midway?

    Yes. Cheapflights offers flight deals from Saint Martin Island 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 Saint Martin Island to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Saint Martin Island to Chicago Midway Airport (average of $160). Flying from Saint Martin Island 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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