Sit on the Left side of the plane for the best views on flights from Madrid to Chicago. While takeoff favors the right for mountain views, the landing experience on the left is more dramatic and sustained—Lake Michigan and Chicago's skyline provide a more memorable finale than Madrid's departure mountains. Left seats win the overall flight.

During takeoff from Barajas (MAD), sit on the Right side for the best views. Right-side seats capture the Sierra de Guadarrama mountain range immediately after departure, which rises prominently north of Madrid. The aircraft typically departs runway 32L or 32R heading northwest, placing these peaks directly off the right wing during the initial climb. Notable sights include: Sierra de Guadarrama (snow-capped in winter, visible ~30 miles north), Manzanares River valley (threading through Madrid's urban sprawl below), Toledo's elevated old town (visible ~40 miles south if climbing slowly), Madrid's northern suburbs and Barajas airport complex itself.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left-side seats offer the best views during approach to Midway. The aircraft typically lands on runway 31L or 31R heading northwest, and left-side passengers see Lake Michigan's shoreline, downtown Chicago's skyline, and the industrial corridor along the Chicago River during the final descent. Notable sights include: Lake Michigan's southern shoreline and harbor areas (dominant water feature), downtown Chicago's Loop district and Willis Tower (visible ~8 miles northeast), Bridgeport neighborhood and industrial areas immediately south of Midway, Chicago River's industrial bend.

The flight from Barajas (MAD) to Chicago Midway International (MDW) takes Approximately 9 hours 15 minutes to 9 hours 45 minutes.

The flight path crosses the Atlantic Ocean for roughly 5-6 hours. Notable geographic features along the route include: the Pyrenees (visible during initial climb if departing northwesterly), the Bay of Biscay (crossed during mid-Atlantic phase), the British Isles and Irish coast (visible on the northern approach to the Atlantic), Greenland's southern tip and Davis Strait (far northern route depending on jet stream), the Canadian Maritime provinces and Great Lakes region (during descent into North America), and the Appalachian Mountains' northern extension visible during final approach to the Midwest.