$118 Cheap Flights from Winnipeg (YWG) to Chicago (ORD)

View $118 flight on Mon, Jun 9, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Winnipeg to Chicago (YWG-ORD)

Prices were available within the past 7 days and start at $118 for one-way flights and $182 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Tue, Jun 10 - Sun, Jun 22
YWG
Winnipeg
ORD
Chicago
$182 Roundtrip, found 3 days ago
$182
Roundtrip
found 3 days ago
Select WestJet flight, departing Tue, Jun 10 from Winnipeg to Chicago, returning Sun, Jun 22, priced at $182 found 3 days ago
WestJet
Sun, May 18 - Wed, Jun 4
YWG
Winnipeg
ORD
Chicago
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Select WestJet flight, departing Sun, May 18 from Winnipeg to Chicago, returning Wed, Jun 4, priced at $185 found 3 days ago
WestJet
Tue, Jun 10 - Sat, Jun 21
YWG
Winnipeg
ORD
Chicago
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select WestJet flight, departing Tue, Jun 10 from Winnipeg to Chicago, returning Sat, Jun 21, priced at $209 found 3 days ago
WestJet
Mon, Jun 9 - Tue, Jun 17
YWG
Winnipeg
ORD
Chicago
$215 Roundtrip, found 10 hours ago
$215
Roundtrip
found 10 hours ago
Select WestJet flight, departing Mon, Jun 9 from Winnipeg to Chicago, returning Tue, Jun 17, priced at $215 found 10 hours ago
WestJet
Fri, Jun 27 - Sat, Jul 12
YWG
Winnipeg
ORD
Chicago
$218 Roundtrip, found 3 days ago
$218
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Jun 27 from Winnipeg to Chicago, returning Sat, Jul 12, priced at $218 found 3 days ago
WestJet
Mon, Jun 9 - Sun, Jun 22
YWG
Winnipeg
ORD
Chicago
$233 Roundtrip, found 3 days ago
$233
Roundtrip
found 3 days ago
Select WestJet flight, departing Mon, Jun 9 from Winnipeg to Chicago, returning Sun, Jun 22, priced at $233 found 3 days ago
WestJet
Mon, Jun 9 - Tue, Jun 24
YWG
Winnipeg
ORD
Chicago
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Select WestJet flight, departing Mon, Jun 9 from Winnipeg to Chicago, returning Tue, Jun 24, priced at $235 found 3 days ago
Delta
Wed, May 28 - Sat, May 31
YWG
Winnipeg
ORD
Chicago
$335 Roundtrip, found 1 day ago
$335
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 28 from Winnipeg to Chicago, returning Sat, May 31, priced at $335 found 1 day ago
United
Mon, Jun 23 - Mon, Jun 30
YWG
Winnipeg
ORD
Chicago
$404 Roundtrip, found 5 days ago
$404
Roundtrip
found 5 days ago
Select United flight, departing Mon, Jun 23 from Winnipeg to Chicago, returning Mon, Jun 30, priced at $404 found 5 days ago
Air Canada
Tue, Jun 3 - Sun, Jun 8
YWG
Winnipeg
ORD
Chicago
$405 Roundtrip, found 1 day ago
$405
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Jun 3 from Winnipeg to Chicago, returning Sun, Jun 8, priced at $405 found 1 day ago
Flights from Winnipeg (YWG) to Chicago (ORD)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Delta, United, WestJet
Roundtrip price
$182
Distance
706 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 June. 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 $118 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 O'Hare Intl. Airport (ORD) cost?
Cheap return fares from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O’Hare Intl. Airport (ORD) start from $429. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving YWG on May 16 2025 and touching down at ORD. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from YWG to ORD?
The cheapest flights from YWG to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
Catch a direct flight with United Airlines and journey straight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from YWG to ORD?
Take off from YWG to ORD with United. This carrier currently has the lowest one-way fare for this route, starting from $251. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from YWG on May 19 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
On average, only 1 nonstop flight departs daily from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O’Hare Intl. Airport (ORD). Looking for more options? Use Expedia’s filters to find flights with layovers and add a new destination to your journey.
What are the most popular departure times for flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
The 2 PM departures from YWG to ORD are typically the busiest. Greater demand means you’ll likely pay more for these departures. If you want to save money, pick a less crowded time to fly.
What day of the week has the most flights from YWG to ORD?
If you travel on a Sunday, you’ll get the biggest range of choices for flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
Take the earliest flight at around 2:15PM UTC-6, heading out of Winnipeg James Armstrong Richardson Intl. Airport (YWG). You’ll be in the air for roughly 2h 36m, landing at O’Hare Intl. Airport (ORD) at approximately 4:51PM UTC-6.
How long does it take to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
Flights from YWG to ORD have an average travel time of 2 hours and 36 minutes. The distance between these two airports is 710 mi.
What is the best time to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
To touch down at O’Hare Intl. Airport (ORD) without delays, opt for a flight that takes off from Winnipeg James Armstrong Richardson Intl. Airport (YWG) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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)?
Explore your flight options from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O’Hare Intl. Airport (ORD). This is the only Chicago airport you can arrive at if you’re taking a direct flight.
Is it cheaper to buy a plane ticket from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from YWG to ORD shortly before your journey is usually more expensive. However, if there’s some wiggle room with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a YWG to ORD flight and hotel package?
Opting for a YWG to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our impressive range of accommodations and then add activities, flights and car rentals 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
If you reserved your YWG to ORD flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.