Cheap flights from Chicago to Collingwood

View AU$105 flight on Fri, 5 Sep. 2025Opens in a new window

Popular airlines from Chicago to Collingwood

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Cheap Flights from Chicago (CHI) to Collingwood (YYZ)

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.

United
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
YYZ
Toronto
AU$276 Return, found 1 day ago
AU$276
Return
found 1 day ago
Select United flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Wed, 17 Sep., priced at AU$276 found 1 day ago
United
Wed, 1 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$277 Return, found 2 days ago
AU$277
Return
found 2 days ago
Select United flight, departing Wed, 1 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$277 found 2 days ago
Air Canada
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
YYZ
Toronto
AU$284 Return, found 1 day ago
AU$284
Return
found 1 day ago
Select Air Canada flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Wed, 17 Sep., priced at AU$284 found 1 day ago
Delta
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
YYZ
Toronto
AU$311 Return, found 1 day ago
AU$311
Return
found 1 day ago
Select Delta flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Wed, 17 Sep., priced at AU$311 found 1 day ago
American Airlines
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
YYZ
Toronto
AU$324 Return, found 1 day ago
AU$324
Return
found 1 day ago
Select American Airlines flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Wed, 17 Sep., priced at AU$324 found 1 day ago
WestJet
Tue, 11 Nov. - Sat, 15 Nov.
ORD
Chicago
YYZ
Toronto
AU$503 Return, found 1 day ago
AU$503
Return
found 1 day ago
Select WestJet flight, departing Tue, 11 Nov. from Chicago to Toronto, returning Sat, 15 Nov., priced at AU$503 found 1 day ago

Find the cheapest month to fly from Chicago (CHI) to Toronto (YYZ)

September is typically the cheapest month to fly

From AU$216 - AU$773 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.