Sit on the Left side of the plane for the best views on flights from Tokyo to Chicago. Left side delivers the two best moments of the flight: the sweeping view of Tokyo Bay and a possible glimpse of Mount Fuji on departure, and the iconic Chicago skyline with Lake Michigan on approach. The right side offers little of comparable interest at either end of this transpacific routing.

During takeoff from New Tokyo International (NRT), sit on the Left side for the best views. NRT typically departs on runway 16R/34L or 16L/34R. Northbound departures heading toward the Pacific climb out over the Chiba Peninsula and Tokyo Bay. A left-side seat gives you a clear view back over Tokyo Bay, the dense urban grid of central Tokyo, and on clear days Mount Fuji rising to the southwest at roughly 60 miles distance. Notable sights include: Tokyo Bay, central Tokyo urban grid, Mount Fuji (southwest horizon), Chiba Peninsula coastline.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. MDW typically lands on runway 31C or 13C depending on wind. On a runway 31 approach from the southeast, the aircraft tracks over the South Side of Chicago, giving left-side passengers a direct view of the downtown Chicago skyline — the Willis Tower, the lakefront, and Lake Michigan — as the plane descends over the city grid. Right-side passengers see suburban sprawl to the south. Notable sights include: Downtown Chicago skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago South Side street grid, Midway airport runways.

The flight from New Tokyo International (NRT) to Chicago Midway International (MDW) takes Approximately 13 to 14 hours westbound (NRT to MDW), routing northeast over the North Pacific.

The great circle route tracks northeast over the Kuril Islands and Kamchatka Peninsula (volcanic peaks visible on clear days), then across the Gulf of Alaska and the Aleutian Island chain, followed by a long crossing of the open North Pacific. Over Canada the route descends toward the Great Lakes, passing over the boreal forest of Ontario before crossing Lake Michigan into Chicago.