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 Manhattan's skyline during the climbing bank, and at arrival you face south toward the Chicago lakefront and downtown. The right side sees mostly the open Lake Erie corridor and Indiana farmland with no comparable urban payoff at either end.

During takeoff from La Guardia (LGA), sit on the Left side for the best views. LGA typically departs runway 04 heading northeast, then turns west. The left side gets Manhattan's skyline, the East River, and the Hudson River as the aircraft banks. You're looking directly at Midtown and Lower Manhattan during the climbing turn. Notable sights include: Manhattan skyline (Midtown and Lower), East River and its bridges, Hudson River, Newark and the New Jersey shoreline.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. ORD typically lands on runways 10L/10C/10R from the west, or runway 28 from the east. On the common eastward approach over the western suburbs, the left side faces south toward downtown Chicago and Lake Michigan. The city grid, the lakefront, and the distinctive Chicago skyline are clearly visible on the left during final approach. Notable sights include: Chicago downtown skyline, Lake Michigan shoreline, Chicago River grid, suburban street grid of the western suburbs.

The flight from La Guardia (LGA) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes.

The flight tracks roughly along the 41st parallel west across Pennsylvania, then northern Ohio and Indiana. Notable features include the southern shore of Lake Erie visible to the north over Ohio, the flat agricultural patchwork of Indiana's corn and soybean fields, and the industrial corridor around Gary, Indiana near the Illinois border. No significant terrain — the entire route is essentially flat to gently rolling.