Sit on the Left side of the plane for the best views on flights from Colorado Springs to Chicago. Left side wins both ends of the flight. At takeoff you get the full Rocky Mountain Front Range and Pikes Peak broadside, and at landing you get the Chicago lakefront and downtown skyline. The right side offers plains and suburban sprawl at both ends.

During takeoff from City Of Colorado Springs Muni (COS), sit on the Left side for the best views. Colorado Springs runways typically favor departures to the north or south. On a northeastbound departure toward Chicago, the left (west) side gives you a direct broadside view of Pikes Peak and the Front Range. The mountain wall is immediately visible and dramatic during climb-out before the aircraft turns east. Notable sights include: Pikes Peak (14,115 ft), Front Range of the Rockies, Garden of the Gods red rock formations below, Palmer Lake reservoir to the north.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals from the west typically use runways oriented east-west or northwest-southeast. On approach from the southwest, the left (south) side gives you Lake Michigan's shoreline, the Chicago downtown skyline, and the lakefront grid. The right side faces northwest toward suburban sprawl with little of interest. Notable sights include: Lake Michigan shoreline and lakefront, Chicago downtown skyline (Willis Tower, John Hancock), O'Hare airport layout visible on final, suburban grid of the Chicago metro.

The flight from City Of Colorado Springs Muni (COS) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes to 2 hours 40 minutes.

The flight crosses the high plains of eastern Colorado and Kansas, passing over the Arkansas River valley near Pueblo, then the flat agricultural checkerboard of central Kansas and Missouri. Around the Kansas-Missouri border you may see the Missouri River as a winding brown ribbon. The flight then crosses central Illinois farmland before descending into Chicago. No significant terrain features mid-flight — this is genuinely flat Great Plains and Midwest agricultural land at cruise altitude.