Cheap flights from Chicago to Collingwood

View AU$105 flight on Mon, 8 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
Mon, 8 Sep. - Mon, 15 Sep.
ORD
Chicago
YYZ
Toronto
AU$276 Return, just found
AU$276
Return
just found
Select United flight, departing Mon, 8 Sep. from Chicago to Toronto, returning Mon, 15 Sep., priced at AU$276 just found
United
Wed, 1 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$277 Return, found 21 hours ago
AU$277
Return
found 21 hours ago
Select United flight, departing Wed, 1 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$277 found 21 hours ago
Air Canada
Mon, 8 Sep. - Mon, 15 Sep.
ORD
Chicago
YYZ
Toronto
AU$284 Return, just found
AU$284
Return
just found
Select Air Canada flight, departing Mon, 8 Sep. from Chicago to Toronto, returning Mon, 15 Sep., priced at AU$284 just found
Delta
Wed, 1 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$312 Return, found 21 hours ago
AU$312
Return
found 21 hours ago
Select Delta flight, departing Wed, 1 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$312 found 21 hours ago
American Airlines
Fri, 7 Nov. - Wed, 12 Nov.
ORD
Chicago
YYZ
Toronto
AU$335 Return, found 6 days ago
AU$335
Return
found 6 days ago
Select American Airlines flight, departing Fri, 7 Nov. from Chicago to Toronto, returning Wed, 12 Nov., priced at AU$335 found 6 days ago
WestJet
Wed, 10 Sep. - Sat, 13 Sep.
ORD
Chicago
YYZ
Toronto
AU$507 Return, found 22 hours ago
AU$507
Return
found 22 hours ago
Select WestJet flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Sat, 13 Sep., priced at AU$507 found 22 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.