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$179+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$323
(Kiwi.com)

One-way from

$179
(Kiwi.com)

Popular in

April

Cheapest in

June

Average price

$450
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. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/30. 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 8/159:00 amYWG - MDW
1 stop14h 17mMultiple Airlines
Tue 8/199:16 amMDW - YWG
2 stops15h 15mMultiple Airlines
Deal found 6/30$323
This Delta deal was found by Cheapflights users on 7/1. 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 7/266:45 amYWG - MDW
1 stop6h 21mDelta
Sat 8/99:24 amMDW - YWG
1 stop7h 26mDelta
Deal found 7/1$385
This oojo deal was found by Cheapflights users on 7/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:30 amYWG - MDW
2 stops14h 42mWestJet
Mon 8/181:08 pmMDW - YWG
2 stops11h 23mWestJet
Deal found 7/1$412

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 July 1, 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

Fri 8/15

9:00 am-11:17 pm

1 stop14h 17m

Chicago Midway

Tue 8/19

9:16 am-12:31 am

2 stops15h 15m

$323

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 7/26

6:45 am-1:06 pm

1 stop6h 21m

Chicago Midway

Sat 8/9

9:24 am-4:50 pm

1 stop7h 26m

$385

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 8/16

6:30 am-9:12 pm

2 stops14h 42m

Chicago Midway

Mon 8/18

1:08 pm-12:31 am

2 stops11h 23m

$412

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 8/25

6:30 am-11:27 pm

2 stops16h 57m

$179

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 7/19

8:35 am-5:10 pm

1 stop8h 35m

$220

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 8/10

6:30 am-9:42 pm

2 stops15h 12m

$239

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 7/13

11:45 am-8:45 am

2 stops21h 00m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 1, 2025.
Read through reviews of airlines operating flights from Winnipeg to Chicago Midway Airport, such as Porter Airlines, Delta, and WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.7

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.7

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,973 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.7

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,909 reviews
Porter Airlines
8.0
Very good
298 reviews

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.7

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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.

  • What are the cheapest airlines to fly from Winnipeg to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $220 on Delta. Other airlines that offer cheap prices include WestJet from $239 and Porter Airlines from $394 one-way.

  • 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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