Sit on the Right side of the plane for the best views on flights from Chicago to New York. The right side delivers the dramatic Chicago lakefront departure, and while the Manhattan view on landing favors the left, the right side still gets decent views of Long Island and the Atlantic coast on descent. The Chicago departure spectacle on the right is the highlight of this route and tips the balance.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. ORD departures heading east on runways 10R/10L put the Chicago skyline and Lake Michigan on the right side. You get a clear view of the downtown Loop, the lakefront, and the southern shore of Lake Michigan as the aircraft climbs out eastward. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Grant Park and Museum Campus, Indiana Dunes coastline.

When landing at John F Kennedy International (JFK), sit on the Left side for the best views. JFK arrivals from the west typically use runways 31L/31R or 22L/22R. On the 31 heading (northwest approach), the left side gives you Manhattan's skyline, the Hudson River, and the Verrazano-Narrows Bridge as you descend over Jamaica Bay. On the 22 heading, the left side still captures the southern Brooklyn coastline and the Atlantic approach. Notable sights include: Manhattan skyline, Verrazano-Narrows Bridge, Jamaica Bay, Long Island coastline.

The flight from Chicago Ohare International (ORD) to John F Kennedy International (JFK) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight tracks roughly east-northeast across northern Indiana, then over northern Ohio near Toledo and Lake Erie's southern shore, then across northern Pennsylvania's Allegheny Plateau — largely forested rolling terrain — before descending over the Hudson Valley and into the New York metro area. Lake Erie is briefly visible from the right side over northern Ohio. The Allegheny and Pocono highlands are visible as dark forested ridges below during cruise.