Chicago to Richmond is 641 miles (1,032 km), a flight of about 1 hour 45 minutes.
The right side wins overall thanks to the James River and Piedmont foothill views during the Richmond approach, since the takeoff and cruise phases over the Midwest and Appalachian foothills are largely flat and unremarkable on both sides.
Flight Path
Flat Indiana and Ohio farmland giving way to the low, forested ridges of the Allegheny Plateau in West Virginia before descending toward Virginia's Piedmont region and the James River.
Great circle distance and headings ›Phase by phase

Takeoff from ORD
LEFTEastbound departures from ORD give a brief glimpse of Chicago's southern suburbs and, on clear days, a sliver of Lake Michigan's shoreline off to the north before the aircraft turns onto its southeast heading over flat Illinois farmland.
Landing at RIC
RIGHTApproaching RIC from the northwest, the right side offers views of the rolling Piedmont foothills and the James River as it winds through Richmond before the final turn onto runway 16, giving more terrain variety than the flatter coastal-plain side.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Chicago Ohare International (ORD) to Richmond International (RIC)?
Sit on the Right side of the plane for the best views on flights from Chicago to Richmond. The right side wins overall thanks to the James River and Piedmont foothill views during the Richmond approach, since the takeoff and cruise phases over the Midwest and Appalachian foothills are largely flat and unremarkable on both sides.
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. Eastbound departures from ORD give a brief glimpse of Chicago's southern suburbs and, on clear days, a sliver of Lake Michigan's shoreline off to the north before the aircraft turns onto its southeast heading over flat Illinois farmland. Notable sights include: Chicago southern suburbs, Lake Michigan shoreline (distant), grid-pattern Illinois farmland.
What can I see when landing at Richmond International in Richmond?
When landing at Richmond International (RIC), sit on the Right side for the best views. Approaching RIC from the northwest, the right side offers views of the rolling Piedmont foothills and the James River as it winds through Richmond before the final turn onto runway 16, giving more terrain variety than the flatter coastal-plain side. Notable sights include: James River, Richmond downtown skyline, Piedmont foothills, forested river bluffs.
How long is the flight from Chicago to Richmond?
The flight from Chicago Ohare International (ORD) to Richmond International (RIC) takes about 1 hour 45 minutes. The shortest flight path between them is 641 miles (1,032 km); winds and air traffic control usually add a few percent.
What does the Chicago to Richmond flight path pass over?
Flat Indiana and Ohio farmland giving way to the low, forested ridges of the Allegheny Plateau in West Virginia before descending toward Virginia's Piedmont region and the James River.