Sit on the Right side of the plane for the best views on flights from Chicago to St. Louis. Right-side seats win overall because the takeoff view of Chicago's skyline and Lake Michigan is more visually distinctive than the landing approach. While the Gateway Arch is iconic, the Chicago departure offers a longer, more detailed urban geography lesson.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats capture the Chicago skyline and Lake Michigan as you climb out. Midway typically departs runways 31L/31R heading northwest, which angles your initial climb toward downtown Chicago and the lakefront. Notable sights include: Chicago downtown skyline (Willis Tower, Trump Tower visible as white spire), Lake Michigan shoreline, Bridgeport neighborhood industrial areas, Des Plaines River bend.

When landing at Lambert St Louis International (STL), sit on the Left side for the best views. Left-side seats offer views of the Mississippi River and St. Louis's Gateway Arch as you descend into Lambert. Typical landing approaches use runways 30L/30R from the northeast, positioning the river and arch on your left during the final approach. Notable sights include: Mississippi River (wide, meandering), Gateway Arch (distinctive stainless steel curve), downtown St. Louis skyline, Illinois bluffs across the river.

The flight from Chicago Midway International (MDW) to Lambert St Louis International (STL) takes Approximately 1 hour 15 minutes.

The flight path crosses central Illinois, passing over the Illinois prairie and scattered farmland. Notable features include the Sangamon River valley near Springfield (visible as a darker green corridor through agricultural land), and the transition from Illinois's flat terrain to the slightly rolling topography approaching the Mississippi River bluffs. No major mountain ranges or dramatic terrain—this is a low-relief corridor over the American Corn Belt.