Sit on the Left side of the plane for the best views on flights from Toronto to Chicago. Left side wins at both ends of this short flight. You get Toronto's waterfront and skyline on departure and Chicago's lakefront and Loop on arrival. The flight is brief enough that the midpoint over Lake Erie and Indiana farmland offers little from either side, so the terminal views are what matter most.

During takeoff from Lester B Pearson International (YYZ), sit on the Left side for the best views. YYZ's most common departure is westbound on runway 23 or southbound on 24L/24R, which puts the left side facing south toward Lake Ontario. You get a clear view of the Toronto waterfront, the downtown skyline including the CN Tower, and the lake stretching to the horizon. The right side faces north into suburban sprawl with little of interest. Notable sights include: CN Tower and downtown Toronto skyline, Lake Ontario shoreline and Toronto Islands, Port Credit and Mississauga waterfront, Hamilton Harbour visible to the southwest.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common arrival from the east is on runways 10L/10R or 9L/9R, meaning the aircraft approaches from the east-northeast on a westward heading. The left side faces south, giving views over the Chicago lakefront, Grant Park, the Loop skyline, and Lake Michigan as you descend. The right side faces north into the northern suburbs. Notable sights include: Chicago Loop skyline and Willis Tower, Lake Michigan shoreline and Grant Park, Wrigley Field visible in Lincoln Park area during low approach, O'Hare's distinctive runway layout visible just before touchdown.

The flight from Lester B Pearson International (YYZ) to Chicago Ohare International (ORD) takes Approximately 1 hour to 1 hour 15 minutes.

The flight path crosses over Lake Erie's northern shoreline near Erie PA, then tracks southwest over northern Indiana farmland — flat agricultural grid with little visual drama. On clear days Lake Erie is visible as a broad grey expanse during the early portion of cruise. The Indiana Dunes and southern tip of Lake Michigan may be briefly visible on descent into ORD from the left side.