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$277+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
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 January 12, 2026.

Round-trip from

$500
(Delta)

One-way from

$277
(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 January 12, 2026.

This Delta deal was found by Cheapflights users on 1/11. 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.
Tue 2/101:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Tue 2/176:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Deal found 1/11$500
This Delta deal was found by Cheapflights users on 1/12. 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 1/311:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Sat 2/76:25 am
MDW
-
SXM
1 stop7h 38m
Delta
Deal found 1/12$560
This Delta deal was found by Cheapflights users on 1/10. 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 1/241:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Sat 1/316:25 am
MDW
-
SXM
1 stop7h 38m
Delta
Deal found 1/10$600
This Delta deal was found by Cheapflights users on 1/12. 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 5/83:20 pm
SXM
-
MDW
2 stops22h 10m
Delta
Sun 5/175:59 pm
MDW
-
SXM
2 stops19h 00m
Delta
Deal found 1/12$620
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/254:20 pm
SXM
-
MDW
1 stop19h 50m
Multiple Airlines
Sun 2/14:15 pm
MDW
-
SXM
2 stops17h 40m
Multiple Airlines
Deal found 1/11$640
This Southwest deal was found by Cheapflights users on 1/12. 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.
Mon 5/112:35 pm
SXM
-
MDW
1 stop10h 05m
Southwest
Wed 5/206:00 am
MDW
-
SXM
1 stop6h 40m
Southwest
Deal found 1/12$645
This Delta deal was found by Cheapflights users on 1/11. 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 1/171:55 pm
SXM
-
MDW
1 stop10h 12m
Delta
Sat 1/246:25 am
MDW
-
SXM
1 stop7h 38m
Delta
Deal found 1/11$720
This Delta deal was found by Cheapflights users on 1/11. 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.
Sun 1/251:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Sun 2/16:00 am
MDW
-
SXM
1 stop6h 55m
Delta
Deal found 1/11$793
This Delta deal was found by Cheapflights users on 1/12. 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 2/261:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Thu 3/56:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Deal found 1/12$1,277

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 January 12, 2026.
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 1/31

1:55 pm-10:22 pm

1 stop10h 27m

Chicago Midway

Sat 2/7

6:25 am-4:03 pm

1 stop7h 38m

$560

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 1/24

1:55 pm-10:22 pm

1 stop10h 27m

Chicago Midway

Sat 1/31

6:25 am-4:03 pm

1 stop7h 38m

$600

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 5/14

3:20 pm-6:31 pm

2 stops28h 11m

Chicago Midway

Mon 5/18

6:00 am-1:59 pm

1 stop6h 59m

$620

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 5/14

3:20 pm-12:30 pm

2 stops22h 10m

Chicago Midway

Sun 5/17

5:59 pm-1:59 pm

2 stops19h 00m

$620

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-12:30 pm

2 stops22h 10m

Chicago Midway

Sun 5/17

6:00 am-1:59 pm

1 stop6h 59m

$620

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 5/13

3:20 pm-6:31 pm

2 stops28h 11m

Chicago Midway

Sun 5/17

6:00 am-1:59 pm

1 stop6h 59m

$620

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 5/8

3:20 pm-8:42 am

2 stops18h 22m

Chicago Midway

Mon 5/18

6:00 am-1:59 pm

1 stop6h 59m

$620

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 5/13

3:20 pm-6:31 pm

2 stops28h 11m

Chicago Midway

Mon 5/18

6:00 am-1:59 pm

1 stop6h 59m

$620

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 5/12

3:20 pm-12:30 pm

2 stops22h 10m

Chicago Midway

Mon 5/18

6:00 am-1:59 pm

1 stop6h 59m

$620

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 1/25

4:20 pm-10:10 am

1 stop19h 50m

Chicago Midway

Sun 2/1

4:15 pm-11:55 am

2 stops17h 40m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 15 results
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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 27m. Delta provides one of the quickest options available for as low as $560. 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
Merrillville
Hammond
Porter
Benton Harbor

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