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

View AU$348 flight on Thu, 4 Dec 2025Opens in a new window

Popular airlines from Chicago O'Hare International 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 35% 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 (ORD) to Winnipeg (YWG)

Prices were available within the past 7 days for one-way flights and round trip tickets 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 AU$368 - AU$1,799 per traveller.

Frequently asked questions

How much is a flight from ORD to Winnipeg Airport?
If you're planning on travelling from O'Hare Intl. Airport (ORD) to Winnipeg Airport, round-trip journeys start from . This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Every air carrier has its own terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from O'Hare Airport to Winnipeg Airport 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 ORD to YWG flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Intl. Airport (ORD) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
The distance from O'Hare Intl. Airport (ORD) (ORD) to YWG (YWG) is just 1 150 kilometres. You'll be stepping off the plane and grabbing your baggage from the carousel before you know it.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Winnipeg Airport?
Unfortunately, there aren't any airlines that directly fly between O'Hare Intl. Airport (ORD) and Winnipeg James Armstrong Richardson Intl. Airport (YWG). You'll need to book a flight with one or more stops.
Are ORD to YWG flight tickets cheaper when they're purchased at the last minute?
Booking last minute from O'Hare Intl. Airport (ORD) to Winnipeg Airport can be hit-or-miss. You may be able to score a bargain, but then again, you could miss out! If you'd prefer to start planning early, Expedia compares flight deals up to a year in advance. Just bear in mind that not all airlines list their prices that far in advance. Our suggestion? Check back often as updates are made regularly.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Distance
1130 km
Average flight time
2 hours 34 mins

Book with confidence

Your quick guide to flights from Chicago to Winnipeg

Pick up great flights from Chicago to Winnipeg

With Expedia, you have your pick of flights a day with 19 airlines covering flights from Chicago to Winnipeg. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Chicago to Winnipeg that take around hours.

Find cheap flights from Chicago to Winnipeg

From the great flight deals with prices currently ranging from to , you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Chicago to Winnipeg around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Winnipeg is normally in .

Reasons to book your flight from Chicago to Winnipeg with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Chicago to Winnipeg across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Winnipeg right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Your quick guide to flights from Chicago to Winnipeg

Explore a world of travel with Expedia

*Available to Expedia members.