Sit on the Left side of the plane for the best views on flights from Chicago to Rome. Left side wins at both ends of the flight. During the transatlantic cruise at 35,000 feet over the North Atlantic and then Europe, the left side also faces south, giving occasional views of the British Isles, northern France, and the Alps on the descent into Italy. Right side faces north toward open ocean and northern Europe for most of the cruise.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. Departing ORD, flights typically head east or northeast. A left/south-facing seat gives you a clear view of downtown Chicago's skyline and Lake Michigan's shoreline as you climb out. The grid of Chicago's street layout and Grant Park are clearly visible before you gain altitude. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Grant Park and Museum Campus, Chicago River bends through the Loop.

When landing at Fiumicino (FCO), sit on the Left side for the best views. Fiumicino typically uses runways oriented roughly east-west, with approaches often coming from the northwest or west over the Tyrrhenian Sea. A left seat on approach gives you the best view of Rome's historic center — the Tiber River, the Colosseum area, and the Vatican dome are all to the south and east of the flight path. Right seat faces the Tyrrhenian Sea. Notable sights include: Rome's historic center with Tiber River bends, Vatican City dome of St. Peter's Basilica, Castel Sant'Angelo along the Tiber, Alban Hills (Castelli Romani) to the southeast.

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

The flight path typically arcs northeast over the Great Lakes, then crosses southern Canada and Newfoundland before the North Atlantic crossing. Over Europe it tracks across Ireland or southern England, then over northern France and Germany or Switzerland, with the Alps visible on descent into Italy. The Greenland ice sheet may be visible far to the north on clear days but is not directly overflown on this routing.