Philadelphia to Chicago is 676 miles (1,088 km), a flight of about 2 hours 5 minutes.
Both sides are modest given the flat Midwest terrain along most of the route, but the right side edges ahead thanks to the Chicago skyline and Lake Michigan shoreline visible during descent into ORD, a more memorable feature than the brief Philadelphia glimpse at departure.
Flight Path
Flat farmland of Pennsylvania, Ohio, and Indiana; the Appalachian Plateau's low rolling hills pass beneath early in the route before the terrain flattens into the Midwest plains.
Great circle distance and headings ›Phase by phase

Takeoff from PHL
LEFTDeparting PHL heading northwest, the left side offers a brief view back over the Philadelphia skyline and the Delaware River before the flight path turns over Pennsylvania farmland. It's a modest but real urban glimpse during initial climb.

Landing at ORD
RIGHTOn approach into ORD from the east, the right side offers views over Lake Michigan's shoreline and the Chicago skyline including the lakefront towers before the final turn inland. This is a well-known scenic approach when runway configuration allows it.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Philadelphia International (PHL) to Chicago Ohare International (ORD)?
Sit on the Right side of the plane for the best views on flights from Philadelphia to Chicago. Both sides are modest given the flat Midwest terrain along most of the route, but the right side edges ahead thanks to the Chicago skyline and Lake Michigan shoreline visible during descent into ORD, a more memorable feature than the brief Philadelphia glimpse at departure.
What can I see during takeoff from Philadelphia International in Philadelphia?
During takeoff from Philadelphia International (PHL), sit on the Left side for the best views. Departing PHL heading northwest, the left side offers a brief view back over the Philadelphia skyline and the Delaware River before the flight path turns over Pennsylvania farmland. It's a modest but real urban glimpse during initial climb. Notable sights include: Philadelphia skyline, Delaware River, Schuylkill River confluence.
What can I see when landing at Chicago Ohare International in Chicago?
When landing at Chicago Ohare International (ORD), sit on the Right side for the best views. On approach into ORD from the east, the right side offers views over Lake Michigan's shoreline and the Chicago skyline including the lakefront towers before the final turn inland. This is a well-known scenic approach when runway configuration allows it. Notable sights include: Chicago skyline, Lake Michigan shoreline, Navy Pier, Willis Tower.
How long is the flight from Philadelphia to Chicago?
The flight from Philadelphia International (PHL) to Chicago Ohare International (ORD) takes about 2 hours 5 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 Philadelphia to Chicago flight path pass over?
Flat farmland of Pennsylvania, Ohio, and Indiana; the Appalachian Plateau's low rolling hills pass beneath early in the route before the terrain flattens into the Midwest plains.