Sit on the Left side of the plane for the best views on flights from Madrid to Chicago. Left side wins both ends of the flight. At takeoff you get the Sierra de Guadarrama and Madrid city. At landing you get the Chicago skyline and Lake Michigan. The mid-Atlantic and Canadian Shield portions of the flight are largely featureless from either side, so the departure and arrival views are what matter most.

During takeoff from Barajas (MAD), sit on the Left side for the best views. Barajas typically departs westbound on runways 32L/32R or eastbound on 18L/18R. On a westbound departure toward the Atlantic, the left side gives you the Sierra de Guadarrama rising sharply to the northwest, with the snow-capped peaks of Peñalara and the Navacerrada pass clearly visible. Madrid city center also sweeps into view to the southwest on the left side. Notable sights include: Sierra de Guadarrama (Peñalara peak), Madrid city grid and Gran Vía corridor, Casa de Campo reservoir, Manzanares River valley.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare predominantly uses runways oriented east-west (9L/9R/10 arrivals from the east, or 27L/27R departures). On a transatlantic arrival typically approaching from the northeast, the left side gives you Lake Michigan's southern shoreline, the Chicago downtown skyline including Willis Tower and the lakefront, and the dense urban grid of the North Side neighborhoods. The right side sees mostly flat suburban sprawl. Notable sights include: Lake Michigan southern shoreline, Chicago downtown skyline (Willis Tower, John Hancock), Chicago River corridor, O'Hare airport layout visible on final.

The flight from Barajas (MAD) to Chicago Ohare International (ORD) takes Approximately 9 to 10 hours.

The flight tracks northwest from Madrid across the Iberian Peninsula, crossing the Cantabrian Mountains and the Bay of Biscay coast near Bilbao or Santander. It then crosses the Atlantic, passing south of Iceland and Greenland. The southern tip of Greenland may be visible on clear days from either side depending on exact routing. The flight crosses Newfoundland and Labrador, where the Canadian Shield's lake-dotted boreal landscape becomes visible, then tracks southwest across Quebec and Ontario before descending into Chicago.