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$248+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
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 November 21, 2025.

Round-trip from

$368
(Delta)

One-way from

$248
(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 November 21, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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 12/63:25 pmSXM - MDW
1 stop10h 22mDelta
Sat 12/136:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 11/19$368
This Delta deal was found by Cheapflights users on 11/18. 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.
Fri 12/123:53 pmSXM - MDW
1 stop9h 54mDelta
Sun 12/146:00 amMDW - SXM
1 stop6h 28mDelta
Deal found 11/18$377
This Mytrip deal was found by Cheapflights users on 11/19. 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 12/65:00 pmSXM - MDW
2 stops22h 10mMultiple Airlines
Sat 12/131:50 pmMDW - SXM
2 stops23h 31mMultiple Airlines
Deal found 11/19$1,570

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 November 21, 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

Sat 12/6

3:25 pm-11:47 pm

1 stop10h 22m

Chicago Midway

Sat 12/13

6:00 am-2:50 pm

1 stop6h 50m

$368

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 12/12

3:53 pm-11:47 pm

1 stop9h 54m

Chicago Midway

Sun 12/14

6:00 am-2:28 pm

1 stop6h 28m

$377

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/6

5:00 pm-1:10 pm

2 stops22h 10m

Chicago Midway

Sat 12/13

1:50 pm-3:21 pm

2 stops23h 31m

$1,570

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 12/22

3:20 pm-9:58 pm

2 stops32h 38m

$248

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 12/22

1:45 pm-10:22 pm

1 stop10h 37m

$335

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/5

3:20 pm-10:17 pm

2 stops32h 57m

$415

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/13

3:25 pm-11:47 pm

1 stop10h 22m

$485

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/20

12:45 pm-9:46 pm

1 stop10h 01m

$555

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/5

1:55 pm-10:07 pm

1 stop10h 12m

$931

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

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 10h 22m. Delta provides one of the quickest options available for as low as $368. 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.

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
Hammond
Porter
Benton Harbor
Merrillville

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