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$160+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MDW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/25. 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 4/138:20 pm
YWG
-
MDW
1 stop13h 45m
Multiple Airlines
Wed 4/154:15 pm
MDW
-
YWG
1 stop16h 25m
Multiple Airlines
Deal found 1/25$313
This FlightHub deal was found by Cheapflights users on 1/26. 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.
Tue 3/35:00 am
YWG
-
MDW
2 stops7h 46m
WestJet
Sun 3/89:35 am
MDW
-
YWG
2 stops9h 49m
WestJet
Deal found 1/26$446
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/205:00 am
YWG
-
MDW
2 stops12h 37m
WestJet
Mon 2/237:20 pm
MDW
-
YWG
1 stop15h 41m
WestJet
Deal found 1/26$448
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 2/268:20 pm
YWG
-
MDW
1 stop13h 50m
Multiple Airlines
Sun 3/19:04 pm
MDW
-
YWG
2 stops27h 37m
Multiple Airlines
Deal found 1/26$453
This FlightHub deal was found by Cheapflights users on 1/24. 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.
Sat 4/2512:53 pm
YWG
-
MDW
1 stop5h 52m
WestJet
Thu 4/301:10 pm
MDW
-
YWG
2 stops9h 50m
WestJet
Deal found 1/24$454
This WestJet deal was found by Cheapflights users on 1/23. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:45 am
YWG
-
MDW
2 stops11h 55m
WestJet
Wed 3/41:49 pm
MDW
-
YWG
1 stop21h 12m
WestJet
Deal found 1/23$468

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$313
(Kiwi.com)

One-way from

$160
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$477
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 ($45 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 January 2026
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 January 26, 2026.
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

Mon 4/13

8:20 pm-10:05 am

1 stop13h 45m

Chicago Midway

Wed 4/15

4:15 pm-8:40 am

1 stop16h 25m

$313

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 4/13

5:00 am-5:58 pm

2 stops12h 58m

Chicago Midway

Wed 4/15

9:27 am-7:09 pm

2 stops9h 42m

$446

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

5:00 am-12:46 pm

2 stops7h 46m

Chicago Midway

Sun 3/8

9:35 am-7:24 pm

2 stops9h 49m

$446

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 2/20

5:00 am-5:37 pm

2 stops12h 37m

Chicago Midway

Mon 2/23

7:20 pm-11:01 am

1 stop15h 41m

$448

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 4/9

5:00 am-5:54 pm

2 stops12h 54m

Chicago Midway

Thu 4/16

9:27 am-7:09 pm

2 stops9h 42m

$452

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 4/25

11:55 am-6:36 pm

1 stop6h 41m

Chicago Midway

Thu 4/30

1:23 pm-12:55 am

2 stops11h 32m

$456

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 3/2

11:53 am-6:40 pm

1 stop6h 47m

Chicago Midway

Wed 3/4

7:20 pm-11:01 am

1 stop15h 41m

$468

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 3/11

7:30 am-10:19 pm

1 stop14h 49m

$160

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 2/24

8:05 pm-10:10 am

1 stop14h 05m

$167

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 4/26

9:05 pm-10:19 pm

2 stops25h 14m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 14 results
1
2
  • 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.

  • 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 58m. 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
Merrillville
Hammond
Porter
Benton Harbor

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