₹24,443 Cheap Flights from Winnipeg (YWG) to Chicago (ORD)

View ₹24,443 flight on Thu, 15 Jan 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at ₹24,443 for one-way flights and ₹44,464 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, 15 Jan - Thu, 26 Mar
YWG
Winnipeg
ORD
Chicago
₹44,464 Return, found 22 hours ago
₹44,464
Return
found 22 hours ago
Select United flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Thu, 26 Mar, priced at ₹44,464 found 22 hours ago
Air Canada
Thu, 15 Jan - Thu, 26 Mar
YWG
Winnipeg
ORD
Chicago
₹44,763 Return, found 22 hours ago
₹44,763
Return
found 22 hours ago
Select Air Canada flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Thu, 26 Mar, priced at ₹44,763 found 22 hours ago
Delta
Thu, 15 Jan - Thu, 26 Mar
YWG
Winnipeg
ORD
Chicago
₹44,968 Return, found 22 hours ago
₹44,968
Return
found 22 hours ago
Select Delta flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Thu, 26 Mar, priced at ₹44,968 found 22 hours ago
Air Canada
Thu, 15 Jan - Thu, 26 Mar
YWG
Winnipeg
ORD
Chicago
₹45,052 Return, found 22 hours ago
₹45,052
Return
found 22 hours ago
Select Air Canada flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Thu, 26 Mar, priced at ₹45,052 found 22 hours ago
Air Canada
Thu, 15 Jan - Tue, 31 Mar
YWG
Winnipeg
ORD
Chicago
₹45,062 Return, found 23 hours ago
₹45,062
Return
found 23 hours ago
Select Air Canada flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Tue, 31 Mar, priced at ₹45,062 found 23 hours ago
Air Canada
Thu, 15 Jan - Mon, 19 Jan
YWG
Winnipeg
ORD
Chicago
₹45,351 Return, found 22 hours ago
₹45,351
Return
found 22 hours ago
Select Air Canada flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Mon, 19 Jan, priced at ₹45,351 found 22 hours ago
Air Canada
Thu, 15 Jan - Mon, 19 Jan
YWG
Winnipeg
ORD
Chicago
₹45,640 Return, found 22 hours ago
₹45,640
Return
found 22 hours ago
Select Air Canada flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Mon, 19 Jan, priced at ₹45,640 found 22 hours ago
United
Thu, 15 Jan - Tue, 31 Mar
YWG
Winnipeg
ORD
Chicago
₹47,100 Return, found 23 hours ago
₹47,100
Return
found 23 hours ago
Select United flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Tue, 31 Mar, priced at ₹47,100 found 23 hours ago
United
Thu, 15 Jan - Fri, 27 Mar
YWG
Winnipeg
ORD
Chicago
₹47,180 Return, found 22 hours ago
₹47,180
Return
found 22 hours ago
Select United flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Fri, 27 Mar, priced at ₹47,180 found 22 hours ago
Air Canada
Thu, 15 Jan - Tue, 31 Mar
YWG
Winnipeg
ORD
Chicago
₹47,399 Return, found 23 hours ago
₹47,399
Return
found 23 hours ago
Select Air Canada flight, departing Thu, 15 Jan from Winnipeg to Chicago, returning Tue, 31 Mar, priced at ₹47,399 found 23 hours ago

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

October is typically the cheapest month to fly

From ₹19,121 - ₹43,840 per traveller.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from ₹70,966
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from ₹70,966
Flight from Winnipeg to Chicago route information
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, Delta, United
Return price
₹44,464
Distance
1130 km
Average flight time
2 hours 41 mins

Perfect flights from Winnipeg to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Winnipeg to Chicago. 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 , 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 Winnipeg James Armstrong Richardson Intl. to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from ₹24,443 and roundtrip prices from ₹44,464. 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 O'Hare Intl. and explore 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 to travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from Winnipeg Airport to ORD?
Round-trip flights from Winnipeg Airport to ORD start from ₹44,464. This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — book today so you don't miss out. 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 O'Hare Airport?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from YWG to O'Hare Intl. Airport (ORD) 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Winnipeg Airport to O'Hare Airport?
With a flight distance of 1,150 kilometres, it's just a hop from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport. It might be a quick journey, but it's still worth bringing a book to read.
Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport?
If you want to fly straight from Winnipeg Airport to O'Hare Airport, you'll need to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Flight prices are constantly going up and down, so not always. While last-minute deals between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and ORD are of course possible, it's also a good idea to keep a close eye on prices well before you fly. In fact, some carriers release their prices up to a year ahead of the departure date. Expedia is constantly updating the biggest airfare bargains around, so keep checking and be ready to pounce when the price is low.

Explore a world of travel with Expedia

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