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$126+ Cheap flights from Winnipeg (YWG) 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Winnipeg to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$218
(Kiwi.com)

One-way from

$126
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$363
From Winnipeg to Chicago Midway
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One-way flight from Winnipeg to Chicago Midway
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Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Winnipeg to Midway

Cheapest flights from Winnipeg to Midway
Explore the most affordable flight options available from Winnipeg to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/309:00 pmYWG - MDW
2 stops21h 39mMultiple Airlines
Thu 11/61:37 pmMDW - YWG
1 stop25h 30mMultiple Airlines
Deal found 9/15$218
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/317:30 amYWG - MDW
1 stop11h 09mMultiple Airlines
Sun 11/25:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 9/15$231
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/179:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
Sun 10/196:20 amMDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 9/14$290
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/279:00 pmYWG - MDW
2 stops14h 38mMultiple Airlines
Thu 11/204:15 pmMDW - YWG
1 stop19h 20mMultiple Airlines
Deal found 9/14$335
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/169:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
Sun 10/197:50 amMDW - YWG
2 stops16h 50mMultiple Airlines
Deal found 9/16$345
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 10/155:10 pmYWG - MDW
1 stop15h 29mMultiple Airlines
Wed 10/228:05 amMDW - YWG
2 stops16h 25mMultiple Airlines
Deal found 9/17$368
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/137:00 pmYWG - MDW
1 stop13h 39mMultiple Airlines
Mon 10/209:35 amMDW - YWG
1 stop24h 06mMultiple Airlines
Deal found 9/15$370
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/49:10 amYWG - MDW
2 stops14h 31mMultiple Airlines
Mon 10/69:35 amMDW - YWG
1 stop9h 50mMultiple Airlines
Deal found 9/15$391

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg 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 17, 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago Midway Airport that are best for you.

Fly from

Winnipeg

Fly to

Midway

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/30

9:00 pm-6:39 pm

2 stops21h 39m

Chicago Midway

Thu 11/6

1:37 pm-3:07 pm

1 stop25h 30m

$218

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/31

4:10 pm-2:57 pm

2 stops22h 47m

Chicago Midway

Sun 11/2

5:20 am-2:07 pm

1 stop8h 47m

$268

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 10/17

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

Sun 10/19

6:20 am-12:30 am

2 stops18h 10m

$290

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 10/16

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

Sun 10/19

7:50 am-12:40 am

2 stops16h 50m

$345

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 10/13

7:00 pm-8:39 am

1 stop13h 39m

Chicago Midway

Mon 10/20

9:35 am-9:41 am

1 stop24h 06m

$370

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 10/4

9:10 am-11:41 pm

2 stops14h 31m

Chicago Midway

Mon 10/6

9:35 am-7:25 pm

1 stop9h 50m

$391

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 10/15

5:10 pm-8:39 am

1 stop15h 29m

Chicago Midway

Wed 10/22

9:35 am-12:13 am

1 stop14h 38m

$407

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 10/27

8:05 pm-10:05 am

1 stop14h 00m

Chicago Midway

Thu 11/20

4:15 pm-11:35 am

1 stop19h 20m

$417

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 10/4

8:35 am-1:03 pm

1 stop4h 28m

Chicago Midway

Mon 10/6

9:20 am-11:30 am

1 stop26h 10m

$421

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 11/21

7:30 am-9:53 am

1 stop26h 23m

Chicago Midway

Mon 11/24

7:02 pm-11:48 am

1 stop16h 46m

$424

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
1
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Best time to book a flight from Winnipeg to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Winnipeg 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.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Chicago Midway?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Chicago Midway. On average, Winnipeg has 0 outbound flights to Chicago Midway per day from 0 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • Can I find deals for flights from Winnipeg to Midway that include hotel bookings?

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

  • How can I find direct flights from Winnipeg to Midway?

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

  • Can I find deals for business class flights from Winnipeg to Midway?

    Yes. Cheapflights offers flight deals from Winnipeg 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 Winnipeg to Chicago Midway Airport?

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