Sit on the Right side of the plane for the best views on flights from Pittsburgh (pennsylva) to Chicago. While the left seat wins at takeoff for Pittsburgh's river confluence, the right seat delivers the more dramatic payoff on approach — Lake Michigan and the Chicago skyline together on final into O'Hare is one of the better urban approach views in the Midwest. The right side also tracks the southern shore of Lake Erie at cruise altitude during the middle portion of the flight.

During takeoff from Pittsburgh International (PIT), sit on the Left side for the best views. Departing PIT typically uses runways oriented toward the west or northwest. A left-side seat gives you a clear view back over downtown Pittsburgh, the confluence of the three rivers (Allegheny, Monongahela, and Ohio), and the city's distinctive triangular Point State Park. The urban grid and river valleys are unmistakable from climb-out. Notable sights include: Point State Park and the three rivers confluence, downtown Pittsburgh skyline, the Ohio River valley heading west, Pittsburgh's South Side hills and bridges.

When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. Arriving at O'Hare from the east, aircraft typically approach on westerly headings using runways 10/28 or 9R/27L. A right-side seat on approach gives you a view south over the Chicago lakefront, Grant Park, and the Loop skyline as you descend over the northern suburbs. Lake Michigan fills the right window with the city's iconic waterfront clearly visible. Notable sights include: Lake Michigan shoreline, Chicago Loop skyline and Willis Tower, Grant Park and Museum Campus, O'Hare's distinctive runway complex.

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

The flight tracks northwest across Ohio at cruise altitude, passing over or near Cleveland and the southern shore of Lake Erie. The flat agricultural patchwork of northern Ohio and Indiana is visible below. Lake Erie's southern coastline may be visible to the right (north) side depending on exact routing. As you cross into Illinois, the landscape flattens further into the Illinois prairie before the Chicago metro sprawl becomes visible on descent.