Sit on the Left side of the plane for the best views on flights from Milano to Chicago. Left side wins both ends of the flight. At departure you get the Alps and Lake Maggiore; at arrival you get the Chicago skyline and Lake Michigan. Over the Atlantic the left side also faces south toward Greenland's ice sheet and the Canadian coastline as the great circle route arcs northward.

During takeoff from Malpensa (MXP), sit on the Left side for the best views. Malpensa typically departs on runway 35L/35R heading north, then turns westbound toward the Atlantic. A left (west/south-facing) seat gives you the Alps as you climb out — the full arc from Monte Rosa to the Matterhorn is visible on a clear day. The Po Valley spreads out below before you gain altitude. Notable sights include: Monte Rosa massif to the southwest, Lake Maggiore directly below during climb-out, the Po Valley flatlands stretching south, and the snow-capped Alpine ridge toward the Matterhorn on the horizon.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare most commonly lands on runways oriented east-west (9L/9R or 10L/10R from the west, or 27L/27R from the east). On a transatlantic arrival from the northeast, aircraft typically approach from the east or southeast, giving left-side passengers a view over downtown Chicago and Lake Michigan. The Chicago skyline and the lakefront are unmistakable on approach. Notable sights include: Downtown Chicago skyline (Willis Tower, John Hancock) visible to the southeast, Lake Michigan's western shoreline, the Chicago River corridor, and the dense urban grid of the North Side neighborhoods.

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

The great circle route from MXP to ORD passes over the Swiss and French Alps shortly after departure, then crosses southern England or northern France, exits over Ireland or southwestern UK, arcs north over the North Atlantic passing south of Iceland, crosses southern Greenland or the Labrador Sea, enters Canadian airspace over Newfoundland or Quebec, then tracks southwest over Ontario and the Great Lakes before descending into Chicago. Greenland's ice cap and the St. Lawrence River valley are the most visually dramatic midpoint features.