Flight Routes from Toronto to Chicago Midway

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

Trip type
Fastest flight
non-stop flights
31x / week
Flight distance
715 km
Time difference
Airports in Toronto
  1. Lester B. Pearson International Airport
  2. Hamilton
  3. Kitchener/Waterloo
  4. City Centre Airport

Flight schedule from Toronto (YTO) to Chicago Midway (MDW)

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

offers
Active filtersnone
Matching outbound flights3 of 3
fromto
dep.arr.
durationstopovers
  1. September 6 – 12, 2026
  2. September 13 – 19, 2026
  3. September 20 – 26, 2026
    No flights could be found for the active filters.
    1. YTZMDW
      nonstop
      1. Porter Airlines
    2. YTZMDW
      nonstop
      1. Porter Airlines
    3. YTZMDW
      nonstop
      1. Porter Airlines

      Important flight information

      Discover more flights around Toronto and Chicago Midway

      Departure airport Airport Toronto (YTO)
      Departure country Flights from Canada
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure country - Arrival airport Canada - Chicago Midway International Airport, IL
      Departure airport - Destination country Toronto - United States
      Departure airport - City-Code Toronto - Chicago