Sit on the Right side of the plane for the best views on flights from Seattle to Chicago. Right-side seats win overall because the takeoff view of Mount Rainier and the Cascades is more visually distinctive and memorable than the landing approach. While the landing offers good Lake Michigan views, the dramatic volcanic peak and mountain range during departure provide a superior window experience.

During takeoff from Boeing Fld King Co International (BFI), sit on the Right side for the best views. Right-side seats capture the Cascade Range immediately after departure. BFI typically departs to the east or northeast, and right-side windows frame Mount Rainier and the Cascade peaks as they rise dramatically from the Puget Sound lowlands during climb-out. Notable sights include: Mount Rainier (14,410 ft, ~60 miles southeast), Cascade Range spine, Puget Sound shoreline, Lake Washington.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Left-side seats provide the best view during approach to Midway. Aircraft typically descend from the northeast and enter the landing pattern over Lake Michigan, and left-side windows frame the lake's expanse, downtown Chicago's skyline, and the transition from water to urban landscape. Notable sights include: Lake Michigan (massive freshwater body), Chicago downtown skyline and Willis Tower, Lake Shore Drive corridor, industrial areas south of downtown.

The flight from Boeing Fld King Co International (BFI) to Chicago Midway International (MDW) takes Approximately 4 hours 45 minutes to 5 hours 15 minutes.

The flight path crosses the Columbia River basin and enters the High Plains. Notable features include the Cascade Range (visible during departure), the Blue Mountains of Oregon, the Snake River Plain, the Wallowa Mountains, and eventually the transition into the Great Plains of Montana and Wyoming. The Rocky Mountains remain south of the typical flight corridor at cruise altitude. The flight crosses into airspace over the Great Plains, with increasingly flat terrain as it approaches the Mississippi River valley and Illinois.