￥33,080 Cheap Flights from Chicago (ORD) to Winnipeg (YWG)

View ￥33,080 flight on Wed, Dec 3, 2025Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Winnipeg (ORD-YWG)

Prices were available within the past 7 days and start at ￥33,080 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

October is typically the cheapest month to fly

From ￥35,234 - ￥101,480 per traveler.
Flights from Chicago (ORD) to Winnipeg (YWG)
Origin airport
O'Hare Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Distance
1130 km
Average flight time
2 hours 35 mins

Chicago to Winnipeg 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 Chicago 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 Winnipeg.

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 ORD to YWG flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago 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 YWG 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 O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Start packing your bags, because round-trip flights from O'Hare Intl. Airport (ORD) to Winnipeg Airport start from . That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book today to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
We understand that life can throw the odd curveball, so we've made it as simple as possible for you to cancel your flight online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) 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 O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from O'Hare Intl. Airport (ORD) to YWG?
The flight time from ORD to Winnipeg James Armstrong Richardson Intl. Airport (YWG) is approximately 4 hours and 58 minutes. Grab your headphones, listen to your favorite tunes and your trip will fly by.
How far is the flight from ORD to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
With a flight distance of 1,150 kilometers, it's only a hop from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG). It might be a quick journey, but it's still worth bringing along something to keep you entertained on board.
Which airlines fly direct from O'Hare Airport to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
You won't find any airlines operating directly between O'Hare Intl. Airport (ORD) and YWG, so be prepared to make at least one stop on your journey. A layover, whether short or long, can be a welcome way to break up a trip!
Are O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) flight tickets cheaper when they're purchased at the last minute?
It is possible to find a great last-minute deal from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG), but there's no guarantee. As many airlines release seats up to 12 months in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a bargain. Expedia compares air carrier prices and updates flight deals often, so you can be sure you're always seeing the latest offers.

Explore a world of travel with Expedia

*Available to Expedia members.