$194 Cheap Air Canada flights from Winnipeg to Chicago (YWG to ORD)

Find The Best Day To Fly from Winnipeg to Chicago

Amazing Air Canada YWG to ORD Flight Deals

The cheapest flights to O'Hare Intl. found within the past 7 days were $372 round trip and $194 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Aug 8 - Sun, Aug 10
YWG
Winnipeg
ORD
Chicago
$372 Roundtrip, found 4 days ago
$372
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Aug 8 from Winnipeg to Chicago, returning Sun, Aug 10, priced at $372 found 4 days ago
Fri, Aug 8 - Sun, Aug 10
YWG
Winnipeg
ORD
Chicago
$406 Roundtrip, found 4 days ago
$406
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Aug 8 from Winnipeg to Chicago, returning Sun, Aug 10, priced at $406 found 4 days ago
Fri, Aug 8 - Sun, Aug 10
YWG
Winnipeg
ORD
Chicago
$424 Roundtrip, found 4 days ago
$424
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Aug 8 from Winnipeg to Chicago, returning Sun, Aug 10, priced at $424 found 4 days ago
Sun, Aug 24 - Mon, Aug 25
YWG
Winnipeg
ORD
Chicago
$426 Roundtrip, found 6 hours ago
$426
Roundtrip
found 6 hours ago
Select Air Canada flight, departing Sun, Aug 24 from Winnipeg to Chicago, returning Mon, Aug 25, priced at $426 found 6 hours ago
Fri, Aug 8 - Sun, Aug 10
YWG
Winnipeg
ORD
Chicago
$429 Roundtrip, found 4 days ago
$429
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Aug 8 from Winnipeg to Chicago, returning Sun, Aug 10, priced at $429 found 4 days ago
Sun, Aug 24 - Mon, Aug 25
YWG
Winnipeg
ORD
Chicago
$435 Roundtrip, found 6 hours ago
$435
Roundtrip
found 6 hours ago
Select Air Canada flight, departing Sun, Aug 24 from Winnipeg to Chicago, returning Mon, Aug 25, priced at $435 found 6 hours ago

Frequently asked questions

Can I catch a flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to ORD right now?
For info on any present O'Hare Airport quarantine requirements and travel advice, go to the Covid-19 Travel Advisor. Look before you book your flight, so you don't get caught up en route.
What terminal is Air Canada at YWG?
Once you receive the boarding pass for your Air Canada flight from Winnipeg Airport to O'Hare Airport, you should be able to determine which terminals you'll be flying in and out of. Your carrier will have the answers if those details are missing from your ticket.
Are there Air Canada non-stop flights from YWG to ORD?
You won't be able to fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Intl. Airport (ORD) with Air Canada. You should be prepared to make at least one stopover if you need to stick to this route and airline.
How long is an Air Canada flight from YWG to ORD?
Watch your favorite TV show, listen to some music or just put your seat back and forget your worries. You'll need to find a way to entertain yourself during the 4 hours and 34 minutes that it takes to venture from YWG to ORD with Air Canada.
How many direct and indirect flights does Air Canada fly from YWG to ORD?
If you need to book a trip from YWG to ORD, you can select from roughly 5 Air Canada flights every day.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to O'Hare Airport, please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Discover our best Air Canada flight from Winnipeg YWG to Chicago ORD 

To find the best deals on flights to Winnipeg from Chicago with Air Canada, just enter your travel dates, filter by Air Canada, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Winnipeg YWG to Chicago ORD with Air Canada 

If you’re planning a round trip, booking return flights with Air Canada is usually the most cost-effective option. With airfares ranging from $372 to $435, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way Air Canada flights from Winnipeg YWG to Chicago ORD 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way Air Canada flight from Winnipeg to Chicago costs from $194. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to Chicago ORD from  Winnipeg YWG with Air Canada 

To find a cheap Air Canada flight from Winnipeg YWG to Chicago ORD, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on Air Canada flights from Winnipeg YWG to Chicago ORD 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as August, or if you book a flight with a stopover. 

 

Find nonstop flights from Winnipeg YWG to Chicago ORD with Air Canada 

If you’re keen to be on Chicago soil fast, don’t waste time with a stopover—filter your search results to show direct Air Canada flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for Air Canada flights from Winnipeg YWG to Chicago ORD 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to Chicago ORD from  Winnipeg YWG with Air Canada on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

Air Canada Airports
Hop on a(n) Air Canada flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
ORDUSAO'Hare Intl.81
DENUSADenver Intl.79
IAHUSAGeorge Bush Intercontinental43
YYZCANPearson Intl.38
SFOUSASan Francisco Intl.29
IADUSAWashington Dulles Intl.22
YVRCANVancouver Intl.22
FRADEUFrankfurt Intl.15
YULCANPierre Elliott Trudeau Intl.15
HNDJPNHaneda10

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