NZ$251 Cheap Flights Chicago to Winnipeg (ORD-YWG)

View NZ$251 flight on Mon, 8 Dec 2025Opens in a new window

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

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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.

WestJet
Mon, 24 Nov - Fri, 12 Dec
ORD
Chicago
YWG
Winnipeg
NZ$587 Return, found 1 day ago
NZ$587
Return
found 1 day ago
Select WestJet flight, departing Mon, 24 Nov from Chicago to Winnipeg, returning Fri, 12 Dec, priced at NZ$587 found 1 day ago
WestJet
Fri, 14 Nov - Fri, 5 Dec
ORD
Chicago
YWG
Winnipeg
NZ$633 Return, found 1 day ago
NZ$633
Return
found 1 day ago
Select WestJet flight, departing Fri, 14 Nov from Chicago to Winnipeg, returning Fri, 5 Dec, priced at NZ$633 found 1 day ago
WestJet
Thu, 23 Oct - Mon, 10 Nov
ORD
Chicago
YWG
Winnipeg
NZ$730 Return, found 1 day ago
NZ$730
Return
found 1 day ago
Select WestJet flight, departing Thu, 23 Oct from Chicago to Winnipeg, returning Mon, 10 Nov, priced at NZ$730 found 1 day ago
WestJet
Thu, 23 Oct - Mon, 3 Nov
ORD
Chicago
YWG
Winnipeg
NZ$731 Return, found 2 days ago
NZ$731
Return
found 2 days ago
Select WestJet flight, departing Thu, 23 Oct from Chicago to Winnipeg, returning Mon, 3 Nov, priced at NZ$731 found 2 days ago
WestJet
Mon, 24 Nov - Mon, 8 Dec
ORD
Chicago
YWG
Winnipeg
NZ$733 Return, found 1 day ago
NZ$733
Return
found 1 day ago
Select WestJet flight, departing Mon, 24 Nov from Chicago to Winnipeg, returning Mon, 8 Dec, priced at NZ$733 found 1 day ago
WestJet
Fri, 14 Nov - Mon, 1 Dec
ORD
Chicago
YWG
Winnipeg
NZ$779 Return, found 1 day ago
NZ$779
Return
found 1 day ago
Select WestJet flight, departing Fri, 14 Nov from Chicago to Winnipeg, returning Mon, 1 Dec, priced at NZ$779 found 1 day ago
WestJet
Sat, 11 Oct - Sat, 18 Oct
ORD
Chicago
YWG
Winnipeg
NZ$798 Return, found 5 days ago
NZ$798
Return
found 5 days ago
Select WestJet flight, departing Sat, 11 Oct from Chicago to Winnipeg, returning Sat, 18 Oct, priced at NZ$798 found 5 days ago
United
Thu, 23 Oct - Thu, 6 Nov
ORD
Chicago
YWG
Winnipeg
NZ$804 Return, found 2 days ago
NZ$804
Return
found 2 days ago
Select United flight, departing Thu, 23 Oct from Chicago to Winnipeg, returning Thu, 6 Nov, priced at NZ$804 found 2 days ago
Delta
Tue, 14 Oct - Tue, 21 Oct
ORD
Chicago
YWG
Winnipeg
NZ$815 Return, found 2 days ago
NZ$815
Return
found 2 days ago
Select Delta flight, departing Tue, 14 Oct from Chicago to Winnipeg, returning Tue, 21 Oct, priced at NZ$815 found 2 days ago
Air Canada
Thu, 23 Oct - Thu, 6 Nov
ORD
Chicago
YWG
Winnipeg
NZ$853 Return, found 2 days ago
NZ$853
Return
found 2 days ago
Select Air Canada flight, departing Thu, 23 Oct from Chicago to Winnipeg, returning Thu, 6 Nov, priced at NZ$853 found 2 days ago

Alternative airports near Winnipeg

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Winnipeg Intl. YWG. Cheapest and Closest option available. Average driving time to city centre is 15 minutes. Flights from NZ$812
YWG
Winnipeg Intl.
CheapestClosest
Average driving time to city centre15 min
Flights from NZ$812
Flight from Chicago to Winnipeg route information
Origin airport
O'Hare Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Return price
NZ$586
Distance
1130 km
Average flight time
2 hours 34 mins

Perfect flights from Chicago to Winnipeg

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Winnipeg. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of Winnipeg, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible O'Hare Intl. to Winnipeg James Armstrong Richardson Intl. ticket options cater to your travel preferences, with incredible one-way fares from NZ$251 and roundtrip prices from NZ$587. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Winnipeg James Armstrong Richardson Intl. and explore Winnipeg and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your ORD to YWG travel arrangements today and embark on the journey of a lifetime in Winnipeg.

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 NZ$587. 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.

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