Cheap flights from Winnipeg to Northwest Chicago

View AU$305 flight on Thu, 4 Sep. 2025Opens in a new window

Popular airlines from Winnipeg to Northwest Chicago

  • Air Canada

    Air Canada

  • Delta

    Delta

  • United

    United

  • WestJet

    WestJet

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Cheap Flights from Winnipeg (YWG) to Northwest Chicago (CHI)

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.

Air Canada
Thu, 4 Sep. - Sun, 7 Sep.
YWG
Winnipeg
ORD
Chicago
AU$545 Return, found 10 hours ago
AU$545
Return
found 10 hours ago
Select Air Canada flight, departing Thu, 4 Sep. from Winnipeg to Chicago, returning Sun, 7 Sep., priced at AU$545 found 10 hours ago
United
Thu, 4 Sep. - Sun, 7 Sep.
YWG
Winnipeg
ORD
Chicago
AU$545 Return, found 10 hours ago
AU$545
Return
found 10 hours ago
Select United flight, departing Thu, 4 Sep. from Winnipeg to Chicago, returning Sun, 7 Sep., priced at AU$545 found 10 hours ago
United
Thu, 4 Sep. - Sun, 7 Sep.
YWG
Winnipeg
ORD
Chicago
AU$554 Return, found 10 hours ago
AU$554
Return
found 10 hours ago
Select United flight, departing Thu, 4 Sep. from Winnipeg to Chicago, returning Sun, 7 Sep., priced at AU$554 found 10 hours ago
Air Canada
Thu, 4 Sep. - Sun, 7 Sep.
YWG
Winnipeg
ORD
Chicago
AU$555 Return, found 10 hours ago
AU$555
Return
found 10 hours ago
Select Air Canada flight, departing Thu, 4 Sep. from Winnipeg to Chicago, returning Sun, 7 Sep., priced at AU$555 found 10 hours ago
WestJet
Thu, 4 Sep. - Sun, 7 Sep.
YWG
Winnipeg
ORD
Chicago
AU$594 Return, found 10 hours ago
AU$594
Return
found 10 hours ago
Select WestJet flight, departing Thu, 4 Sep. from Winnipeg to Chicago, returning Sun, 7 Sep., priced at AU$594 found 10 hours ago
Delta
Thu, 4 Sep. - Sun, 7 Sep.
YWG
Winnipeg
ORD
Chicago
AU$609 Return, found 10 hours ago
AU$609
Return
found 10 hours ago
Select Delta flight, departing Thu, 4 Sep. from Winnipeg to Chicago, returning Sun, 7 Sep., priced at AU$609 found 10 hours ago

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

June is typically the cheapest month to fly

From AU$369 - AU$745 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.