Sit on the Left side of the plane for the best views on flights from Calgary to Chicago. Left side wins both ends of the flight. At departure you get the Rockies and Calgary's river valley; at arrival you get Lake Michigan and the Chicago skyline. Over the Great Plains mid-flight both sides are similarly flat, so the left side's advantage at the scenic bookends makes it the clear overall choice.

During takeoff from Calgary International (YYC), sit on the Left side for the best views. YYC's primary departure runways (35L/35R heading north, or 28 heading west) mean a left-side seat faces south or southwest during climbout, giving you a direct view of the Rocky Mountain Front Ranges rising dramatically west of Calgary. The Bow River valley and the city grid are also clearly visible below before you turn southeast toward Chicago. Notable sights include: Rocky Mountain Front Ranges (Kananaskis/Bow Valley corridor), Bow River winding through Calgary, Calgary downtown skyline to the south, Nose Hill Park plateau.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Flights from YYC approach ORD typically from the northwest, and the most common landing runways are 10L/10R or 28L/28R. On a northwest approach, the left side faces south over the Chicago metro, giving clear views of Lake Michigan's shoreline, the downtown Loop skyline, and the lakefront. The right side faces north over suburban sprawl with far less visual interest. Notable sights include: Lake Michigan shoreline and southern lakefront, Chicago Loop skyline (Willis Tower, John Hancock), Midway Airport grid to the south, the flat Illinois suburban grid.

The flight from Calgary International (YYC) to Chicago Ohare International (ORD) takes Approximately 2 hours 45 minutes to 3 hours.

The flight tracks southeast across the Canadian and American Great Plains — Saskatchewan and Montana briefly, then North Dakota, South Dakota, and Minnesota. The terrain is overwhelmingly flat agricultural land with grid-pattern fields, occasional river valleys like the Missouri River, and the Minnesota lake district visible as scattered reflective patches near the end of the plains section before descending into Illinois.