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Midway

$169+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$453
(Delta)

One-way from

$169
(Trip.com)

Popular in

April

Cheapest in

June

Average price

$408
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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 9/1912:40 pmYWG - MDW
1 stop5h 27mDelta
Tue 9/231:00 pmMDW - YWG
2 stops10h 32mDelta
Deal found 6/11$453
This oojo deal was found by Cheapflights users on 6/10. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/259:00 amYWG - MDW
1 stop12h 42mWestJet
Mon 7/286:20 pmMDW - YWG
2 stops19h 23mWestJet
Deal found 6/10$489
This Mytrip deal was found by Cheapflights users on 6/9. 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.
Mon 6/2311:45 amYWG - MDW
2 stops21h 00mPorter Airlines
Mon 6/305:50 pmMDW - YWG
2 stops28h 56mPorter Airlines
Deal found 6/9$497
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/912:26 pmYWG - MDW
1 stop5h 13mMultiple Airlines
Mon 7/145:20 pmMDW - YWG
2 stops29h 26mMultiple Airlines
Deal found 6/12$606

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 June 12, 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 9/19

12:40 pm-6:07 pm

1 stop5h 27m

Chicago Midway

Tue 9/23

1:00 pm-11:32 pm

2 stops10h 32m

$453

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 7/25

9:00 am-9:42 pm

1 stop12h 42m

Chicago Midway

Mon 7/28

6:20 pm-1:43 pm

2 stops19h 23m

$489

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 6/23

11:45 am-8:45 am

2 stops21h 00m

Chicago Midway

Mon 6/30

5:50 pm-10:46 pm

2 stops28h 56m

$497

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 8/24

11:45 am-4:24 pm

2 stops28h 39m

Chicago Midway

Sun 8/31

9:40 am-10:46 pm

2 stops13h 06m

$571

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 8/13

5:10 pm-8:45 am

1 stop15h 35m

$249

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 7/25

8:35 am-5:39 pm

1 stop9h 04m

$280

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 8/1

9:00 am-9:45 am

1 stop24h 45m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 2025.
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

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
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

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
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

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
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Crew

8.7

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.

  • 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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