Cheap flights from Toronto to Chicago from CA $194

Cheap flights from Toronto (YTO) to Chicago (CHI)

Prices were available within the past 7 days and start at CA $194 for one-way flights and CA $337 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon., May 6 - Wed., May 22

YTZ

Toronto

MDW

Chicago

CA $337 Roundtrip, found 3 days ago

CA $337

Roundtrip

found 3 days ago

Select Porter Airlines flight, departing Mon., May 6 from Toronto to Chicago, returning Wed., May 22, priced at CA $337 found 3 days ago

Sat., May 11 - Sun., May 12

YYZ

Toronto

ORD

Chicago

CA $337 Roundtrip, just found

CA $337

Roundtrip

just found

Select American Airlines flight, departing Sat., May 11 from Toronto to Chicago, returning Sun., May 12, priced at CA $337 just found

Wed., May 8 - Wed., May 15

YYZ

Toronto

ORD

Chicago

CA $339 Roundtrip, found 1 day ago

CA $339

Roundtrip

found 1 day ago

Select Air Canada flight, departing Wed., May 8 from Toronto to Chicago, returning Wed., May 15, priced at CA $339 found 1 day ago

Fri., May 24 - Fri., May 31

YTZ

Toronto

MDW

Chicago

CA $343 Roundtrip, found 1 day ago

CA $343

Roundtrip

found 1 day ago

Select Porter Airlines flight, departing Fri., May 24 from Toronto to Chicago, returning Fri., May 31, priced at CA $343 found 1 day ago

Fri., May 10 - Sun., May 12

YYZ

Toronto

ORD

Chicago

CA $345 Roundtrip, just found

CA $345

Roundtrip

just found

Select American Airlines flight, departing Fri., May 10 from Toronto to Chicago, returning Sun., May 12, priced at CA $345 just found

Sun., May 12 - Mon., May 13

YYZ

Toronto

ORD

Chicago

CA $347 Roundtrip, just found

CA $347

Roundtrip

just found

Select American Airlines flight, departing Sun., May 12 from Toronto to Chicago, returning Mon., May 13, priced at CA $347 just found