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

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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 $563 round trip and CA $235 one way. Prices and availability subject to change. Additional terms may apply.

Thu, Sep 24 - Fri, Oct 2
ORD
Chicago
YWG
Winnipeg
CA $563 Roundtrip, found 5 days ago
CA $563
Roundtrip
found 5 days ago
Select WestJet flight, departing Thu, Sep 24 from Chicago to Winnipeg, returning Fri, Oct 2, priced at CA $563 found 5 days ago
Thu, Sep 24 - Fri, Oct 2
ORD
Chicago
YWG
Winnipeg
CA $566 Roundtrip, found 5 days ago
CA $566
Roundtrip
found 5 days ago
Select WestJet flight, departing Thu, Sep 24 from Chicago to Winnipeg, returning Fri, Oct 2, priced at CA $566 found 5 days ago
Fri, Sep 18 - Fri, Sep 25
ORD
Chicago
YWG
Winnipeg
CA $587 Roundtrip, found 3 days ago
CA $587
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 18 from Chicago to Winnipeg, returning Fri, Sep 25, priced at CA $587 found 3 days ago
Mon, Oct 19 - Fri, Oct 23
ORD
Chicago
YWG
Winnipeg
CA $591 Roundtrip, found 4 days ago
CA $591
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Oct 19 from Chicago to Winnipeg, returning Fri, Oct 23, priced at CA $591 found 4 days ago
Sun, Sep 20 - Tue, Sep 29
ORD
Chicago
YWG
Winnipeg
CA $593 Roundtrip, found 14 hours ago
CA $593
Roundtrip
found 14 hours ago
Select WestJet flight, departing Sun, Sep 20 from Chicago to Winnipeg, returning Tue, Sep 29, priced at CA $593 found 14 hours ago
Mon, Oct 19 - Fri, Oct 23
ORD
Chicago
YWG
Winnipeg
CA $594 Roundtrip, found 4 days ago
CA $594
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Oct 19 from Chicago to Winnipeg, returning Fri, Oct 23, priced at CA $594 found 4 days ago
Fri, Oct 16 - Sun, Oct 18
ORD
Chicago
YWG
Winnipeg
CA $594 Roundtrip, found 19 hours ago
CA $594
Roundtrip
found 19 hours ago
Select WestJet flight, departing Fri, Oct 16 from Chicago to Winnipeg, returning Sun, Oct 18, priced at CA $594 found 19 hours ago
Fri, Sep 18 - Fri, Sep 25
ORD
Chicago
YWG
Winnipeg
CA $597 Roundtrip, found 3 days ago
CA $597
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Sep 18 from Chicago to Winnipeg, returning Fri, Sep 25, priced at CA $597 found 3 days ago
Fri, Sep 18 - Fri, Sep 25
ORD
Chicago
YWG
Winnipeg
CA $619 Roundtrip, found 3 days ago
CA $619
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 18 from Chicago to Winnipeg, returning Fri, Sep 25, priced at CA $619 found 3 days ago
Thu, Sep 24 - Fri, Oct 2
ORD
Chicago
YWG
Winnipeg
CA $625 Roundtrip, found 5 days ago
CA $625
Roundtrip
found 5 days ago
Select WestJet flight, departing Thu, Sep 24 from Chicago to Winnipeg, returning Fri, Oct 2, priced at CA $625 found 5 days ago

Winnipeg James Armstrong Richardson Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Canad Inns Destination Centre Garden City

Canad Inns Destination Centre Garden City

3 out of 5
Price was CA $708, price is now CA $679 per person
CA $679
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Winnipeg (YWG)
Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
Price was CA $894, price is now CA $795 per person
CA $795
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Winnipeg (YWG)
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Price was CA $833, price is now CA $759 per person
CA $759
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Winnipeg (YWG)
Inn At The Forks

Inn At The Forks

3.5 out of 5
Price was CA $1,380, price is now CA $1,288 per person
CA $1,288
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Winnipeg (YWG)
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
Price was CA $840, price is now CA $790 per person
CA $790
per person
Oct 5 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Winnipeg (YWG)
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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.

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*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.