Sit on the Left side of the plane for the best views on flights from Washington to Chicago. The left side delivers the Blue Ridge Mountains on departure and the Chicago skyline with Lake Michigan on approach. Both are the most visually compelling features of this route, and both fall on the left side of the aircraft.

During takeoff from Washington Dulles International (IAD), sit on the Left side for the best views. Dulles typically departs eastbound on runway 1R/19L or westbound on 30. On a westbound departure heading toward Chicago, the left side faces south and picks up the Blue Ridge Mountains and the Shenandoah Valley as the aircraft climbs and turns northwest. The right side faces north toward suburban sprawl with fewer distinctive features. Notable sights include: Blue Ridge Mountains, Shenandoah Valley, Potomac River, Dulles Toll Road corridor.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare predominantly uses runways oriented east-west (9L/27R, 10/28) and north-south (4R/22L). On a typical eastbound arrival from the west or southwest, the left side faces south and gives a clear view of downtown Chicago's skyline, Lake Michigan's shoreline, and the dense urban grid of the city. The right side faces north toward suburban Cook and DuPage counties with less visual interest. Notable sights include: Chicago downtown skyline, Lake Michigan shoreline, Chicago River, suburban grid of the North Shore.

The flight from Washington Dulles International (IAD) to Chicago Ohare International (ORD) takes Approximately 1 hour 45 minutes to 2 hours.

The flight crosses the Allegheny Plateau of western Pennsylvania and eastern Ohio, relatively flat to gently rolling terrain with scattered mid-sized cities including Columbus, Ohio visible below. Indiana farmland dominates the final third before Chicago, with the flat agricultural grid becoming increasingly urban as you approach the metro area.