Sit on the Left side of the plane for the best views on flights from Denver to Chicago. Left side wins both ends of the flight. At departure you get the Rocky Mountain Front Range panorama, and at arrival you get the Chicago lakefront and Loop skyline. The right side offers flat plains on departure and suburban sprawl on arrival — no contest.

During takeoff from Denver International (DEN), sit on the Left side for the best views. DEN typically departs eastward on runways 25L/25R or northeastward on 34L/34R. On an eastbound departure climbing out, the left (north) side gives you a clear look back at the Front Range of the Rockies as you bank northeast. The entire stretch from Longs Peak down through the Denver metro foothills is laid out clearly on the left side during the initial climb and turn. Notable sights include: Front Range of the Rocky Mountains (Longs Peak, Mount Evans visible), Denver city grid and downtown skyline, Cherry Creek Reservoir southeast of the city, the flat checkerboard of the Colorado plains stretching east.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Flights from Denver approach ORD typically from the southwest, and O'Hare most commonly uses runways oriented east-west (10/28 complex) or northwest-southeast (32L/32R). On a southwest approach to ORD, the left side faces south over the Chicago metro, giving you a clear view of the lakefront, the downtown Loop skyline, and Lake Michigan. The right side faces northwest toward suburban sprawl with no comparable landmarks. Notable sights include: Lake Michigan shoreline and the Chicago Loop skyline, Grant Park and the Museum Campus peninsula, Midway Airport visible to the south, the dense urban grid of Chicago's South and West sides.

The flight from Denver International (DEN) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks northeast across the Nebraska Sandhills — a vast, lightly populated grass-covered dune landscape — then crosses the Missouri River near Omaha or Council Bluffs, followed by the flat agricultural grid of Iowa cornfields and the Mississippi River near the Quad Cities before entering Illinois and the Chicago metro area.