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$163+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$306
(Kiwi.com)

One-way from

$163
(Kiwi.com)

Popular in

August

Cheapest in

June

Average price

$477
Provider with most accurate pricing for Winnipeg-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Winnipeg-Chicago Midway flights.
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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. 7% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/309:00 amYWG - MDW
1 stop13h 14mMultiple Airlines
Fri 6/66:30 amMDW - YWG
1 stop9h 58mMultiple Airlines
Deal found 4/15$306
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1212:40 pmYWG - MDW
1 stop5h 23mDelta
Wed 7/161:00 pmMDW - YWG
2 stops10h 22mDelta
Deal found 4/15$371
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/3011:25 amYWG - MDW
2 stops21h 20mPorter Airlines
Fri 6/69:40 amMDW - YWG
2 stops13h 06mPorter Airlines
Deal found 4/15$438
This WestJet deal was found by Cheapflights users on 4/15. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/108:35 amYWG - MDW
1 stop9h 05mWestJet
Tue 6/1712:44 pmMDW - YWG
2 stops11h 47mWestJet
Deal found 4/15$477

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 April 15, 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 5/30

9:00 am-10:14 pm

1 stop13h 14m

Chicago Midway

Fri 6/6

6:30 am-4:28 pm

1 stop9h 58m

$306

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 7/12

12:40 pm-6:03 pm

1 stop5h 23m

Chicago Midway

Wed 7/16

1:00 pm-11:22 pm

2 stops10h 22m

$371

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 5/30

11:25 am-8:45 am

2 stops21h 20m

Chicago Midway

Fri 6/6

9:40 am-10:46 pm

2 stops13h 06m

$438

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 6/10

6:30 am-5:40 pm

2 stops11h 10m

Chicago Midway

Tue 6/17

12:44 pm-12:31 am

2 stops11h 47m

$477

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 5/6

8:15 pm-11:26 am

2 stops15h 11m

$163

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 7/12

6:40 am-12:30 pm

2 stops5h 50m

$239

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 7/12

12:40 pm-6:03 pm

1 stop5h 23m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Compare providers for flights from Winnipeg to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Midway in April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Winnipeg-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 15, 2025.
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.7

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.7

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Delta
8.0
Very good
7,918 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.7

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
WestJet
7.2
Good
2,805 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.7

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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 flying from Winnipeg to Chicago Midway Airport round-trip?

    Delta, at $371, was found to be the cheapest airline from Winnipeg to Chicago Midway Airport.Alternate airlines to your destination round-trip include Porter Airlines and WestJet.

  • 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?

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Merrillville
Hammond
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Valparaiso
Chesterton

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