Sit on the Left side of the plane for the best views on flights from Chicago to Calgary. Left side wins both ends of the flight. At takeoff you get Chicago's skyline and Lake Michigan; at landing you get the full Rocky Mountain panorama. The right side offers flat prairie on approach and suburban Chicago on departure — significantly less dramatic at both ends.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common departures head northwest or west. A left/south-facing seat gives you a clear view back over Chicago's downtown skyline and Lake Michigan as you climb out. You can see the distinct grid of the city, Grant Park, and the lakefront clearly before turning northwest. Notable sights include: Chicago downtown skyline and Willis Tower, Lake Michigan shoreline, Grant Park and Museum Campus, O'Hare's own massive runway complex.

When landing at Calgary International (YYC), sit on the Left side for the best views. Calgary's most common approaches are from the south or east, meaning the aircraft typically arrives heading north or northwest. A left/west-facing seat gives you the best view of the Rocky Mountain Front Ranges — the Bow Valley, Mount Rundle, and the dramatic wall of peaks west of Calgary — as you descend. The right side faces east toward the flat prairie. Notable sights include: Rocky Mountain Front Ranges west of Calgary, Bow River valley, Mount Rundle near Canmore, City of Calgary and its downtown core.

The flight from Chicago Ohare International (ORD) to Calgary International (YYC) takes Approximately 3 hours 15 minutes to 3 hours 45 minutes.

The flight tracks northwest over Wisconsin, crossing the Mississippi River near La Crosse, then over Minnesota's lake-dotted landscape, across the flat agricultural plains of North Dakota and into Saskatchewan. The terrain is predominantly flat prairie for the majority of the cruise phase, with the Missouri River visible in North Dakota. The landscape transitions from green farmland to drier brown prairie as you cross into Canada. The dramatic change comes in the final 30-40 minutes as the Rocky Mountain foothills appear on the western horizon and the Front Ranges build into view on descent into Calgary.