Sit on the Right side of the plane for the best views on flights from Chicago to Norfolk. Right-side seats win both segments—Chicago's skyline and Lake Michigan on departure, then Naval Station Norfolk and Hampton Roads on arrival. This is a consistent advantage for the entire flight.

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 22L/22R; either direction gives right-seat passengers a clear view of downtown Chicago's high-rises and the lake's eastern shoreline as you bank northeast or southeast out of the airport. Notable sights include: Chicago downtown skyline (Willis Tower, Trump Tower visible as white points), Lake Michigan shoreline, Bridgeport neighborhood industrial areas to the west, Des Plaines River valley.

When landing at Norfolk Ns (NGU), sit on the Right side for the best views. Right-side seats offer the best views during descent into Norfolk. The approach typically uses runways 05 or 23; either way, right-seat passengers see the Elizabeth River, Naval Station Norfolk (the world's largest naval base), and Hampton Roads waterway with its distinctive shipping channels and naval vessels. The river and base are visually striking from altitude. Notable sights include: Elizabeth River (dark water with visible shipping traffic), Naval Station Norfolk (massive base with visible piers, dry docks, and ship silhouettes), Hampton Roads waterway and bridge-tunnel complex, Willoughby Bay and the James River confluence.

The flight from Chicago Midway International (MDW) to Norfolk Ns (NGU) takes Approximately 2 hours 45 minutes to 3 hours 15 minutes.

The flight path crosses central Ohio and West Virginia at cruise altitude (typically 28,000-32,000 feet). Notable features include the Ohio River valley (visible as a dark sinuous line through forested terrain), the Appalachian plateau with its ridge-and-valley topography becoming more pronounced as you approach Virginia, and the Shenandoah Valley (a long north-south valley visible on clear days). The Appalachian Mountains appear as a series of parallel ridges running northeast-southwest, becoming more defined in the final 45 minutes as you descend toward the Virginia Tidewater region.