￥28,900 Cheap Flights from Winnipeg (YWG) to Chicago (CHI)

View ￥28,900 flight on Sun, Dec 7, 2025Opens 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 ￥28,900 for one-way flights and ￥59,320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥59,320 Roundtrip, found 5 hours ago
￥59,320
Roundtrip
found 5 hours ago
Select WestJet flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥59,320 found 5 hours ago
WestJet
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥60,170 Roundtrip, found 5 hours ago
￥60,170
Roundtrip
found 5 hours ago
Select WestJet flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥60,170 found 5 hours ago
WestJet
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥63,120 Roundtrip, found 5 hours ago
￥63,120
Roundtrip
found 5 hours ago
Select WestJet flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥63,120 found 5 hours ago
WestJet
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥64,060 Roundtrip, found 5 hours ago
￥64,060
Roundtrip
found 5 hours ago
Select WestJet flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥64,060 found 5 hours ago
Delta
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥65,020 Roundtrip, found 5 hours ago
￥65,020
Roundtrip
found 5 hours ago
Select Delta flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥65,020 found 5 hours ago
WestJet
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥67,289 Roundtrip, found 5 hours ago
￥67,289
Roundtrip
found 5 hours ago
Select WestJet flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥67,289 found 5 hours ago
WestJet
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥67,330 Roundtrip, found 5 hours ago
￥67,330
Roundtrip
found 5 hours ago
Select WestJet flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥67,330 found 5 hours ago
WestJet
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥68,260 Roundtrip, found 5 hours ago
￥68,260
Roundtrip
found 5 hours ago
Select WestJet flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥68,260 found 5 hours ago
United
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥71,300 Roundtrip, found 5 hours ago
￥71,300
Roundtrip
found 5 hours ago
Select United flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥71,300 found 5 hours ago
Air Canada
Sun, Dec 7 - Sun, Dec 14
YWG
Winnipeg
ORD
Chicago
￥72,290 Roundtrip, found 5 hours ago
￥72,290
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Sun, Dec 7 from Winnipeg to Chicago, returning Sun, Dec 14, priced at ￥72,290 found 5 hours ago

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

October is typically the cheapest month to fly

From ￥36,745 - ￥128,009 per traveler.

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 ￥59,320. 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 many hours is the flight from Winnipeg Airport to Chicago, IL (CHI-All Airports)?
The average flight time between Winnipeg Airport and Chicago, IL (CHI-All Airports) is 5 hours and 6 minutes. If you get peckish on longer flights, pack some healthy snacks in your carry-on luggage.
How far is the flight from Winnipeg Airport to Chicago, IL (CHI-All Airports)?
With a flight distance of 1,100 kilometers, 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.
Can I fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) right now?
To see what travel restrictions and quarantine requirements are in place for different citizens flying from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) please visit our COVID 19 travel advisor portal link.

Travel information

Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Roundtrip price
￥59,320
Distance
1130 km

Book with confidence

Winnipeg to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Winnipeg to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with YWG to CHI flights that won’t make your bank account wince. Ready to temporarily leave behind Winnipeg for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to CHI with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Winnipeg to Chicago Flights

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

Winnipeg to O'Hare Intl.
￥59,320

Madison

*Available to Expedia members.