Flight Routes from Toronto to Chicago

Compare cheap outbound and return flights from Toronto (YYZ) to Chicago (CHI) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
131x / week
Flight distance
683 km
Time difference
Airports in Chicago
  1. O'Hare
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Toronto (YYZ) to Chicago (CHI)

Select a travel date in the flight schedule for the route from Toronto (YYZ) to Chicago (CHI) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsYYZ–CHI · 32 of 32
fromto
dep.arr.
durationstopovers
  1. 14 – 20 September 2026
  2. 21 – 27 September 2026
  3. 28 Sept – 4 Oct 2026
    1. YYZORD
      non-stop
      1. American Airlines
    2. YYZORD
      non-stop
      1. American Airlines
    3. YYZORD
      non-stop
      1. United Airlines
    4. YYZORD
      non-stop
      1. Air Canada
    5. YYZORD
      non-stop
      1. United Airlines
    6. YYZORD
      non-stop
      1. United Airlines
    7. YYZORD
      non-stop
      1. United Airlines
    8. YYZORD
      non-stop
      1. United Airlines
    9. YYZORD
      non-stop
      1. United Airlines
    10. YYZORD
      non-stop
      1. American Airlines
    11. YYZORD
      non-stop
      1. Air Canada
    12. YYZORD
      non-stop
      1. Air Canada
    13. YYZORD
      non-stop
      1. United Airlines
    14. YYZORD
      non-stop
      1. American Airlines
    15. YYZORD
      non-stop
      1. American Airlines

      Important flight information

      Discover more flights around Toronto and Chicago

      Departure airport Airport Toronto Pearson (YYZ)
      Departure country Flights from Canada
      Arrival airport Airport Chicago IL all Airports (ORD, MDW, RFD) (CHI)
      Destination country Flights to United States
      Departure country - Arrival airport Canada - Chicago IL all Airports (ORD, MDW, RFD)
      City-Code - Arrival airport Toronto - Chicago IL all Airports (ORD, MDW, RFD)
      Departure airport - Destination country Toronto Pearson - United States