$246 Cheap Flights from Winnipeg (YWG) to Chicago (MDW)

View $246 flight on Wed, Oct 29, 2025Opens in a new window

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

Cheap Flights from Winnipeg to Chicago (YWG-MDW)

Prices were available within the past 7 days and start at $246 for one-way flights and $438 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Tue, Oct 28 - Mon, Nov 3
YWG
Winnipeg
MDW
Chicago
$438 Roundtrip, found 2 days ago
$438
Roundtrip
found 2 days ago
Select WestJet flight, departing Tue, Oct 28 from Winnipeg to Chicago, returning Mon, Nov 3, priced at $438 found 2 days ago
WestJet
Tue, Nov 18 - Tue, Nov 25
YWG
Winnipeg
MDW
Chicago
$448 Roundtrip, just found
$448
Roundtrip
just found
Select WestJet flight, departing Tue, Nov 18 from Winnipeg to Chicago, returning Tue, Nov 25, priced at $448 just found
WestJet
Tue, Jan 6 - Sat, Jan 17
YWG
Winnipeg
MDW
Chicago
$450 Roundtrip, found 5 days ago
$450
Roundtrip
found 5 days ago
Select WestJet flight, departing Tue, Jan 6 from Winnipeg to Chicago, returning Sat, Jan 17, priced at $450 found 5 days ago
WestJet
Wed, Oct 22 - Wed, Oct 29
YWG
Winnipeg
MDW
Chicago
$455 Roundtrip, found 2 days ago
$455
Roundtrip
found 2 days ago
Select WestJet flight, departing Wed, Oct 22 from Winnipeg to Chicago, returning Wed, Oct 29, priced at $455 found 2 days ago
WestJet
Tue, Nov 18 - Tue, Nov 25
YWG
Winnipeg
MDW
Chicago
$460 Roundtrip, just found
$460
Roundtrip
just found
Select WestJet flight, departing Tue, Nov 18 from Winnipeg to Chicago, returning Tue, Nov 25, priced at $460 just found
WestJet
Thu, Jan 29 - Sun, Feb 1
YWG
Winnipeg
MDW
Chicago
$461 Roundtrip, found 1 day ago
$461
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Jan 29 from Winnipeg to Chicago, returning Sun, Feb 1, priced at $461 found 1 day ago
WestJet
Tue, Nov 18 - Tue, Nov 25
YWG
Winnipeg
MDW
Chicago
$472 Roundtrip, just found
$472
Roundtrip
just found
Select WestJet flight, departing Tue, Nov 18 from Winnipeg to Chicago, returning Tue, Nov 25, priced at $472 just found
WestJet
Fri, Nov 21 - Mon, Nov 24
YWG
Winnipeg
MDW
Chicago
$473 Roundtrip, found 6 days ago
$473
Roundtrip
found 6 days ago
Select WestJet flight, departing Fri, Nov 21 from Winnipeg to Chicago, returning Mon, Nov 24, priced at $473 found 6 days ago
WestJet
Wed, Oct 22 - Wed, Oct 29
YWG
Winnipeg
MDW
Chicago
$475 Roundtrip, found 2 days ago
$475
Roundtrip
found 2 days ago
Select WestJet flight, departing Wed, Oct 22 from Winnipeg to Chicago, returning Wed, Oct 29, priced at $475 found 2 days ago
Delta
Sun, Oct 26 - Wed, Oct 29
YWG
Winnipeg
MDW
Chicago
$501 Roundtrip, found 23 hours ago
$501
Roundtrip
found 23 hours ago
Select Delta flight, departing Sun, Oct 26 from Winnipeg to Chicago, returning Wed, Oct 29, priced at $501 found 23 hours ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $436
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $436

Frequently asked questions

How much does a flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $246 or cheap return flight from $438 from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW)?
The cheapest month to fly from YWG to MDW is October, when demand is low. Off-peak months are typically when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from YWG to MDW. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW)?
Direct flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from YWG to MDW?
Typically you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW)?
Book a flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**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.
What airports do you fly into for Chicago from Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
If you've booked a direct flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from YWG to MDW right before your trip is usually more expensive. But if there's some wiggle room with your schedule, you could grab a cheap last-minute fare.
Is it cheaper to book a YWG to MDW flight and hotel package?
You'll typically save money by booking a YWG to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've chosen your ideal accommodations and flights, you can add extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Midway Intl. Airport (MDW)?
In most cases, you're able to reschedule or cancel your YWG to MDW flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you want further details, visit our Customer Service portal.

Travel information

Travel information

Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, WestJet
Roundtrip price
$438
Distance
721 mi

Book with confidence

Book with confidence

Winnipeg to Chicago Flights

The cheapest times to fly from Winnipeg to Chicago

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 Winnipeg to Chicago are during the month of October. You can find some of the cheapest flights from Winnipeg to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Winnipeg to Chicago

Sunday is one of the best days to book for cheap flights from Winnipeg to Chicago: 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 Winnipeg to Chicago

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 Winnipeg to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $246 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 Winnipeg to Chicago 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 Winnipeg to Chicago 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.

 

Winnipeg to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.