Sit on the Left side of the plane for the best views on flights from Seattle to Chicago. The left side delivers the most dramatic single moment of the flight — Mount Rainier and the Cascades on departure — plus decent views of the northern Rockies and Montana plains en route. The right side at landing is strong for Chicago, but the Cascades sequence at takeoff is the visual highlight of the whole trip.

During takeoff from Seattle Tacoma International (SEA), sit on the Left side for the best views. SEA primarily uses runways 16L/16R for southbound departures, meaning a left-side seat faces east toward the Cascade Range. You get a clear view of Mount Rainier dominating the skyline, with the Seattle city skyline and Elliott Bay visible during the initial climb before the turn eastward. Notable sights include: Mount Rainier, Elliott Bay and Seattle waterfront, Lake Washington, Cascade Range foothills.

When landing at Chicago Midway International (MDW), sit on the Right side for the best views. Midway typically uses runways 31C/31L for northwest arrivals, meaning the approach comes from the southeast over Indiana. A right-side seat faces north and gives you the Chicago lakefront, Grant Park, the Loop skyline, and Lake Michigan as you descend over the south suburbs. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Calumet industrial waterway.

The flight from Seattle Tacoma International (SEA) to Chicago Midway International (MDW) takes Approximately 3 hours 30 minutes to 3 hours 50 minutes.

After crossing the Cascades, the route tracks over the Columbia Basin and then the northern Rocky Mountain ranges of Idaho and Montana, including the Bitterroot Range and Glacier-area peaks visible to the north. Over North Dakota and Minnesota the terrain flattens into the Great Plains and then the Upper Midwest agricultural grid, with the Mississippi River crossing near the Wisconsin-Minnesota border visible as a wide, winding dark ribbon cutting through the flat farmland.