$157 Cheap Flights from Winnipeg (YWG) to Chicago (CHI)

View $157 flight on Fri, Jan 23, 2026Opens in a new window

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

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Cheap Flights from Winnipeg to Chicago (YWG-CHI)

Prices were available within the past 7 days and start at $157 for one-way flights and $267 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Fri, Jan 23 - Fri, Jan 30
YWG
Winnipeg
ORD
Chicago
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select WestJet flight, departing Fri, Jan 23 from Winnipeg to Chicago, returning Fri, Jan 30, priced at $267 found 6 days ago
WestJet
Fri, Jan 23 - Fri, Jan 30
YWG
Winnipeg
ORD
Chicago
$293 Roundtrip, found 6 days ago
$293
Roundtrip
found 6 days ago
Select WestJet flight, departing Fri, Jan 23 from Winnipeg to Chicago, returning Fri, Jan 30, priced at $293 found 6 days ago
WestJet
Fri, Dec 12 - Mon, Dec 15
YWG
Winnipeg
ORD
Chicago
$293 Roundtrip, found 3 hours ago
$293
Roundtrip
found 3 hours ago
Select WestJet flight, departing Fri, Dec 12 from Winnipeg to Chicago, returning Mon, Dec 15, priced at $293 found 3 hours ago
WestJet
Thu, Mar 19 - Fri, Apr 3
YWG
Winnipeg
ORD
Chicago
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu, Mar 19 from Winnipeg to Chicago, returning Fri, Apr 3, priced at $319 found 4 days ago
WestJet
Fri, Feb 27 - Mon, Mar 16
YWG
Winnipeg
ORD
Chicago
$333 Roundtrip, found 6 days ago
$333
Roundtrip
found 6 days ago
Select WestJet flight, departing Fri, Feb 27 from Winnipeg to Chicago, returning Mon, Mar 16, priced at $333 found 6 days ago
WestJet
Fri, Dec 12 - Mon, Dec 15
YWG
Winnipeg
ORD
Chicago
$334 Roundtrip, found 3 hours ago
$334
Roundtrip
found 3 hours ago
Select WestJet flight, departing Fri, Dec 12 from Winnipeg to Chicago, returning Mon, Dec 15, priced at $334 found 3 hours ago
United
Fri, Dec 12 - Mon, Dec 15
YWG
Winnipeg
ORD
Chicago
$403 Roundtrip, found 3 hours ago
$403
Roundtrip
found 3 hours ago
Select United flight, departing Fri, Dec 12 from Winnipeg to Chicago, returning Mon, Dec 15, priced at $403 found 3 hours ago
Air Canada
Thu, Apr 16 - Mon, Apr 20
YWG
Winnipeg
ORD
Chicago
$412 Roundtrip, found 1 day ago
$412
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Apr 16 from Winnipeg to Chicago, returning Mon, Apr 20, priced at $412 found 1 day ago
Delta
Wed, Dec 3 - Tue, Dec 9
YWG
Winnipeg
ORD
Chicago
$445 Roundtrip, found 1 day ago
$445
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 3 from Winnipeg to Chicago, returning Tue, Dec 9, priced at $445 found 1 day ago
Porter Airlines
Mon, Nov 3 - Tue, Nov 4
YWG
Winnipeg
ORD
Chicago
$888 Roundtrip, found 4 hours ago
$888
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Mon, Nov 3 from Winnipeg to Chicago, returning Tue, Nov 4, priced at $888 found 4 hours ago

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

October is typically the cheapest month to fly

From $248 - $865 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 $695
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $695
Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $695
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $695

Frequently asked questions

How much is a flight from YWG to Chicago, IL (CHI-All Airports)?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) was $267. Fares this good don't wait forever, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from YWG to Chicago, IL (CHI-All Airports)?
We get that life can throw the odd curveball, so we've made it as simple as possible for you to cancel your trip online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from Winnipeg Airport to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for YWG to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Winnipeg Airport to Chicago, IL (CHI-All Airports)?
With a flight distance of 684 mi, it's just a short hop from YWG to Chicago, IL (CHI-All Airports). It might be a quick flight, but it's still worth packing a book to read.
Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports)?
You won't find any airlines flying directly between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Chicago, IL (CHI-All Airports), so be prepared to make at least one stop on your journey. A layover can be a good way to break up a trip!
Are Winnipeg Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) can be hit-or-miss. You may be able to find a bargain, but you could also completely miss out! If you'd prefer to start your trip planning ahead of time, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines publish their prices that far in advance. Our suggestion? Check back often as updates are made frequently.

Travel information

Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Roundtrip price
$266
Distance
706 mi

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 January. 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 $157 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

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*Available to One Key members.