Sit on the Left side of the plane for the best views on flights from Chicago to Toronto. While the right side wins at departure with Chicago's skyline, the left side delivers the more dramatic arrival sequence — Lake Ontario, the CN Tower, and Toronto's waterfront on descent are genuinely spectacular. For the cruise phase heading northeast, the left side also faces generally toward Lake Michigan's northern reaches and Georgian Bay, giving more water and landscape interest than the right.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. O'Hare departures heading east toward Toronto typically use runways oriented east-northeast. The right side gives you a clear view south over Chicago's dense urban grid, the lakefront, and downtown skyline as you climb out. The left side faces north toward suburban sprawl with far less visual interest. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Grant Park and Museum Campus, Chicago River grid pattern.

When landing at Lester B Pearson International (YYZ), sit on the Left side for the best views. Pearson's most common arrival runways from the west bring aircraft in from the northwest on headings roughly toward the southeast. The left side faces northeast, giving a clear view of Lake Ontario, the Toronto waterfront, and the downtown skyline including the CN Tower as you descend. The right side faces southwest into suburban Mississauga with little of note. Notable sights include: CN Tower and Toronto downtown skyline, Lake Ontario, Toronto Islands, Mississauga suburban sprawl.

The flight from Chicago Ohare International (ORD) to Lester B Pearson International (YYZ) takes Approximately 1 hour 10 minutes to 1 hour 25 minutes.

The flight crosses southern Lake Michigan or skirts its southern shore depending on routing, then passes over southwestern Ontario — a flat agricultural landscape of fields and small towns. Lake Erie may be visible to the south in the distance. The Grand River valley in Ontario is crossed before descent into Toronto. No significant terrain — this is a low, flat route throughout.