Sit on the Left side of the plane for the best views on flights from Chicago to Milano. While takeoff favors the right for Lake Michigan views, the landing approach to MXP from the south/west provides superior scenery: the Alps, Ticino valley, and Lombardy plain are more visually distinctive than Chicago's departure corridor. Left seats capture the best of the transatlantic route's geography.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. MDW typically departs runways 4L/4R or 22L/22R. Right-side seats on eastbound departures (4L/4R) offer views of Lake Michigan's shoreline and the Chicago skyline receding westward. Westbound departures show less dramatic geography initially. Notable sights include: Lake Michigan (immediate eastern boundary), Chicago downtown skyline (west-southwest), Calumet River industrial corridor (south), Indiana dunes region (southeast, distant).

When landing at Malpensa (MXP), sit on the Left side for the best views. Malpensa (MXP) typically uses runways 11L/11R or 35L/35R. Left-side seats on approaches from the south or west offer views of the Alps' southern foothills, the Ticino River valley, and the Lombardy plain. These approaches are more common for transatlantic traffic. Notable sights include: Southern Alps foothills (north, snow-capped in winter), Ticino River valley (west-southwest), Po River plain (south and southeast), Lake Como (northeast, visible on clear days).

The flight from Chicago Midway International (MDW) to Malpensa (MXP) takes Approximately 9.5 to 10.5 hours.

The flight path crosses the Atlantic roughly along 45°N latitude. Notable features include: the North Atlantic (open ocean for ~5 hours), the southern tip of Greenland and Davis Strait region (if routed north), the Irish coast and Celtic Sea (approaching Europe), the United Kingdom and English Channel (if routed south of typical), and finally the European continent including France and Switzerland before descent into northern Italy. The Alps become visible roughly 1.5 hours before landing, initially as a distant ridge on the horizon, then progressively larger as the aircraft descends toward Malpensa.