Sit on the Left side of the plane for the best views on flights from Portland to Chicago. Left side wins at both ends of the flight. The Mount Hood and Columbia Gorge views on departure are spectacular, and the Chicago skyline with Lake Michigan on approach is the best urban arrival view in the US. The right side offers comparatively little at either airport.

During takeoff from Portland International (PDX), sit on the Left side for the best views. PDX primarily departs eastward on runways 28L/28R (heading roughly 280°) or northward on runway 10L/10R. On a eastbound departure climbing out, the left side faces south and gives you a clear view of Mount Hood dominating the eastern skyline and the Columbia River gorge cutting through the Cascades. The right side faces north toward the less dramatic Washington state lowlands. Notable sights include: Mount Hood (11,249 ft, southeast), Columbia River and its gorge, Mount St. Helens (visible to the north-northwest on clear days), Portland city grid below.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare typically lands from the east or southeast on runways 10L/10R/10C, meaning the aircraft approaches from the west. On this approach, the left side faces south and gives a clear view of downtown Chicago's skyline and Lake Michigan's western shoreline. The right side faces north toward the suburban sprawl with no comparable landmark. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan western shoreline, O'Hare suburban grid, Chicago River corridor.

The flight from Portland International (PDX) to Chicago Ohare International (ORD) takes Approximately 3 hours 30 minutes.

The flight tracks roughly east-southeast across the Snake River Plain in southern Idaho, then over the Rocky Mountain foothills in Wyoming and the high plains of Wyoming and South Dakota, crossing the Missouri River near Sioux City, then descending across the flat agricultural plains of Iowa and northern Illinois. The Rockies are largely behind you within the first hour. No major mountain ranges cross the mid-flight path, but the Snake River Plain and the Missouri River valley are visible on clear days.