Sit on the Left side of the plane for the best views on flights from Newark to Chicago. The left side delivers the best views at both ends of the flight — Manhattan and New York Harbor on departure, and the Chicago lakefront and Loop on approach. The flight path runs nearly due west, so neither side has a dramatic advantage mid-flight, but the left side wins on the landmark bookends.

During takeoff from Newark Liberty International (EWR), sit on the Left side for the best views. EWR typically departs westbound or northbound on runways 22L/22R or 04L/04R. On a westbound departure, the left side gives you the Manhattan skyline and Upper New York Bay before the aircraft turns toward Pennsylvania. The Hudson River and Newark Bay are clearly visible below during climb-out. Notable sights include: Manhattan skyline, Upper New York Bay, Newark Bay, Hudson River.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD most commonly lands on runways 10L/10R or 28L/28R. On an easterly approach over Lake Michigan, the left side gives you the Chicago lakefront, Grant Park, and the downtown Loop skyline as the aircraft descends over the southern suburbs. The lake's blue expanse and the city grid are clearly laid out below. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park, suburban street grid of Cook County.

The flight from Newark Liberty International (EWR) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight crosses northern New Jersey, then Pennsylvania's rolling Appalachian ridges (Pocono Plateau and Allegheny Front visible as parallel forested ridgelines), then the flat agricultural patchwork of northern Ohio and Indiana. Lake Erie may be briefly visible to the north over Ohio. The terrain flattens dramatically west of the Appalachians into the corn and soybean grid of the Midwest, with small towns and river corridors visible below.