Sit on the Left side of the plane for the best views on flights from Richmond to Chicago. The left side wins at both ends of the flight. Over Richmond you get the James River and city, and over Chicago you get the iconic lakefront and Loop skyline on approach. The left side also tracks closer to the Ohio border and Lake Erie's southern edge during cruise, offering occasional glimpses of agricultural patchwork and river valleys across Indiana and Ohio.

During takeoff from Richmond International (RIC), sit on the Left side for the best views. RIC typically departs on Runway 16 heading southeast or Runway 34 heading northwest. On a northwest departure toward Chicago, the left (south/west) side gives you a clear view back over downtown Richmond and the James River as the aircraft banks northwest. The James River's broad curves and the city grid are distinctly visible during climb-out. Notable sights include: James River curves through Richmond, downtown Richmond skyline, I-95/I-64 interchange sprawl, Henrico County suburban grid.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD arrivals from the southeast typically use runways oriented northeast-southwest. On approach from the southeast, the left side faces north and west, giving a clear view of Lake Michigan's southern shoreline, the Chicago lakefront, and the downtown Loop skyline. The right side faces south over suburban sprawl with far less visual interest. Notable sights include: Lake Michigan southern shoreline, Chicago Loop skyline, Grant Park and Museum Campus peninsula, O'Hare approach over northwest suburban grid.

The flight from Richmond International (RIC) to Chicago Ohare International (ORD) takes Approximately 1 hour 45 minutes to 2 hours.

The flight crosses the Virginia Piedmont, then the Appalachian ridges of the Allegheny Mountains in West Virginia (visible as parallel forested ridgelines), then flattens over the Ohio River valley near Columbus, crossing the broad agricultural plains of central Ohio and Indiana before descending into the Chicago metro. The Wabash and Kankakee river valleys are faintly traceable from altitude.