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

View AU$318 flight on Mon, 24 Aug 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 for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$653 Return, found 6 days ago
AU$653
Return
found 6 days ago
Select Delta flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$653 found 6 days ago
Delta
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$693 Return, found 6 days ago
AU$693
Return
found 6 days ago
Select Delta flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$693 found 6 days ago
Delta
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$696 Return, found 6 days ago
AU$696
Return
found 6 days ago
Select Delta flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$696 found 6 days ago
WestJet
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$706 Return, found 6 days ago
AU$706
Return
found 6 days ago
Select WestJet flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$706 found 6 days ago
Delta
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$735 Return, found 6 days ago
AU$735
Return
found 6 days ago
Select Delta flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$735 found 6 days ago
WestJet
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$749 Return, found 6 days ago
AU$749
Return
found 6 days ago
Select WestJet flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$749 found 6 days ago
Delta
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$762 Return, found 6 days ago
AU$762
Return
found 6 days ago
Select Delta flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$762 found 6 days ago
Delta
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$766 Return, found 6 days ago
AU$766
Return
found 6 days ago
Select Delta flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$766 found 6 days ago
Delta
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$786 Return, found 6 days ago
AU$786
Return
found 6 days ago
Select Delta flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$786 found 6 days ago
United
Mon, 24 Aug - Mon, 31 Aug
ORD
Chicago
YWG
Winnipeg
AU$1,083 Return, found 6 days ago
AU$1,083
Return
found 6 days ago
Select United flight, departing Mon, 24 Aug from Chicago to Winnipeg, returning Mon, 31 Aug, priced at AU$1,083 found 6 days ago

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

April is typically the cheapest month to fly

From AU$372 - AU$867 per traveller.

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?
You can find one-way and return flights from ORD to YWG with Expedia. 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 our cheapest fares first, and use the Price Tracking tool to receive alerts when ORD to YWG ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD) to Winnipeg, MB (YWG)?
The cheapest months to fly from Chicago, IL (ORD) to Winnipeg, MB (YWG) are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
There are 2 airlines offering direct flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.). Here are the carriers:
  • United operates 15 direct flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) every week.
  • Air Canada operates 14 direct flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) every week.
How do I find cheap flights from Chicago, IL (ORD) to Winnipeg, MB (YWG)?
To find a cheap flight from Chicago, IL (ORD) to Winnipeg, MB (YWG), 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.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. Delta offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.), which is great 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.)?
The best time to fly from Chicago O'Hare International Airport (ORD) to Winnipeg James Armstrong Richardson International Airport (YWG) is typically September or October. These months offer a great balance, with return flights averaging around AU$696. This information is Suggesting these months provide good value for your trip.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
You'll find approximately 2 nonstop flights per day from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.). For even more choices, look at flights that include layovers, as there are around 61 connecting flights per day. Some common connection points include Pearson Intl. (YYZ), Minneapolis - St. Paul Intl. (MSP), and Detroit Metropolitan Wayne County (DTW).
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 Airport (YWG) typically departs around 5:00 AM. This service is offered by American Airlines and Porter Airlines, but it's a seasonal service active only in May. An early departure like this can help you make the most of 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 O'Hare International Airport (ORD) to Winnipeg James Armstrong Richardson International Airport (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, Delta, and Air Canada. Thursday offers notably more flight options compared to other days of the week, making it a good day to consider if you're looking for more choices.
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 O'Hare International Airport (ORD) to Winnipeg James Armstrong Richardson International Airport (YWG) are in the morning, between 9am and 12pm. Many major carriers, including United, Air Canada and Delta, offer flights during this window. Many travellers prefer these times as they allow for an early start to your journey, getting you to your destination with plenty of time left in the day.
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 Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.) typically takes around 2 hours 48 minutes. This route covers a distance of approximately 1,138 kilometres (707 miles). If you opt for a one-stop flight, your travel time will be longer, usually around 7 hours 30 minutes. Flights with two or more stops can take significantly longer, averaging about 13 hours. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your journey.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Winnipeg, MB (YWG-Winnipeg James Armstrong Richardson Intl.)?
Yes, you can fly business class or first class between ORD and YWG. Airlines that offer business class service on this route include:
  • Air Canada
  • Delta
  • United
First class cabins are available on Delta and United.
How do I earn miles on a Chicago, IL (ORD) to Winnipeg, MB (YWG) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD) to Winnipeg, MB (YWG) 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, MB (YWG) from Chicago, IL (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), or 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) to Winnipeg, MB (YWG) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD) to Winnipeg, MB (YWG) 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) to Winnipeg, MB (YWG) flight and hotel package?
Securing a Chicago, IL (ORD) to Winnipeg, MB (YWG) 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) to Winnipeg, MB (YWG)?
If you booked your Chicago, IL (ORD) to Winnipeg, MB (YWG) 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.
Return price
AU$653
Distance
1130 km
Average flight time
2 hours 38 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 20 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 AU$653 to AU$1,083, 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 August.

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

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