Sit on the Left side of the plane for the best views on flights from Milano to Chicago. The takeoff experience over the Alps is more visually dramatic and geographically distinctive than the landing approach. While the landing offers urban and water features, the Alpine scenery during departure is more striking and memorable for most passengers.

During takeoff from Malpensa (MXP), sit on the Left side for the best views. Left side offers views of the Alps immediately after departure from Malpensa. The aircraft climbs northwestward initially, positioning left-side passengers to see the snow-capped peaks of the Monte Rosa massif and surrounding ranges as they recede beneath the climb. Notable sights include: Alps (Monte Rosa, Gran Paradiso ranges), Lake Maggiore, Ticino River valley, Po River plain.

When landing at Chicago Midway International (MDW), sit on the Right side for the best views. Right side provides views during the descent approach into Chicago Midway. The aircraft descends from the northeast, and right-side passengers see Lake Michigan's shoreline, downtown Chicago's skyline, and the urban sprawl of the South Side as the airport lies southwest of the city center. Notable sights include: Lake Michigan, Chicago downtown skyline, Illinois prairie, Des Plaines River.

The flight from Malpensa (MXP) to Chicago Midway International (MDW) takes 9h 15m.

The flight path crosses the Atlantic Ocean for approximately 5-6 hours with no significant visible landmarks. Over the ocean, passengers may see the Greenland ice sheet's eastern edge if the northern routing is used, or open Atlantic water if the more typical southern routing is flown. Upon approaching North America, the Canadian Maritime provinces (Nova Scotia, Newfoundland) appear as rocky, forested coastlines. The flight then crosses the Canadian interior and Great Lakes region, where Lake Superior, Lake Michigan, and the transition from boreal forest to agricultural Midwest become visible during descent into Chicago.