Sit on the Left side of the plane for the best views on flights from Chicago to Portland. The left side wins at both ends of the flight. During the cruise over the northern Rockies and Cascades, the left side also tends to face slightly more southward, giving better angles on the volcanic peaks of the Cascades as you approach Oregon. Right side has merit over the Columbia River on descent but left is stronger overall.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD departures heading west or northwest on runways 10/28 or 9L/27R give the left side a clear view back over downtown Chicago and Lake Michigan. As the aircraft banks northwest, the left side tracks the lakefront, the Loop skyline, and the southern shore of Lake Michigan stretching toward Indiana. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Wrigley Field neighborhood (Lakeview), O'Hare's own runway complex below.

When landing at Portland International (PDX), sit on the Left side for the best views. PDX sits on the east bank of the Willamette River, and aircraft typically land on runways 28L/28R heading west. On approach from the east, the left side faces south and gives a sustained view of Mount Hood dominating the eastern horizon, the Columbia River Gorge, and the Willamette Valley spreading out below. The right side faces north toward the Columbia River but misses the volcanic peaks. Notable sights include: Mount Hood (11,249 ft), Columbia River Gorge, Willamette River, Portland city grid west of the airport.

The flight from Chicago Ohare International (ORD) to Portland International (PDX) takes Approximately 4 hours 15 minutes to 4 hours 45 minutes.

The flight tracks northwest over Wisconsin and Minnesota, then crosses the northern Great Plains of North Dakota and Montana. Over Montana the Rocky Mountain Front becomes visible — the Lewis Range and Glacier National Park area. Crossing into Idaho, the Bitterroot Range and Clearwater Mountains appear. As the flight enters Oregon, the Blue Mountains cross below before the descent toward the Columbia Plateau and the Cascades. On clear days, Mount Rainier, Mount Adams, and Mount Hood are all visible in sequence as the aircraft approaches Portland from the east.