Sit on the Right side of the plane for the best views on flights from Chicago to Pittsburgh (pennsylva). The right side delivers the most dramatic single moment of the flight — the Chicago skyline and Lake Michigan shoreline on departure. The landing view from the left is excellent but Pittsburgh's geography is best appreciated from slightly higher altitude. If you can only pick one side for the whole flight, right gives you the Chicago payoff at takeoff and still reasonable views of Pennsylvania's river valleys on descent.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. ORD's most common eastbound departures use runways 10R/10L heading east-southeast. From the right side you get a clear view south over downtown Chicago's skyline and Lake Michigan's shoreline curving away. The left side faces north toward suburban sprawl with no comparable landmark density. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Indiana Dunes coastline, Chicago River corridor.

When landing at Pittsburgh International (PIT), sit on the Left side for the best views. Pittsburgh International sits west of the city, and aircraft typically approach from the west on runway 28R/28L or from the east on 10R. On a standard ILS approach from the west heading east, the left side faces north and picks up the Ohio River valley and the city of Pittsburgh's downtown triangle where the Allegheny and Monongahela rivers meet. The right side faces south toward less distinctive terrain. Notable sights include: Pittsburgh downtown Golden Triangle (confluence of Allegheny and Monongahela rivers), Ohio River valley, Monongahela River corridor, Allegheny River.

The flight from Chicago Ohare International (ORD) to Pittsburgh International (PIT) takes Approximately 1 hour to 1 hour 15 minutes.

The flight crosses northern Indiana's flat agricultural plains, then enters Ohio passing near Toledo and Cleveland's general latitude before cutting into western Pennsylvania. The terrain transitions from Midwest flatlands to the rolling Allegheny Plateau with increasing forest cover and river valleys. No major mountain ranges are crossed — the Alleghenies proper are largely south of this flight path.