Sit on the Left side of the plane for the best views on flights from Chicago to Denver. The left side misses the Chicago departure views but wins decisively on the landing approach with the full Front Range panorama. Across the cruise portion heading west-southwest, the left side also gets better angles on the Nebraska Sandhills and early Colorado terrain. The Rocky Mountain arrival view on the left is the highlight of this route.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. MDW typically departs westbound on runway 31C/31R, so the right side faces south toward the Chicago lakefront and downtown skyline during the climbing turn. You get a clear view of the Loop skyscrapers and the southern lakefront before the aircraft tracks west. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Soldier Field, Chicago Southside neighborhoods.

When landing at Denver International (DEN), sit on the Left side for the best views. DEN primarily lands from the east on runways 34L/35L/36L heading northwest, or from the south on runway 17. On the common easterly approach, the left side faces west and southwest, giving a prolonged view of the entire Front Range including Pikes Peak, Longs Peak, and the Denver metro spread below the mountains. Notable sights include: Front Range of the Rocky Mountains, Pikes Peak, Longs Peak, Denver metro grid.

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

The flight tracks west-southwest over the flat Illinois and Iowa farmland, then crosses the Missouri River near Omaha. Over Nebraska the terrain remains flat but the Platte River valley is visible below. Approaching eastern Colorado the land rises subtly onto the high plains, and the Rocky Mountain Front Range becomes visible on the horizon roughly 100 miles out from Denver, gradually resolving from a faint blue line into distinct snow-capped peaks.