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 — the Rocky Mountain Front Range on departure and the Chicago lakefront skyline on approach. The right side gets flat Nebraska and Iowa farmland for most of the cruise, which is far less visually interesting.

During takeoff from Denver International (DEN), sit on the Left side for the best views. DEN typically departs eastward on runways 25L/25R or westward on 34L/34R. On an eastbound departure toward Chicago, aircraft often use runways oriented east, then bank left (northward) to track toward Illinois. A left seat gives you the Rocky Mountain Front Range — the entire wall from Pikes Peak to Longs Peak — as the plane climbs and turns away from the mountains. Notable sights include: Rocky Mountain Front Range (Pikes Peak to Longs Peak), Denver city grid and downtown skyline, Cherry Creek Reservoir, the flat High Plains stretching east.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Midway typically lands on runways oriented northeast-southwest (runways 31C/31L or 13C/13L). On approach from the west-southwest, a left seat faces north toward downtown Chicago, Lake Michigan, and the lakefront. You get the full Chicago skyline broadside as you descend over the South Side. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago South Side street grid, Soldier Field and Museum Campus area.

The flight from Denver International (DEN) to Chicago Midway International (MDW) takes Approximately 2 hours 15 minutes.

The flight tracks roughly northeast across the High Plains of eastern Colorado, then across Nebraska's flat agricultural landscape bisected by the Platte River valley, then into Iowa's patchwork corn and soybean fields. The Missouri River crossing near Omaha is visible as a distinct dark ribbon cutting through the plains. No significant terrain changes — elevation drops steadily from about 5,000 ft near Denver to near sea level approaching Chicago. The Illinois state line brings denser suburban development visible below.