£122 Cheap Flights from Chicago (ORD) to Winnipeg (YWG)

View £122 flight on Mon, 15 Jun 2026Opens 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 and start at £122 for one-way flights and £288 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Fri, 25 Sept - Fri, 2 Oct
ORD
Chicago
YWG
Winnipeg
£288 Return, found 3 days ago
£288
Return
found 3 days ago
Select WestJet flight, departing Fri, 25 Sept from Chicago to Winnipeg, returning Fri, 2 Oct, priced at £288 found 3 days ago
WestJet
Fri, 25 Sept - Fri, 2 Oct
ORD
Chicago
YWG
Winnipeg
£311 Return, found 3 days ago
£311
Return
found 3 days ago
Select WestJet flight, departing Fri, 25 Sept from Chicago to Winnipeg, returning Fri, 2 Oct, priced at £311 found 3 days ago
WestJet
Thu, 13 Aug - Fri, 14 Aug
ORD
Chicago
YWG
Winnipeg
£323 Return, found 4 days ago
£323
Return
found 4 days ago
Select WestJet flight, departing Thu, 13 Aug from Chicago to Winnipeg, returning Fri, 14 Aug, priced at £323 found 4 days ago
WestJet
Fri, 25 Sept - Fri, 2 Oct
ORD
Chicago
YWG
Winnipeg
£336 Return, found 3 days ago
£336
Return
found 3 days ago
Select WestJet flight, departing Fri, 25 Sept from Chicago to Winnipeg, returning Fri, 2 Oct, priced at £336 found 3 days ago
WestJet
Thu, 13 Aug - Fri, 14 Aug
ORD
Chicago
YWG
Winnipeg
£345 Return, found 4 days ago
£345
Return
found 4 days ago
Select WestJet flight, departing Thu, 13 Aug from Chicago to Winnipeg, returning Fri, 14 Aug, priced at £345 found 4 days ago
WestJet
Fri, 25 Sept - Fri, 2 Oct
ORD
Chicago
YWG
Winnipeg
£359 Return, found 3 days ago
£359
Return
found 3 days ago
Select WestJet flight, departing Fri, 25 Sept from Chicago to Winnipeg, returning Fri, 2 Oct, priced at £359 found 3 days ago
American Airlines
Tue, 20 Oct - Sat, 24 Oct
ORD
Chicago
YWG
Winnipeg
£373 Return, found 6 days ago
£373
Return
found 6 days ago
Select American Airlines flight, departing Tue, 20 Oct from Chicago to Winnipeg, returning Sat, 24 Oct, priced at £373 found 6 days ago
Delta
Tue, 20 Oct - Sat, 24 Oct
ORD
Chicago
YWG
Winnipeg
£414 Return, found 6 days ago
£414
Return
found 6 days ago
Select Delta flight, departing Tue, 20 Oct from Chicago to Winnipeg, returning Sat, 24 Oct, priced at £414 found 6 days ago
Air Canada
Wed, 17 Jun - Wed, 24 Jun
ORD
Chicago
YWG
Winnipeg
£492 Return, found 2 days ago
£492
Return
found 2 days ago
Select Air Canada flight, departing Wed, 17 Jun from Chicago to Winnipeg, returning Wed, 24 Jun, priced at £492 found 2 days ago
United
Tue, 20 Oct - Sat, 24 Oct
ORD
Chicago
YWG
Winnipeg
£526 Return, found 6 days ago
£526
Return
found 6 days ago
Select United flight, departing Tue, 20 Oct from Chicago to Winnipeg, returning Sat, 24 Oct, priced at £526 found 6 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 £612
YWG
Winnipeg Intl.
CheapestClosest
Average driving time to city centre15 min
Flights from £612

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) cost?
One-way flights typically cost between £400 and £1,219 and return flights often range between £863 and £2,188. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
September is typically the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.), with average return fares of approximately £648. This is about 22% lower than the average price throughout the year. September often sees lower prices as the summer travel season winds down and before the holiday rush begins, leading to reduced demand. Other cheap months to fly from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) include August and October.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
Enter ORD to YWG and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
The best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) (ORD) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) (YWG) will differ from traveller to traveller. If you like to fly early, UA offers early morning flights. If price is the most important factor, UA typically offers the lowest fares. DL offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) (ORD) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) (YWG), which is brilliant if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
When looking for the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.), you'll find that September and October offer the cheapest fares, with an average price of around £648 for a return flight. However, the most popular months for this route are December and May, which means you'll have plenty of flight options during those times. While there isn't a single month that is both the cheapest and most popular, if you prioritize savings, aim for September or October. If having a wide selection of flights is more important, consider December or May, keeping in mind that prices might be higher. This information is based on booking data from the past year.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
There are approximately 2 nonstop flights per day from Chicago, IL (ORD-O'Hare Intl.) (ORD) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) (YWG). For even more choice, look at flights that include layovers, as there are around 56 connecting flights per day. Some common connection points include Pearson Intl. (YYZ), Minneapolis - St. Paul Intl. (MSP), and Hartsfield-Jackson Atlanta Intl. (ATL).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
The earliest flight from Chicago O'Hare International Airport (ORD) to Winnipeg James Armstrong Richardson International (YWG) typically departs at approximately 5:00 AM local time. This service is operated by United Airlines and Air Canada. This is a seasonal service active only in July. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
You'll typically find the most flights from Chicago, IL (ORD-O'Hare Intl.) (ORD) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) (YWG) on a Thursday, with around 45 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United Airlines, Delta Air Lines, and Air Canada. Thursdays offer notably more flight options compared to other days of the week.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
The most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) are in the morning, from 9am to 12pm. About 33% of passengers prefer this time. This timing works well because it allows you to start your travel day without being too early, and you'll arrive in Winnipeg with plenty of time to settle in.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
A nonstop flight from ORD to YWG typically takes around 2 hours 50 minutes, covering approximately 707 miles. Connecting flights on this route usually add 3 hours 40 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
Select the "Business class" and "First class" filters when looking for ORD to YWG flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How much is a business class flight from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
A direct, return business class ticket from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) typically costs between £1,285 - £1,441. A non-stop, one-way business class flight is usually around £1,024 - £1,161. You may also be able to find a cheaper business class journey between Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Anaa (AAA) (AAA) to Toronto, ON (YYZ-Pearson Intl.) (YYZ) if you opt for a connecting flight.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Winnipeg from O'Hare Intl. (ORD)?
If you're planning to travel to Winnipeg from O'Hare Intl. (ORD), you can fly directly into Winnipeg James Armstrong Richardson Intl. (YWG) Some flights may connect through major hubs like Minneapolis - St. Paul Intl. (MSP), Detroit Metropolitan Wayne County (DTW), Hartsfield-Jackson Atlanta Intl. (ATL) before reaching Winnipeg. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Air Canada, WestJet
Return price
£287
Distance
1130 km
Average flight time
2 hours 34 mins

Book with confidence

Compare flights from Chicago to Winnipeg easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to Winnipeg. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Winnipeg James Armstrong Richardson Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from O'Hare Intl. (ORD) to Winnipeg James Armstrong Richardson Intl. (YWG)

The easiest way to view the best deals on flights from Chicago to Winnipeg today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl. start at just £288 and range up to £526.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Chicago and Winnipeg
  • booking your flight during September, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Chicago to Winnipeg flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from Chicago to Winnipeg easily and book with confidence

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