Sit on the Right side of the plane for the best views on flights from Chicago to Rome. While left offers good Chicago departure views, right wins overall because the transatlantic crossing provides extended views of the Atlantic, and the descent into Rome with the Apennines and Tiber valley is more visually dramatic and geographically distinctive than the departure.

During takeoff from Chicago Midway International (MDW), sit on the Left side for the best views. Left side offers views of Lake Michigan immediately after departure, with the Chicago skyline visible to the north. The aircraft climbs northeastward over the lake, providing clear water and urban contrast. Notable sights include: Lake Michigan, Chicago downtown skyline, Indiana shoreline to the south, suburban sprawl extending inland.

When landing at Fiumicino (FCO), sit on the Right side for the best views. Right side provides views of the Apennine Mountains as the aircraft descends into Rome from the northeast. The mountains form a dramatic backdrop to the Tiber River valley and the city itself during final approach. Notable sights include: Apennine Mountains, Tiber River valley, Roman Campagna (agricultural plains), city of Rome sprawling across low hills.

The flight from Chicago Midway International (MDW) to Fiumicino (FCO) takes Approximately 9 to 9.5 hours.

The flight path crosses the North Atlantic, typically passing south of Greenland and Iceland. Over the Atlantic, you may see the Mid-Atlantic ridge features and deep ocean color variations. Approaching Europe, the flight passes over the British Isles and France—the English Channel, the Seine River valley, and the Loire River valley are visible on clear days. The Alps appear as a major mountain range on the right side during the approach to Italy, with Mont Blanc visible as a prominent peak. The flight then descends over the Po River valley in northern Italy before turning south toward Rome.