Chicago to Philadelphia is 676 miles (1,088 km), a flight of about 2 hours 10 minutes.
The right side edges out the left thanks to a stronger landing sequence with clear views of Philadelphia's skyline and rivers, plus a better vantage of the Allegheny ridge-and-valley terrain in central Pennsylvania during cruise, which the flight path crosses more directly on that side.
Flight Path
Flat Ohio farmland giving way to the rolling ridges of the Allegheny Plateau, followed by the folded ridge-and-valley terrain of central Pennsylvania and the Susquehanna River valley before the descent toward the Delaware River lowlands.
Great circle distance and headings ›Phase by phase

Takeoff from ORD
LEFTORD eastbound departures often roll on a westward-facing runway before banking south and east to get established on course, giving a brief but clear view of downtown Chicago's skyline and the blue expanse of Lake Michigan off the nose during that turn. The right side only sees flat western suburbs during the same maneuver.

Landing at PHL
RIGHTPHL's typical westward landing runways mean arrivals from the west are vectored around for an eastward final approach, putting Philadelphia's Center City skyline and the Schuylkill River off the right side of the aircraft. The left side mostly shows the flatter South Jersey suburbs and marshland.
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About This Route
Which side of the plane should I sit on flying from Chicago Ohare International (ORD) to Philadelphia International (PHL)?
Sit on the Right side of the plane for the best views on flights from Chicago to Philadelphia. The right side edges out the left thanks to a stronger landing sequence with clear views of Philadelphia's skyline and rivers, plus a better vantage of the Allegheny ridge-and-valley terrain in central Pennsylvania during cruise, which the flight path crosses more directly on that side.
What can I see during takeoff from Chicago Ohare International in Chicago?
During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD eastbound departures often roll on a westward-facing runway before banking south and east to get established on course, giving a brief but clear view of downtown Chicago's skyline and the blue expanse of Lake Michigan off the nose during that turn. The right side only sees flat western suburbs during the same maneuver. Notable sights include: Chicago skyline (Willis Tower, Loop), Lake Michigan shoreline, Chicago's North Side grid.
What can I see when landing at Philadelphia International in Philadelphia?
When landing at Philadelphia International (PHL), sit on the Right side for the best views. PHL's typical westward landing runways mean arrivals from the west are vectored around for an eastward final approach, putting Philadelphia's Center City skyline and the Schuylkill River off the right side of the aircraft. The left side mostly shows the flatter South Jersey suburbs and marshland. Notable sights include: Philadelphia skyline (Comcast Center, City Hall), Schuylkill River, Delaware River bends, PHL runway complex.
How long is the flight from Chicago to Philadelphia?
The flight from Chicago Ohare International (ORD) to Philadelphia International (PHL) takes about 2 hours 10 minutes. The shortest flight path between them is 676 miles (1,088 km); winds and air traffic control usually add a few percent.
What does the Chicago to Philadelphia flight path pass over?
Flat Ohio farmland giving way to the rolling ridges of the Allegheny Plateau, followed by the folded ridge-and-valley terrain of central Pennsylvania and the Susquehanna River valley before the descent toward the Delaware River lowlands.