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$123+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
nov. 22 — nov. 291
sáb. 11/22
sáb. 11/29
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 octubre 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
vie. 12/57:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
vie. 12/126:15 amMDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 10/21$234
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
dom. 12/77:30 amYWG - MDW
1 stop10h 42mMultiple Airlines
dom. 12/147:24 pmMDW - YWG
1 stop29h 19mMultiple Airlines
Deal found 10/23$239
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
jue. 11/209:00 pmYWG - MDW
2 stops17h 40mMultiple Airlines
lun. 11/246:20 amMDW - YWG
1 stop18h 23mMultiple Airlines
Deal found 10/21$289
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
mar. 10/289:00 pmYWG - MDW
2 stops15h 41mMultiple Airlines
vie. 10/316:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 10/21$297
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
mar. 10/289:00 pmYWG - MDW
2 stops15h 41mMultiple Airlines
jue. 10/301:37 pmMDW - YWG
1 stop25h 30mMultiple Airlines
Deal found 10/21$302
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
sáb. 12/66:40 amYWG - MDW
1 stop6h 28mMultiple Airlines
sáb. 12/136:00 amMDW - YWG
2 stops18h 41mMultiple Airlines
Deal found 10/22$366
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
jue. 11/139:00 pmYWG - MDW
2 stops21h 39mMultiple Airlines
dom. 11/166:15 amMDW - YWG
1 stop8h 52mMultiple Airlines
Deal found 10/21$380
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
dom. 11/97:30 amYWG - MDW
1 stop14h 33mMultiple Airlines
mié. 11/122:06 pmMDW - YWG
2 stops34h 33mMultiple Airlines
Deal found 10/21$414

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 octubre 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$234
(Kiwi.com)

One-way from

$123
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$373
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. 4% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 23, 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

vie. 12/5

7:30 am-10:12 pm

1 stop14h 42m

Chicago Midway

vie. 12/12

6:15 am-3:07 pm

1 stop8h 52m

$234

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

dom. 12/7

7:30 am-6:12 pm

1 stop10h 42m

Chicago Midway

dom. 12/14

6:15 am-12:41 am

2 stops18h 26m

$248

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

jue. 11/20

9:00 pm-2:40 pm

2 stops17h 40m

Chicago Midway

lun. 11/24

6:20 am-12:43 am

1 stop18h 23m

$289

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

sáb. 12/6

6:40 am-1:08 pm

1 stop6h 28m

Chicago Midway

sáb. 12/13

6:00 am-12:41 am

2 stops18h 41m

$366

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

jue. 11/13

9:00 pm-6:39 pm

2 stops21h 39m

Chicago Midway

dom. 11/16

6:15 am-3:07 pm

1 stop8h 52m

$380

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

vie. 2/27

7:30 am-11:25 pm

1 stop15h 55m

Chicago Midway

lun. 3/2

8:56 pm-3:30 pm

2 stops18h 34m

$393

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

dom. 11/9

7:30 am-10:03 pm

1 stop14h 33m

Chicago Midway

mié. 11/12

2:06 pm-12:39 am

2 stops34h 33m

$414

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

sáb. 12/6

6:40 am-1:08 pm

1 stop6h 28m

Chicago Midway

sáb. 12/13

7:02 pm-11:45 am

1 stop16h 43m

$431

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

mar. 12/2

5:45 pm-1:08 pm

1 stop19h 23m

Chicago Midway

jue. 12/11

10:36 am-3:07 pm

1 stop28h 31m

$451

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

sáb. 12/6

9:00 pm-6:12 pm

2 stops21h 12m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Showing 1-10 of 17 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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 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 FlightHub the most. FlightHub 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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