Sit on the Left side of the plane for the best views on flights from Chicago to Milano. The left seat delivers the standout moment of the flight — the Chicago lakefront and skyline on departure, which is genuinely spectacular. The landing views at Malpensa are better on the right, but the Alpine and lake scenery there is more modest compared to the Chicago skyline panorama. Left wins overall for the departure experience.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare departures heading northeast (the typical routing toward the Atlantic) put Lake Michigan on the left side. You get a clear view of the Chicago lakefront, Grant Park, and the downtown skyline receding as you climb out. The right side faces inland suburban sprawl with little of interest. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Grant Park and Museum Campus, Navy Pier.

When landing at Malpensa (MXP), sit on the Right side for the best views. Malpensa sits northwest of Milan, and aircraft typically approach from the north or west on runways oriented roughly east-west. A right-side seat on approach gives views over Lake Maggiore and the southern Alps foothills, with the Po Valley spreading out ahead. The left side faces more open farmland to the south. Notable sights include: Lake Maggiore (Lago Maggiore), southern Alpine foothills, Po Valley agricultural plain, Ticino River valley.

The flight from Chicago Ohare International (ORD) to Malpensa (MXP) takes Approximately 9 to 9.5 hours.

The route tracks northeast over the Great Lakes (Lake Huron and Lake Erie may be visible on departure), then crosses southern Ontario and Quebec before reaching the Atlantic near Newfoundland. The transatlantic crossing passes south of Greenland and Iceland. Landfall in Europe is typically over Ireland or Scotland, then across England and the North Sea or northern France before descending into the Po Valley. At cruising altitude over the Atlantic there is little to see beyond ocean and occasional cloud cover.