Sit on the Right side of the plane for the best views on flights from Chicago to St. Louis. The right side misses the Chicago skyline at departure but captures the Mississippi River crossing and the Gateway Arch on approach, which is the single most iconic visual moment of this flight. The flat Illinois farmland in between offers little differentiation by side, so the Arch view on descent tips the balance to the right.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common departure headings are eastward (runway 10) or southward, but the dominant westbound departures on runways 27L/27R/28C put the city of Chicago and Lake Michigan on the left (south) side. As the aircraft climbs and turns southwest toward STL, the left side gets a clear view of the Chicago skyline, the lakefront, and Grant Park before the urban grid gives way to suburban sprawl. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River corridor, suburban Cook County grid.

When landing at Lambert St Louis International (STL), sit on the Right side for the best views. STL typically uses runways 11/29 or 12L/30R. On a southwest approach (runway 12L or 11), the aircraft descends from the northeast, putting the Mississippi River and the Gateway Arch on the right (west) side. The Arch is one of the most visually striking landmarks visible from a descending aircraft and is unmistakable from several miles out. Notable sights include: Gateway Arch and St. Louis riverfront, Mississippi River, Missouri River confluence visible to the north, East St. Louis industrial flats across the river.

The flight from Chicago Ohare International (ORD) to Lambert St Louis International (STL) takes Approximately 50-65 minutes.

The flight crosses flat central Illinois agricultural land — large-scale corn and soybean field grids visible as a patchwork of greens and tans. The Illinois River crosses the flight path near Peoria, visible as a meandering dark ribbon. Springfield, Illinois (the state capital) may be visible as a modest urban cluster slightly to the right of track. No significant terrain changes — the entire route sits on the flat Interior Plains, with elevations rarely exceeding 700 feet.