Sit on the Left side of the plane for the best views on flights from Seattle to Chicago. Left side wins both ends of the flight. The Seattle departure offers Elliott Bay and the Olympic Mountains, and the Chicago arrival delivers the best view of the lakefront skyline. During cruise over Montana, Wyoming, and the upper Midwest, the left side also has a slight edge for viewing the Missouri River drainage and the broader northern plains.

During takeoff from Boeing Fld King Co International (BFI), sit on the Left side for the best views. BFI's primary departure runway 13R sends aircraft southeast then turning northeast toward Chicago. A left-side seat captures Elliott Bay, downtown Seattle's skyline, and the Olympic Peninsula across Puget Sound during the initial climb. The right side faces industrial South Seattle and less interesting terrain. Notable sights include: Elliott Bay and downtown Seattle skyline, Puget Sound, Olympic Mountains across the water, Lake Washington to the east.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common arrival runways from the west bring aircraft in from the northwest on headings around 100-110 degrees. A left-side seat on approach looks south over the Chicago metropolitan grid, with Lake Michigan's shoreline and the downtown skyline visible to the southeast. The right side faces suburban sprawl to the north with no comparable landmark. Notable sights include: Chicago downtown skyline along Lake Michigan shoreline, the dense urban street grid of Chicago's North Side, O'Hare's distinctive multi-runway complex visible below, Lake Michigan's western shoreline.

The flight from Boeing Fld King Co International (BFI) to Chicago Ohare International (ORD) takes Approximately 3 hours 45 minutes to 4 hours 15 minutes.

The route crosses the Cascades east of Seattle, then the Columbia Plateau and high desert of eastern Washington and Idaho. Over Montana the terrain flattens into the northern Great Plains. The Missouri River and its tributaries are visible crossing North Dakota and Minnesota. The flight descends over the flat agricultural grid of Wisconsin before entering Illinois airspace.