$248 Cheap Flights from Chicago (MDW) to Winnipeg (YWG)

View $248 flight on Fri, Feb 6, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)

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Cheap Flights from Chicago to Winnipeg (MDW-YWG)

Prices were available within the past 7 days and start at $248 for one-way flights and $540 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Feb 6 - Sun, Feb 8
MDW
Chicago
YWG
Winnipeg
$540 Roundtrip, found 9 hours ago
$540
Roundtrip
found 9 hours ago
Select Delta flight, departing Fri, Feb 6 from Chicago to Winnipeg, returning Sun, Feb 8, priced at $540 found 9 hours ago
WestJet
Sat, Jun 27 - Thu, Jul 2
MDW
Chicago
YWG
Winnipeg
$574 Roundtrip, found 17 hours ago
$574
Roundtrip
found 17 hours ago
Select WestJet flight, departing Sat, Jun 27 from Chicago to Winnipeg, returning Thu, Jul 2, priced at $574 found 17 hours ago
WestJet
Sat, Jun 27 - Sat, Jul 4
MDW
Chicago
YWG
Winnipeg
$581 Roundtrip, found 4 days ago
$581
Roundtrip
found 4 days ago
Select WestJet flight, departing Sat, Jun 27 from Chicago to Winnipeg, returning Sat, Jul 4, priced at $581 found 4 days ago
WestJet
Sun, Feb 8 - Thu, Feb 12
MDW
Chicago
YWG
Winnipeg
$582 Roundtrip, found 7 hours ago
$582
Roundtrip
found 7 hours ago
Select WestJet flight, departing Sun, Feb 8 from Chicago to Winnipeg, returning Thu, Feb 12, priced at $582 found 7 hours ago
Delta
Fri, Feb 6 - Sun, Feb 8
MDW
Chicago
YWG
Winnipeg
$586 Roundtrip, found 9 hours ago
$586
Roundtrip
found 9 hours ago
Select Delta flight, departing Fri, Feb 6 from Chicago to Winnipeg, returning Sun, Feb 8, priced at $586 found 9 hours ago
WestJet
Tue, Mar 3 - Wed, Mar 4
MDW
Chicago
YWG
Winnipeg
$589 Roundtrip, found 1 day ago
$589
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, Mar 3 from Chicago to Winnipeg, returning Wed, Mar 4, priced at $589 found 1 day ago
WestJet
Fri, Feb 6 - Tue, Feb 10
MDW
Chicago
YWG
Winnipeg
$594 Roundtrip, found 7 hours ago
$594
Roundtrip
found 7 hours ago
Select WestJet flight, departing Fri, Feb 6 from Chicago to Winnipeg, returning Tue, Feb 10, priced at $594 found 7 hours ago
WestJet
Tue, Mar 3 - Wed, Mar 4
MDW
Chicago
YWG
Winnipeg
$596 Roundtrip, found 1 day ago
$596
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, Mar 3 from Chicago to Winnipeg, returning Wed, Mar 4, priced at $596 found 1 day ago
WestJet
Thu, Jan 29 - Thu, Feb 5
MDW
Chicago
YWG
Winnipeg
$602 Roundtrip, found 6 days ago
$602
Roundtrip
found 6 days ago
Select WestJet flight, departing Thu, Jan 29 from Chicago to Winnipeg, returning Thu, Feb 5, priced at $602 found 6 days ago
WestJet
Sun, Feb 8 - Thu, Feb 12
MDW
Chicago
YWG
Winnipeg
$605 Roundtrip, found 7 hours ago
$605
Roundtrip
found 7 hours ago
Select WestJet flight, departing Sun, Feb 8 from Chicago to Winnipeg, returning Thu, Feb 12, priced at $605 found 7 hours ago

Alternative airports near Winnipeg

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Winnipeg Intl. YWG. Cheapest and Closest option available. Average driving time to city center is 15 minutes. Flights from $1,010
YWG
Winnipeg Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $1,010

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) cost?
Grab a cheap one-way flight from $248 or cheap return flight from $540 from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
The cheapest month to fly from MDW to YWG is February, when there's less demand. Off-peak season is often when you'll find lower airfares between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
You can't catch a nonstop flight from Chicago, IL (MDW-Midway Intl.) to Winnipeg James Armstrong Richardson Intl. Airport (YWG). However, you can easily travel to Winnipeg without any layovers by taking off from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest MDW to YWG flight.
How many flights per day from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
You'll have to book a flight with a layover when traveling from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from MDW to YWG?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) route, fly before 3 PM. Flights after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) last-minute?
Booking your plane ticket from MDW to YWG shortly before your trip is generally more expensive. However, if you're flexible with your schedule, you could snag a cheap last-minute fare.
Is it cheaper to book a MDW to YWG flight and hotel package?
Booking a MDW to YWG flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Pick from our extensive range of accommodations and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Typically, you can cancel or reschedule your MDW to YWG flight. However, additional fees may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you want more details, go to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$539
Distance
721 mi

Book with confidence

Chicago to Winnipeg Flights

The cheapest times to fly from Chicago to Winnipeg

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Winnipeg are during the month of February. You can find some of the cheapest flights from Chicago to Winnipeg with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Winnipeg

Sunday is one of the best days to book for cheap flights from Chicago to Winnipeg: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Winnipeg

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Winnipeg in 2026. You can also book with separate airlines for your outbound and return journeys, from $248 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Winnipeg flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Winnipeg airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Winnipeg Flights

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*Available to One Key members.