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$133+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
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Cheap 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 December 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/147:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Fri 1/23:10 pmMDW - YWG
1 stop10h 16mMultiple Airlines
Deal found 12/7$524
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/147:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Wed 12/318:15 amMDW - YWG
2 stops39h 35mMultiple Airlines
Deal found 12/7$532
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/147:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Sun 12/2811:00 amMDW - YWG
2 stops24h 13mMultiple Airlines
Deal found 12/7$562
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Mon 12/158:00 amYWG - MDW
2 stops24h 46mMultiple Airlines
Fri 1/23:10 pmMDW - YWG
1 stop10h 16mMultiple Airlines
Deal found 12/8$577
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/145:45 pmYWG - MDW
1 stop21h 07mMultiple Airlines
Mon 12/2911:00 amMDW - YWG
1 stop12h 35mMultiple Airlines
Deal found 12/8$578
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Mon 12/158:00 amYWG - MDW
2 stops24h 46mMultiple Airlines
Mon 12/2911:00 amMDW - YWG
1 stop12h 35mMultiple Airlines
Deal found 12/8$580
This Justfly.com deal was found by Cheapflights users on 12/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:45 pmYWG - MDW
1 stop24h 33mWestJet
Tue 12/309:50 amMDW - YWG
1 stop29h 17mWestJet
Deal found 12/7$628

Find 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 December 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$239
(Kiwi.com)

One-way from

$133
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$602
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. 9% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 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

Thu 1/22

9:00 pm-8:43 am

2 stops35h 43m

Chicago Midway

Thu 1/29

5:01 pm-3:07 pm

1 stop22h 06m

$239

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/31

6:15 am-11:42 pm

2 stops17h 27m

Chicago Midway

Wed 4/8

6:00 am-3:09 pm

1 stop9h 09m

$329

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/31

6:15 am-11:42 pm

2 stops17h 27m

Chicago Midway

Fri 4/10

6:00 am-3:09 pm

1 stop9h 09m

$357

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 3/25

6:15 am-11:42 pm

2 stops17h 27m

Chicago Midway

Wed 4/1

6:00 am-3:09 pm

1 stop9h 09m

$368

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/15

5:00 am-12:48 pm

2 stops7h 48m

Chicago Midway

Sun 1/18

6:10 am-3:07 pm

1 stop8h 57m

$396

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

6:40 am-6:37 pm

1 stop11h 57m

Chicago Midway

Sun 3/8

7:20 pm-7:09 pm

2 stops23h 49m

$436

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/31

5:45 pm-6:40 pm

1 stop24h 55m

Chicago Midway

Tue 4/7

10:49 am-3:09 pm

1 stop28h 20m

$440

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/8

8:20 pm-10:10 am

1 stop13h 50m

Chicago Midway

Mon 1/12

6:10 am-12:43 am

2 stops18h 33m

$440

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 2/26

5:00 am-5:37 pm

2 stops12h 37m

Chicago Midway

Sun 3/1

9:50 am-11:01 am

1 stop25h 11m

$449

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 1/22

9:00 pm-8:43 am

2 stops35h 43m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 15 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 December.
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.

  • 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
Merrillville
Hammond
Porter
Benton Harbor

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