￥29,440 Cheap Flights from Winnipeg (YWG) to Chicago (CHI)

View ￥29,440 flight on Fri, Sep 26, 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 ￥29,440 for one-way flights and ￥55,319 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, Aug 13 - Mon, Aug 18
YWG
Winnipeg
ORD
Chicago
￥55,319 Roundtrip, found 6 days ago
￥55,319
Roundtrip
found 6 days ago
Select United flight, departing Wed, Aug 13 from Winnipeg to Chicago, returning Mon, Aug 18, priced at ￥55,319 found 6 days ago
Air Canada
Wed, Aug 13 - Mon, Aug 18
YWG
Winnipeg
ORD
Chicago
￥56,299 Roundtrip, found 6 days ago
￥56,299
Roundtrip
found 6 days ago
Select Air Canada flight, departing Wed, Aug 13 from Winnipeg to Chicago, returning Mon, Aug 18, priced at ￥56,299 found 6 days ago

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

September is typically the cheapest month to fly

From ￥42,306 - ￥82,103 per traveler.

Graph displaying average flight prices per month

Flights from Winnipeg (YWG) to Chicago (ORD)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Roundtrip price
￥55,319
Distance
1130 km

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.

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 ￥55,319. 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.

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