Sit on the Left side of the plane for the best views on flights from Chicago to Tokyo. Left side wins both the departure and arrival phases. During the long polar cruise at 35,000 feet over the North Pacific, neither side has a decisive advantage as views are largely ocean and occasional Aleutian island glimpses, but the left side's superior bookend views at both airports make it the clear overall choice for the journey.

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/10C/10R takes 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 as the plane banks northeast toward the polar route. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Navy Pier, Wrigley Field area in Lincoln Park.

When landing at New Tokyo International (NRT), sit on the Left side for the best views. Flights from Chicago typically approach NRT from the northwest on runway 34L/34R, meaning the aircraft tracks southward on final approach. The left side faces east toward the Pacific coast and Tokyo Bay, giving views of the bay, the urban sprawl of greater Tokyo, and Mount Fuji appearing to the southwest on the right — but the left side captures Tokyo Bay and the Chiba coastline more directly. However, on the more common approach from the northwest descending over Ibaraki Prefecture, the left side faces southwest toward central Tokyo and Tokyo Bay, making it the clear winner. Notable sights include: Tokyo Bay, greater Tokyo urban grid, Chiba industrial waterfront, Narita city and surrounding farmland patchwork.

The flight from Chicago Ohare International (ORD) to New Tokyo International (NRT) takes Approximately 13 to 14 hours westbound.

The great circle route arcs northward over southern Canada and Hudson Bay, then across the Gulf of Alaska and Aleutian Island chain — you may spot individual Aleutian islands such as Unimak or Unalaska as small dark volcanic landmasses in the gray North Pacific below. The route then crosses the Kamchatka Peninsula, where volcanic peaks of the Sredinny Range may be visible through breaks in cloud cover, before descending over the Sea of Okhotsk and Hokkaido, Japan's northernmost main island, before tracking south toward Honshu and Narita.