Cheap flights from Chicago to Collingwood

View AU$105 flight on Fri, 17 Oct. 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
Fri, 17 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$274 Return, found 6 hours ago
AU$274
Return
found 6 hours ago
Select United flight, departing Fri, 17 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$274 found 6 hours ago
United
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
YYZ
Toronto
AU$276 Return, found 2 days ago
AU$276
Return
found 2 days ago
Select United flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Wed, 17 Sep., priced at AU$276 found 2 days ago
Air Canada
Fri, 17 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$283 Return, found 6 hours ago
AU$283
Return
found 6 hours ago
Select Air Canada flight, departing Fri, 17 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$283 found 6 hours ago
Delta
Thu, 4 Sep. - Wed, 10 Sep.
ORD
Chicago
YYZ
Toronto
AU$309 Return, found 8 hours ago
AU$309
Return
found 8 hours ago
Select Delta flight, departing Thu, 4 Sep. from Chicago to Toronto, returning Wed, 10 Sep., priced at AU$309 found 8 hours ago
American Airlines
Fri, 17 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$323 Return, found 6 hours ago
AU$323
Return
found 6 hours ago
Select American Airlines flight, departing Fri, 17 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$323 found 6 hours ago
WestJet
Wed, 20 Aug. - Sun, 31 Aug.
ORD
Chicago
YYZ
Toronto
AU$501 Return, found 5 hours ago
AU$501
Return
found 5 hours ago
Select WestJet flight, departing Wed, 20 Aug. from Chicago to Toronto, returning Sun, 31 Aug., priced at AU$501 found 5 hours 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.