Sit on the Left side of the plane for the best views on flights from Chicago to Toronto. While the right side has a good Chicago departure view, the left side delivers the more dramatic payoff: a close-range approach into Billy Bishop with the CN Tower and Toronto skyline filling the window at low altitude over Lake Ontario. The left side also tracks the southern shore of Lake Erie and Lake Ontario during cruise, offering continuous water views.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. O'Hare's most common departure heading for eastbound flights is on runways 10R/10L (heading roughly east), meaning the right side faces north toward the Chicago suburbs and eventually Lake Michigan's southern shoreline. As the aircraft climbs and turns northeast toward Toronto, the right side picks up the Chicago skyline and the lakefront. Notable sights include: Chicago downtown skyline to the southeast, Lake Michigan shoreline, O'Hare's sprawling runway complex below, northern Chicago suburbs grid.

When landing at City Centre (YTZ), sit on the Left side for the best views. Billy Bishop (YTZ) sits on the Toronto Islands, and aircraft typically approach from the west over Lake Ontario on runway 26, meaning the left side faces south over the lake and then swings to show the Toronto downtown skyline — CN Tower, Rogers Centre, and the waterfront — at close range during final approach. Notable sights include: CN Tower and Toronto downtown skyline, Lake Ontario, Toronto Islands and harbour, Rogers Centre.

The flight from Chicago Ohare International (ORD) to City Centre (YTZ) takes Approximately 1 hour to 1 hour 15 minutes.

The flight tracks northeast across northern Indiana and southern Michigan, crossing Lake Erie's western basin near the Ontario-Ohio border. Passengers can see the flat agricultural patchwork of southwestern Ontario before descending over Lake Ontario toward Toronto. The north shore of Lake Erie is visible during cruise, and on clear days the Detroit metro area may be visible to the northwest early in the flight.