Sit on the Left side of the plane for the best views on flights from New York to Chicago. Left side wins both ends of the flight. At departure you get the full Manhattan panorama over Jamaica Bay, and on arrival you get the Chicago lakefront and Loop skyline. The mid-flight portion over Pennsylvania and Indiana is relatively flat and unremarkable, so the terminal views are what matter most on this route.

During takeoff from John F Kennedy International (JFK), sit on the Left side for the best views. JFK's most common departure is runway 31L/31R heading northwest, which puts Manhattan directly on the left side as you climb out over Jamaica Bay. You get a clear view of the entire skyline, the Hudson River, and the bridges connecting the boroughs. Notable sights include: Manhattan skyline, Jamaica Bay, Verrazano-Narrows Bridge, Hudson River.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common arrival from the east uses runways 10L/10R or 9L/9R, approaching from the east-northeast. The left side gives you a view south over the Chicago lakefront, Grant Park, and the Loop skyline as you descend, with Lake Michigan stretching to the horizon. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park, Wrigley Field area.

The flight from John F Kennedy International (JFK) to Chicago Ohare International (ORD) takes Approximately 2 hours 30 minutes.

The flight tracks roughly along the 41st parallel, passing over the Pocono Mountains in northeastern Pennsylvania (modest forested ridges visible), then the flat agricultural plains of central Pennsylvania and Ohio, the southern shore of Lake Erie may be faintly visible to the north over Ohio, followed by the flat Indiana farmland grid before the Chicago suburbs appear on descent.