Sit on the Left side of the plane for the best views on flights from Chicago to Richmond. Left side wins at both ends of the flight. During the cruise portion heading east-southeast, the left side also faces generally north and east, which keeps you oriented toward the Appalachian ridgelines as they come into view over Pennsylvania and Virginia — particularly the parallel ridges of the Ridge and Valley province visible as you descend into Virginia.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common eastbound departures use runways 10L/10R, heading east-southeast. The left (north) side gives you a clear view back over the Chicago metro grid, the lakefront, and downtown's skyline as you bank south. Right side faces suburban sprawl with little of interest. Notable sights include: Chicago downtown skyline and lakefront, Lake Michigan shoreline, Grant Park and Museum Campus area, the dense grid of Chicago's South Side neighborhoods.

When landing at Richmond International (RIC), sit on the Left side for the best views. RIC's primary approach from the west uses runway 34 or runway 02, with aircraft typically descending from the northwest. The left side faces south and east, giving views over the James River, downtown Richmond's skyline, and the river's distinctive bends. Right side looks north into less distinctive suburban terrain. Notable sights include: James River and its broad bends through Richmond, downtown Richmond skyline, Richmond's Fan District street grid, Henrico County suburban sprawl.

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

The flight tracks east-southeast across Indiana and Ohio, then into Pennsylvania and West Virginia. Notable features include the flat agricultural patchwork of Indiana and western Ohio, the Ohio River valley near the Ohio-West Virginia border, and then the most dramatic geography of the flight — the parallel folded ridges of the Appalachian Ridge and Valley province in West Virginia and Virginia, with long linear forested ridges separated by narrow valleys, clearly visible from cruising altitude before descent into Richmond.