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$122+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Dec 9 — Dec 161
Tue 12/9
Tue 12/16
1 adult, Economy
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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 November 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Sun 12/146:15 amMDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 11/9$226
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Wed 12/318:15 amMDW - YWG
2 stops51h 54mMultiple Airlines
Deal found 11/9$377
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/307:30 amYWG - MDW
1 stop15h 03mMultiple Airlines
Sun 12/76:15 amMDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 11/9$420
This WestJet deal was found by Cheapflights users on 11/9. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:45 amYWG - MDW
2 stops11h 33mWestJet
Wed 12/106:40 pmMDW - YWG
2 stops24h 32mWestJet
Deal found 11/9$450
This WestJet deal was found by Cheapflights users on 11/9. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:00 pmYWG - MDW
2 stops12h 54mWestJet
Sat 12/611:05 amMDW - YWG
2 stops13h 36mWestJet
Deal found 11/9$459
This FlightHub deal was found by Cheapflights users on 11/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:45 pmYWG - MDW
1 stop24h 33mWestJet
Sun 12/146:40 pmMDW - YWG
2 stops24h 32mWestJet
Deal found 11/9$480
This Mytrip deal was found by Cheapflights users on 11/9. 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 12/17:50 amYWG - MDW
3 stops29h 20mMultiple Airlines
Sat 12/69:59 amMDW - YWG
2 stops9h 36mMultiple Airlines
Deal found 11/9$518

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 November 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$122
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$426
Provider with most accurate pricing for Winnipeg-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Chicago Midway flights.
Search Deals
From Winnipeg to Chicago Midway
Search Deals
One-way flight from Winnipeg to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 9, 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

Sun 12/7

7:30 am-10:12 pm

1 stop14h 42m

Chicago Midway

Sun 12/14

6:15 am-3:07 pm

1 stop8h 52m

$226

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 1/30

7:30 am-11:25 pm

1 stop15h 55m

Chicago Midway

Mon 2/2

6:00 am-12:36 am

2 stops18h 36m

$260

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 12/24

7:30 am-10:12 pm

1 stop14h 42m

Chicago Midway

Wed 12/31

8:15 am-12:09 pm

2 stops51h 54m

$377

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 12/1

9:00 pm-9:54 am

2 stops12h 54m

Chicago Midway

Sat 12/6

7:02 pm-11:45 am

1 stop16h 43m

$420

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 11/30

7:30 am-10:33 pm

1 stop15h 03m

Chicago Midway

Sun 12/7

6:15 am-3:07 pm

1 stop8h 52m

$420

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 2/1

5:00 am-5:55 pm

2 stops12h 55m

Chicago Midway

Thu 2/5

9:34 am-12:39 am

2 stops15h 05m

$432

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

5:00 am-5:37 pm

2 stops12h 37m

Chicago Midway

Sun 3/8

9:20 am-7:24 pm

2 stops10h 04m

$432

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 4/25

5:00 am-6:31 pm

2 stops13h 31m

Chicago Midway

Thu 4/30

1:00 pm-11:00 pm

2 stops10h 00m

$443

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 12/7

5:45 pm-6:18 pm

1 stop24h 33m

Chicago Midway

Sun 12/14

6:40 pm-7:12 pm

2 stops24h 32m

$480

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 12/14

7:30 am-9:52 am

1 stop26h 22m

$122

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/7

Showing 1-10 of 16 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Winnipeg-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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.

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.

  • How long is the flight from Winnipeg to Chicago Midway Airport?

    There are many flights that can get you from Winnipeg to Chicago Midway Airport in 12h 54m. Fly via WestJet to get the fastest option. The distance from Winnipeg to Chicago Midway Airport is about 722 mi.

  • 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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