Cheap Flights From O'Hare Intl. (ORD) To Winnipeg James Armstrong Richardson Intl. (YWG)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

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

The cheapest flights to Winnipeg James Armstrong Richardson Intl. found within the past 7 days were CA $573 round trip and CA $239 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Sep. 20 - Fri, Sep. 26
ORD
Chicago
YWG
Winnipeg
CA $573 Roundtrip, found 1 day ago
CA $573
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Sep. 20 from Chicago to Winnipeg, returning Fri, Sep. 26, priced at CA $573 found 1 day ago
Sat, Sep. 20 - Fri, Sep. 26
ORD
Chicago
YWG
Winnipeg
CA $626 Roundtrip, found 1 day ago
CA $626
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Sep. 20 from Chicago to Winnipeg, returning Fri, Sep. 26, priced at CA $626 found 1 day ago
Thu, Sep. 18 - Wed, Sep. 24
ORD
Chicago
YWG
Winnipeg
CA $635 Roundtrip, found 6 days ago
CA $635
Roundtrip
found 6 days ago
Select WestJet flight, departing Thu, Sep. 18 from Chicago to Winnipeg, returning Wed, Sep. 24, priced at CA $635 found 6 days ago
Sat, Sep. 20 - Fri, Sep. 26
ORD
Chicago
YWG
Winnipeg
CA $663 Roundtrip, found 2 days ago
CA $663
Roundtrip
found 2 days ago
Select WestJet flight, departing Sat, Sep. 20 from Chicago to Winnipeg, returning Fri, Sep. 26, priced at CA $663 found 2 days ago
Thu, Sep. 18 - Wed, Sep. 24
ORD
Chicago
YWG
Winnipeg
CA $671 Roundtrip, found 2 days ago
CA $671
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Sep. 18 from Chicago to Winnipeg, returning Wed, Sep. 24, priced at CA $671 found 2 days ago
Thu, Sep. 18 - Wed, Sep. 24
ORD
Chicago
YWG
Winnipeg
CA $671 Roundtrip, found 6 days ago
CA $671
Roundtrip
found 6 days ago
Select WestJet flight, departing Thu, Sep. 18 from Chicago to Winnipeg, returning Wed, Sep. 24, priced at CA $671 found 6 days ago
Fri, Sep. 5 - Mon, Sep. 8
ORD
Chicago
YWG
Winnipeg
CA $706 Roundtrip, found 1 day ago
CA $706
Roundtrip
found 1 day ago
Select WestJet flight, departing Fri, Sep. 5 from Chicago to Winnipeg, returning Mon, Sep. 8, priced at CA $706 found 1 day ago
Thu, Sep. 18 - Wed, Sep. 24
ORD
Chicago
YWG
Winnipeg
CA $708 Roundtrip, found 2 days ago
CA $708
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Sep. 18 from Chicago to Winnipeg, returning Wed, Sep. 24, priced at CA $708 found 2 days ago
Thu, Sep. 18 - Wed, Sep. 24
ORD
Chicago
YWG
Winnipeg
CA $711 Roundtrip, found 2 days ago
CA $711
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Sep. 18 from Chicago to Winnipeg, returning Wed, Sep. 24, priced at CA $711 found 2 days ago
Fri, Sep. 5 - Mon, Sep. 8
ORD
Chicago
YWG
Winnipeg
CA $715 Roundtrip, found 1 day ago
CA $715
Roundtrip
found 1 day ago
Select WestJet flight, departing Fri, Sep. 5 from Chicago to Winnipeg, returning Mon, Sep. 8, priced at CA $715 found 1 day ago

Frequently asked questions

Are there direct flights from O'Hare Airport to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Air Canada, United Airlines and WestJet will fly you to Winnipeg from Chicago with one stopover. Unfortunately, there are no direct flights between O'Hare Airport and Winnipeg Airport just yet.
What airlines fly from O'Hare Airport to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
When traveling from ORD to YWG, it's best to plan ahead — no direct flights are currently available. Booking well in advance should help you find the ideal price and route.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca 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 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago (ORD) today with the cheap prices from Travelocity!

Popular Flight Routes from Winnipeg (YWG)

Travelers at YWG love to visit these top cities. Roam to the top destinations from Winnipeg(YWG) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.