Sit on the Left side of the plane for the best views on flights from Chicago to Addis Ababa. Left side wins both ends of the flight. At takeoff you get the full Chicago lakefront panorama, and at landing the Entoto Hills and Addis Ababa's approach are on the left. During the long overwater and Saharan cruise sections there is little to differentiate sides, so the bookend views at departure and arrival are the deciding factor.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common departure heading on runways 10L/10R sends the aircraft eastward, putting the Chicago skyline and Lake Michigan on the left (north) side. You get a clear view of the downtown Loop, Grant Park, and the lakefront stretching toward Evanston before the aircraft turns south. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Navy Pier, Grant Park and Museum Campus.

When landing at Bole International (ADD), sit on the Left side for the best views. Bole International's primary runway 07/25 means arrivals typically come in from the east heading west, or from the west heading east. On the common westward approach (runway 25), the left side faces south toward the Bale Mountains and the Rift Valley escarpment. On an eastward approach (runway 07), the left side faces north toward the Entoto Hills directly above Addis Ababa, which are the most distinctive visual feature near the airport. Notable sights include: Entoto Hills north of Addis Ababa, Ethiopian Rift Valley escarpment to the south, Addis Ababa urban sprawl, Akaki plains.

The flight from Chicago Ohare International (ORD) to Bole International (ADD) takes Approximately 14 to 15 hours nonstop, though most routings connect via European hubs making total travel time 16 to 20 hours.

After departing Chicago the route typically tracks northeast over the Great Lakes and southern Canada, then crosses the North Atlantic toward the UK or Western Europe. Crossing the Mediterranean you may see the Italian or Greek coastlines. The route then passes over Egypt and the Nile Valley — the green ribbon of the Nile Delta and the river corridor through the Eastern Sahara are genuinely visible on clear days. Entering Sudan and Ethiopia the terrain transitions from flat desert to the dramatic Ethiopian Highlands, with deeply dissected plateau terrain and river gorges becoming visible in the final hour of flight.