Sit on the Right side of the plane for the best views on flights from Tokyo to Chicago. The right side wins overall because the Haneda departure delivers the spectacular Tokyo cityscape and Mount Fuji view, which is one of the most dramatic urban departure views in aviation. The landing advantage on the left is real but the Chicago approach view, while excellent, is more commonly seen. If you can only pick one side for the whole flight, right side gives you the better departure spectacle.

During takeoff from Tokyo International (HND), sit on the Right side for the best views. HND typically departs northward or eastward over Tokyo Bay on runways 34L/34R or 05. A right-side seat gives you the Tokyo city skyline, the dense urban grid of central Tokyo, and a clear view back toward the bay as you climb out. Left side faces the bay water with less visual interest. Notable sights include: Tokyo Bay, central Tokyo urban grid and Shinjuku skyscraper cluster, Rainbow Bridge and Odaiba waterfront, Mount Fuji visible to the southwest as you gain altitude.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. MDW sits on Chicago's southwest side, and aircraft typically approach from the east or northeast on runways 31C/31L or from the south. A left-side seat on approach gives you Lake Michigan's shoreline, the downtown Chicago skyline including the Willis Tower cluster, and Grant Park laid out clearly below. Right side faces inland suburban sprawl. Notable sights include: Lake Michigan shoreline and lakefront, Chicago downtown skyline with Willis Tower, Grant Park and Museum Campus, the dense street grid of Chicago's South Side.

The flight from Tokyo International (HND) to Chicago Midway International (MDW) takes Approximately 12 to 13 hours westbound across the North Pacific.

The great circle route arcs northeast over the North Pacific, passing south of the Aleutian Islands chain, crossing the Gulf of Alaska, and then over the Canadian Rockies in British Columbia and Alberta before descending over the Great Plains of the American Midwest. The Aleutian Islands appear as a scattered volcanic chain on the northern horizon mid-flight, and the snow-covered Canadian Rockies are visible during descent if flying in daylight. The vast featureless North Pacific occupies the majority of the flight.