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$188+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$301
(Kiwi.com)

One-way from

$188
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$448
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. 4% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Thu 9/119:00 amYWG - MDW
1 stop6h 58mMultiple Airlines
Thu 9/186:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
Deal found 8/14$301
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Thu 9/49:00 amYWG - MDW
1 stop6h 58mMultiple Airlines
Sun 9/76:20 amMDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 8/14$326
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/269:00 amYWG - MDW
1 stop14h 20mMultiple Airlines
Wed 10/19:00 amMDW - YWG
2 stops29h 13mMultiple Airlines
Deal found 8/14$343
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:40 amYWG - MDW
2 stops11h 57mDelta
Mon 9/87:17 pmMDW - YWG
1 stop4h 10mDelta
Deal found 8/14$344
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sat 10/1811:20 amYWG - MDW
2 stops21h 19mMultiple Airlines
Thu 10/236:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
Deal found 8/14$349
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 9/278:35 amYWG - MDW
1 stop4h 28mDelta
Sat 10/49:20 amMDW - YWG
1 stop7h 30mDelta
Deal found 8/13$359

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 August 14, 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 9/11

9:00 am-3:58 pm

1 stop6h 58m

Chicago Midway

Thu 9/18

6:20 am-4:22 pm

1 stop10h 02m

$301

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 9/4

9:00 am-3:58 pm

1 stop6h 58m

Chicago Midway

Sun 9/7

6:20 am-12:30 am

2 stops18h 10m

$326

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 9/26

9:00 am-11:20 pm

1 stop14h 20m

Chicago Midway

Wed 10/1

9:00 am-2:13 pm

2 stops29h 13m

$343

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 9/6

6:40 am-6:37 pm

2 stops11h 57m

Chicago Midway

Mon 9/8

7:17 pm-11:27 pm

1 stop4h 10m

$344

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 9/27

8:35 am-5:35 pm

1 stop9h 00m

Chicago Midway

Sat 10/4

1:08 pm-11:27 pm

2 stops10h 19m

$344

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 10/18

11:20 am-8:39 am

2 stops21h 19m

Chicago Midway

Thu 10/23

6:20 am-4:22 pm

1 stop10h 02m

$349

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 10/19

10:45 am-8:39 am

1 stop21h 54m

Chicago Midway

Thu 10/23

9:26 pm-4:22 pm

1 stop18h 56m

$351

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 9/5

9:00 am-8:46 pm

2 stops11h 46m

$188

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 9/15

11:20 am-4:24 pm

2 stops29h 04m

$202

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 9/5

7:00 pm-8:39 am

1 stop13h 39m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 14 results
1
2

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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