Sit on the Left side of the plane for the best views on flights from Chicago to Tokyo. The left side wins both takeoff and landing: Lake Michigan and Chicago's shoreline at departure, then Tokyo Bay and the city skyline on arrival into Haneda. The right side offers flat Midwest terrain on departure and a featureless ocean or bay view on approach.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD departures to the north/northwest for a great-circle route to Japan give left-side passengers views over Lake Michigan and the Chicago shoreline before the route curves toward the Great Lakes and Canadian wilderness. The right side just sees flat suburban Chicago sprawl and farmland. Notable sights include: Lake Michigan shoreline, Chicago skyline (distant), O'Hare suburbs, Lake County shoreline.

When landing at Tokyo International (HND), sit on the Left side for the best views. Flights into HND from the north typically curve over Tokyo Bay before landing, and left-side passengers get sweeping views of the Tokyo skyline, the bay's industrial harbors, and Haneda's distinctive over-water runway approach. The right side mostly faces open ocean or featureless bay water during the final descent. Notable sights include: Tokyo Bay, Tokyo skyline including Tokyo Tower area, Rainbow Bridge, Haneda's over-water runway approach.

The flight from Chicago Ohare International (ORD) to Tokyo International (HND) takes 13h 05m.

Great circle route over northern Canada (Hudson Bay region), the Bering Sea, and the Kamchatka Peninsula or Sea of Okhotsk before descending into Japan — almost entirely over remote Arctic terrain and open ocean with no significant visible landmarks from cruising altitude.