Sit on the Right side of the plane for the best views on flights from Chicago to Colorado Springs. While the left side wins at takeoff for the Chicago skyline view, the right side delivers the more spectacular payoff: the entire westward flight gives you the gradual transition from Great Plains to the Rocky Mountain Front Range, culminating in the Pikes Peak approach on landing. The mountain scenery on the right during descent is the highlight of this route.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common westbound departures use runways 10L/10R or 28L/28R. On a westbound departure heading toward Colorado, the left side gives you a clear view south over downtown Chicago's skyline and Lake Michigan's shoreline as you climb out. The Willis Tower and the lakefront are unmistakable from the left window during the initial climb. Notable sights include: Downtown Chicago skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River corridor, Midway Airport to the south.

When landing at City Of Colorado Springs Muni (COS), sit on the Right side for the best views. Colorado Springs Airport typically uses runway 35L/35R for northbound landings or runway 17 for southbound, but the dominant approach is from the south on runway 35, meaning the aircraft tracks northward on final. On this approach, the right side faces west directly toward Pikes Peak and the Front Range, giving you a dramatic straight-on view of the mountains during the entire descent. The left side looks east over the flat plains with little of interest. Notable sights include: Pikes Peak (14,115 ft), Front Range of the Rocky Mountains, Garden of the Gods red rock formations, Colorado Springs urban grid.

The flight from Chicago Ohare International (ORD) to City Of Colorado Springs Muni (COS) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight crosses the flat agricultural grid of northern Illinois, then Iowa and Nebraska cornfields and river valleys, before the terrain begins its gradual rise across eastern Colorado. The South Platte River valley becomes visible as you enter Colorado, and the dramatic transition from the Great Plains to the Rocky Mountain Front Range is visible roughly 30-40 minutes before landing.