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$231+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$603
(Delta)

One-way from

$231
(Trip.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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/11. 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 9/223:20 pmSXM - MDW
2 stops18h 20mDelta
Mon 9/296:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 8/11$603
This Delta deal was found by Cheapflights users on 8/11. 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 9/203:20 pmSXM - MDW
2 stops18h 20mDelta
Sat 9/2711:00 amMDW - SXM
1 stop25h 50mDelta
Deal found 8/11$829
This Delta deal was found by Cheapflights users on 8/13. 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 9/63:21 pmSXM - MDW
2 stops18h 14mDelta
Sat 9/136:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 8/13$843

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 August 14, 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

Mon 9/22

3:20 pm-8:40 am

2 stops18h 20m

Chicago Midway

Mon 9/29

6:00 am-1:50 pm

1 stop6h 50m

$603

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/20

3:20 pm-8:40 am

2 stops18h 20m

Chicago Midway

Sat 9/27

11:00 am-1:50 pm

1 stop25h 50m

$829

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/6

3:21 pm-8:35 am

2 stops18h 14m

Chicago Midway

Sat 9/13

6:00 am-1:50 pm

1 stop6h 50m

$843

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/20

3:05 pm-9:18 am

2 stops19h 13m

$231

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/6

4:28 pm-8:24 pm

2 stops29h 56m

$331

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 11/9

4:20 pm-10:05 am

1 stop19h 45m

$366

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/6

4:00 pm-9:44 pm

1 stop7h 44m

$485

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 12/7

4:00 pm-9:44 pm

1 stop7h 44m

$640

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/5

1:45 pm-9:46 pm

1 stop10h 01m

$1,268

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 12/7

4:20 pm-6:07 pm

2 stops27h 47m

$1,627

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

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.

  • 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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