Sit on the Left side of the plane for the best views on flights from Chicago to Taipei. The left side wins overall. The Chicago departure view is the most dramatic moment of the flight — the skyline and Lake Michigan together make for a genuinely spectacular climb-out. Over the Pacific the views are largely ocean on both sides, and the Taipei arrival advantage on the right is real but more subtle. The Chicago departure spectacle tips the balance to the left.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's dominant departure runways (9L/9R heading east, or 10L/10R) put the left side facing north toward the Chicago skyline and Lake Michigan's southern shoreline. As the aircraft climbs and turns northeast toward the Pacific routing, the left side gets a clear view of downtown Chicago's dense tower cluster and the lake stretching to the horizon. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan southern basin, Chicago River corridor, suburban grid of the North Shore.

When landing at Chiang Kai Shek International (TPE), sit on the Right side for the best views. Taoyuan International typically uses runways 05L/05R or 23L/23R. On the common approach from the north over the Taiwan Strait, aircraft descend from the northwest, putting the right side facing south and east toward the Taipei Basin, the Xueshan Range foothills, and the urban sprawl of Taoyuan and Taipei. The left side faces mostly open Taiwan Strait water. Notable sights include: Taipei Basin urban area, Xueshan Mountain Range foothills to the east, Taoyuan urban grid, Taiwan Strait coastline.

The flight from Chicago Ohare International (ORD) to Chiang Kai Shek International (TPE) takes Approximately 15 to 16 hours nonstop.

The great circle route from Chicago to Taipei tracks northeast over Lake Michigan, then across southern Ontario and Quebec, then over Labrador and the Labrador Sea, arcing over southern Greenland or just south of it, then across the North Pacific — passing south of the Aleutian Islands chain, over the open North Pacific Ocean, before descending toward Japan's Ryukyu Islands and then the Taiwan Strait. The route passes near Hokkaido and the Japanese archipelago in the final hours, where the Japanese coastline and possibly Mount Fuji may be distantly visible depending on exact routing and conditions.