Sit on the Left side of the plane for the best views on flights from Chicago to Madrid. The left side delivers the more dramatic and iconic urban departure view over Chicago and Lake Michigan, which is genuinely spectacular. The landing view on the right is good but the Sierra de Guadarrama is distant and the approach is over relatively flat terrain. The Chicago departure experience edges it out overall, though switching to the right for landing is worth it if you can grab a window exit row.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common departure heading for eastbound transatlantic flights is runway 10R/10L, heading roughly east. A left (north-facing) seat gives you a clear view back over the Chicago skyline and Lake Michigan shoreline as the aircraft banks right toward the northeast. The downtown Loop, Grant Park, and the lakefront are all distinctly visible on the left side during the climbing turn. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Evanston and North Shore suburbs along the lake.

When landing at Barajas (MAD), sit on the Right side for the best views. Madrid Barajas typically receives transatlantic arrivals from the northwest on runways 32L/32R, meaning the aircraft approaches from the northeast tracking southwest. A right (west-facing) seat gives you a view over the Sierra de Guadarrama mountain range to the northwest of Madrid, with its snow-capped ridgeline clearly visible on descent. The city of Madrid spreads across the right side as you descend through 8,000-10,000 feet. Notable sights include: Sierra de Guadarrama mountain range, Madrid city center and Gran Via corridor, Manzanares River valley, El Pardo forest reserve northwest of the city.

The flight from Chicago Ohare International (ORD) to Barajas (MAD) takes Approximately 8 to 9 hours.

The flight tracks northeast from Chicago over the Great Lakes, crossing Lake Huron and then southern Labrador and Newfoundland. The North Atlantic crossing passes south of Greenland. The European landfall is typically over Ireland or northern Portugal depending on routing, followed by a track across northern Spain over the Cantabrian Mountains and the Castilian Meseta before descending into Madrid.