Portland to Chicago flight path: PDX to MDW

Sit on the Right side of the plane for the best views on flights from Portland to Chicago. The right side wins overall because the PDX departure delivers a genuinely dramatic, close-up view of Mt. Hood, a rare treat among US domestic departures, while the cruise and landing phases are relatively flat and comparable on both sides.

During takeoff from Portland International (PDX), sit on the Right side for the best views. Departing PDX to the east, the flight path runs along the Columbia River corridor, and the right side offers a close, dramatic view of Mt. Hood's snow-capped cone rising above the Cascade foothills. This is one of the most recognizable volcanic peaks visible from any US airport departure. Notable sights include: Mt. Hood, Columbia River, Cascade foothills, Sandy River valley.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. On approach into Midway from the southwest, the final turn brings the Chicago skyline into view off the left side, with downtown's skyscrapers and the Lake Michigan shoreline visible before the plane lines up with the runway over the dense southwest side neighborhoods. Notable sights include: Chicago skyline, Willis Tower, Lake Michigan shoreline, Midway's dense grid of residential streets.

The flight from Portland International (PDX) to Chicago Midway International (MDW) 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.

Snake River Plain and Rocky Mountain foothills of Idaho, high plains of Wyoming and Nebraska, and the Missouri River valley as the route crosses into the Midwest