$207 Cheap Flights from Winnipeg (YWG) to Chicago (MDW)

View $207 flight on Thu, Sep 4, 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 $207 for one-way flights and $355 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 25 - Tue, Nov 4
YWG
Winnipeg
MDW
Chicago
$355 Roundtrip, found 6 days ago
$355
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 25 from Winnipeg to Chicago, returning Tue, Nov 4, priced at $355 found 6 days ago
Delta
Tue, Sep 23 - Sat, Oct 11
YWG
Winnipeg
MDW
Chicago
$361 Roundtrip, found 6 days ago
$361
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 23 from Winnipeg to Chicago, returning Sat, Oct 11, priced at $361 found 6 days ago
Delta
Tue, Aug 26 - Sat, Sep 6
YWG
Winnipeg
MDW
Chicago
$376 Roundtrip, found 6 days ago
$376
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 26 from Winnipeg to Chicago, returning Sat, Sep 6, priced at $376 found 6 days ago
Delta
Sat, Oct 25 - Wed, Oct 29
YWG
Winnipeg
MDW
Chicago
$377 Roundtrip, found 8 hours ago
$377
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Oct 25 from Winnipeg to Chicago, returning Wed, Oct 29, priced at $377 found 8 hours ago
Delta
Mon, Sep 29 - Sat, Oct 11
YWG
Winnipeg
MDW
Chicago
$384 Roundtrip, found 6 days ago
$384
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Sep 29 from Winnipeg to Chicago, returning Sat, Oct 11, priced at $384 found 6 days ago
Delta
Fri, Oct 24 - Tue, Nov 4
YWG
Winnipeg
MDW
Chicago
$391 Roundtrip, found 6 days ago
$391
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Oct 24 from Winnipeg to Chicago, returning Tue, Nov 4, priced at $391 found 6 days ago
Delta
Sat, Sep 20 - Mon, Sep 22
YWG
Winnipeg
MDW
Chicago
$393 Roundtrip, found 1 day ago
$393
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 20 from Winnipeg to Chicago, returning Mon, Sep 22, priced at $393 found 1 day ago
Delta
Fri, Sep 26 - Wed, Oct 15
YWG
Winnipeg
MDW
Chicago
$395 Roundtrip, found 6 days ago
$395
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 26 from Winnipeg to Chicago, returning Wed, Oct 15, priced at $395 found 6 days ago
Delta
Tue, Sep 2 - Sat, Sep 20
YWG
Winnipeg
MDW
Chicago
$398 Roundtrip, found 6 days ago
$398
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Sep 2 from Winnipeg to Chicago, returning Sat, Sep 20, priced at $398 found 6 days ago
WestJet
Tue, Oct 28 - Tue, Nov 11
YWG
Winnipeg
MDW
Chicago
$443 Roundtrip, found 6 days ago
$443
Roundtrip
found 6 days ago
Select WestJet flight, departing Tue, Oct 28 from Winnipeg to Chicago, returning Tue, Nov 11, priced at $443 found 6 days 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 $332
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $332
Flights from Winnipeg (YWG) to Chicago (MDW)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Midway Intl.
Airlines serving
WestJet
Roundtrip price
$354
Distance
721 mi

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 $207 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.

 

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 $207 or cheap return flight from $355 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.

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*Available to One Key members.