$159 Cheap Flights from Winnipeg (YWG) to Chicago (ORD)

View $159 flight on Mon, Feb 2, 2026Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Winnipeg to Chicago (YWG-ORD)

Prices were available within the past 7 days and start at $159 for one-way flights and $268 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Mon, Feb 9 - Fri, Feb 27
YWG
Winnipeg
ORD
Chicago
$268 Roundtrip, found 4 hours ago
$268
Roundtrip
found 4 hours ago
Select WestJet flight, departing Mon, Feb 9 from Winnipeg to Chicago, returning Fri, Feb 27, priced at $268 found 4 hours ago
WestJet
Thu, Feb 12 - Fri, Feb 27
YWG
Winnipeg
ORD
Chicago
$294 Roundtrip, found 4 hours ago
$294
Roundtrip
found 4 hours ago
Select WestJet flight, departing Thu, Feb 12 from Winnipeg to Chicago, returning Fri, Feb 27, priced at $294 found 4 hours ago
WestJet
Mon, Jan 5 - Fri, Jan 9
YWG
Winnipeg
ORD
Chicago
$318 Roundtrip, found 3 days ago
$318
Roundtrip
found 3 days ago
Select WestJet flight, departing Mon, Jan 5 from Winnipeg to Chicago, returning Fri, Jan 9, priced at $318 found 3 days ago
WestJet
Mon, Feb 9 - Mon, Feb 23
YWG
Winnipeg
ORD
Chicago
$336 Roundtrip, found 4 hours ago
$336
Roundtrip
found 4 hours ago
Select WestJet flight, departing Mon, Feb 9 from Winnipeg to Chicago, returning Mon, Feb 23, priced at $336 found 4 hours ago
Porter Airlines
Fri, Feb 27 - Fri, Mar 13
YWG
Winnipeg
ORD
Chicago
$338 Roundtrip, found 20 hours ago
$338
Roundtrip
found 20 hours ago
Select Porter Airlines flight, departing Fri, Feb 27 from Winnipeg to Chicago, returning Fri, Mar 13, priced at $338 found 20 hours ago
Porter Airlines
Mon, Feb 9 - Mon, Feb 16
YWG
Winnipeg
ORD
Chicago
$340 Roundtrip, found 11 hours ago
$340
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Mon, Feb 9 from Winnipeg to Chicago, returning Mon, Feb 16, priced at $340 found 11 hours ago
Porter Airlines
Fri, Jan 16 - Mon, Jan 19
YWG
Winnipeg
ORD
Chicago
$342 Roundtrip, found 19 hours ago
$342
Roundtrip
found 19 hours ago
Select Porter Airlines flight, departing Fri, Jan 16 from Winnipeg to Chicago, returning Mon, Jan 19, priced at $342 found 19 hours ago
Delta
Mon, Feb 9 - Mon, Feb 16
YWG
Winnipeg
ORD
Chicago
$379 Roundtrip, found 11 hours ago
$379
Roundtrip
found 11 hours ago
Select Delta flight, departing Mon, Feb 9 from Winnipeg to Chicago, returning Mon, Feb 16, priced at $379 found 11 hours ago
United
Fri, Dec 12 - Mon, Dec 15
YWG
Winnipeg
ORD
Chicago
$405 Roundtrip, found 5 days ago
$405
Roundtrip
found 5 days ago
Select United flight, departing Fri, Dec 12 from Winnipeg to Chicago, returning Mon, Dec 15, priced at $405 found 5 days ago
Air Canada
Fri, Dec 12 - Mon, Dec 15
YWG
Winnipeg
ORD
Chicago
$410 Roundtrip, found 5 days ago
$410
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Dec 12 from Winnipeg to Chicago, returning Mon, Dec 15, priced at $410 found 5 days ago

Find the cheapest month to fly from Winnipeg (YWG) to Chicago (ORD)

October is typically the cheapest month to fly

From $215 - $876 per traveler.

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 $560
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $560
Flights from Winnipeg (YWG) to Chicago (ORD)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Delta, Porter Airlines, United, WestJet
Roundtrip price
$268
Distance
706 mi
Average flight time
2 hours 41 mins

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 February. 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 $159 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?
Get a cheap one-way flight from $159 or cheap return flight from $268 from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD) 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from YWG to ORD is February, when there's less demand. Off-peak season is typically when you'll find cheap fares for travel between these airports.
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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest YWG to ORD flight.
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.