Calgary to Chicago flight path: YYC to ORD

Sit on the Left side of the plane for the best views on flights from Calgary to Chicago. The left side wins because the Rocky Mountain departure view is far more dramatic and immersive than the brief, hazy skyline glimpse on landing, and the cruise phase over the Great Plains offers little scenery on either side to offset that advantage.

During takeoff from Calgary International (YYC), sit on the Left side for the best views. Calgary departures typically launch north on runway 35 before turning toward Chicago, and during that initial climb the Rocky Mountain front range dominates the western horizon on the left side. The Bow River valley and foothills give way to the snow-capped peaks near Banff before the aircraft turns east and the mountains fall away. Notable sights include: Canadian Rocky Mountains front range, Bow River valley, Banff-area peaks, Calgary foothills.

When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. On approach into O'Hare from the west, the flight path passes north of downtown, so passengers on the right side facing south get a distant but recognizable view of the Chicago skyline before touchdown. The left side only shows flat farmland and suburban grids with no distinguishing features. Notable sights include: Chicago downtown skyline (distant), western suburban grid streets, flat Illinois farmland, occasional small lakes.

The flight from Calgary International (YYC) to Chicago Ohare International (ORD) takes 2h 50m.

Flat plains of Montana and North Dakota, the Missouri River near Williston, and the farmland mosaic of Minnesota and Wisconsin before the descent into the Chicago area