Sit on the Right side of the plane for the best views on flights from Chicago to Philadelphia. The right side delivers the more dramatic single moment — the Chicago skyline and Lake Michigan on departure are genuinely spectacular and hard to beat. The left side has a good Philadelphia approach view, but the Chicago departure on the right is the highlight of this route.

During takeoff from Chicago Ohare International (ORD), sit on the Right side for the best views. O'Hare's most common eastbound departures use runways 10R/10L, heading east-southeast. From the right side you get a clear view of downtown Chicago's skyline and the lakefront as the aircraft climbs and turns. Lake Michigan fills the window with the city grid stretching south along the shore. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Grant Park and Museum Campus, Chicago River grid.

When landing at Philadelphia International (PHL), sit on the Left side for the best views. PHL's primary eastbound arrivals typically use runways 27L/27R, meaning the aircraft approaches from the east heading west. On the left side you get views of the Delaware River, the Philadelphia skyline, and South Jersey wetlands on approach. The city sits to the north of the flight path on final. Notable sights include: Philadelphia downtown skyline, Delaware River, South Jersey Pine Barrens and wetlands, Delaware Bay in the distance on approach.

The flight from Chicago Ohare International (ORD) to Philadelphia International (PHL) takes Approximately 2 hours to 2 hours 15 minutes.

The flight tracks east-southeast across northern Indiana, then over Ohio — largely flat agricultural land with the Ohio River valley visible in southern Ohio. Crossing into Pennsylvania the terrain rises into the Allegheny Plateau and the Ridge and Valley region of the Appalachians, with parallel forested ridgelines visible below. The Susquehanna River is a notable feature crossing Pennsylvania before descending toward Philadelphia.