Sit on the Left side of the plane for the best views on flights from Chicago to Norfolk. While takeoff offers compelling Chicago views, the landing approach into Norfolk provides more sustained and dramatic visual interest with the James River, Hampton Roads, and naval infrastructure. The water features and port activity are more visually distinctive than the relatively flat terrain visible during most of the flight's middle section.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats capture the Chicago skyline and Lake Michigan during the initial climb. Midway typically departs runways 31L/31R or 13L/13R depending on wind; either direction provides good views of the downtown core and the lakefront as you gain altitude over the city. Notable sights include: Chicago downtown skyline (Willis Tower, Trump Tower visible in the cluster), Lake Michigan shoreline, Bridgeport neighborhood industrial areas, Des Plaines River valley.

When landing at Norfolk International (ORF), sit on the Left side for the best views. Left-side seats offer views of the James River, Hampton Roads, and the Norfolk waterfront during descent. Norfolk typically lands on runways 05/23; approach from the north or west provides excellent sightlines of the water features and port infrastructure that define the region. Notable sights include: James River and Hampton Roads waterway, Norfolk Naval Station (visible as distinct pier structures and ship silhouettes), Downtown Norfolk skyline, Eastern Shore barrier islands in the distance.

The flight from Chicago Midway International (MDW) to Norfolk International (ORF) takes Approximately 3 hours 15 minutes.

The flight path crosses the Appalachian foothills (visible as subtle elevation changes and ridge patterns around West Virginia/eastern Kentucky), the Ohio River valley, and transitions into the Atlantic Coastal Plain. The Shenandoah Valley and Blue Ridge Mountains appear as distant ridges on the left (west) side during the middle portion of the flight if departing northeastward. Most of the central flight path crosses relatively flat terrain with scattered clouds typical of the mid-Atlantic region.