Chicago to Portland flight path: MDW to PDX

Sit on the Left side of the plane for the best views on flights from Chicago to Portland. While the Chicago departure offers a brief lake-and-skyline view, the left side wins overall thanks to intermittent views of the northern Rockies and Yellowstone-area high country during cruise, culminating in the dramatic Mount Hood approach into Portland, which the right side lacks.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Departures off Midway toward the southwest or southeast give a brief glimpse of Lake Michigan and the Chicago skyline off to the north before the aircraft turns west over the flat Illinois farmland. This is the only real urban/water interest on the whole route. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline, Midway's grid of suburban neighborhoods.

When landing at Portland International (PDX), sit on the Left side for the best views. On the descent into PDX from the east, the approach path passes just north of Mount Hood, whose snow-capped volcanic cone is clearly visible to the south. This is the single most dramatic landmark on the entire flight, framed against the Cascade foothills and the Columbia River valley. Notable sights include: Mount Hood, Cascade foothills, Columbia River valley, Willamette Valley farmland near Portland.

The flight from Chicago Midway International (MDW) to Portland International (PDX) takes about 4 hours 10 minutes. The shortest flight path between them is 1,747 miles (2,811 km); winds and air traffic control usually add a few percent.

The route crosses the Great Plains of South Dakota, skirts the Black Hills, and traverses the mountainous terrain of Montana and Idaho near the Rocky Mountains before descending toward the Cascade Range and the Columbia River basin.