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Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
11/1Thu
1 stop
8h 37mYKF-ORD
C$ 103
14/12Thu
1 stop
8h 33mYKF-ORD
C$ 130
17/12Sun
2 stops
18h 42mYKF-ORD
C$ 134
7/1Sun
3 stops
39h 20mYKF-ORD
C$ 139
8/1Mon
1 stop
10h 50mYKF-ORD
C$ 143
17/12Sun
3 stops
33h 09mYKF-ORD
C$ 155
17/12Sun
1 stop
8h 33mYKF-ORD
C$ 162
29/12Fri
1 stop
10h 40mYKF-ORD
C$ 257
29/12Fri
1 stop
10h 40mYKF-ORD
C$ 259
8/1Mon
2 stopsWestJet
24h 53mYKF-ORD
C$ 404

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Last minute flights from Kitchener-Waterloo to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
5/12Tue
multi-stop
18h 42mYKF-ORD
10/1Wed
multi-stop
25h 15mORD-YKF
C$ 228
5/12Tue
multi-stop
29h 22mYKF-ORD
10/1Wed
multi-stop
25h 15mORD-YKF
C$ 250
5/12Tue
multi-stop
8h 33mYKF-ORD
10/1Wed
multi-stop
25h 15mORD-YKF
C$ 325

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Toronto Kitchener-Waterloo - Chicago Flights

Departure:

Toronto Kitchener-Waterloo (YKF)Canada

Cabin classes: