Richmond to Chicago is 641 miles (1,032 km), a flight of about 1 hour 50 minutes.
The left side wins overall because the mountainous terrain of the Blue Ridge and Alleghenies during climb-out offers sustained, dramatic scenery, while the right side's payoff is a shorter skyline view only during the final approach minutes.
Flight Path
Appalachian ridgelines of West Virginia give way to the Ohio River valley, followed by the flat farmland of Ohio, Indiana, and Illinois as the route levels out toward Chicago.
Great circle distance and headings ›Phase by phase
Takeoff from RIC
LEFTClimbing out from RIC on a northwesterly track toward Chicago, the left side faces south across the Blue Ridge Mountains and Shenandoah Valley as the terrain rises into the Alleghenies. This gives a much more textured view than the flat farmland that dominates the right side of the climb.

Landing at ORD
RIGHTOn approach to ORD from the east, arrivals commonly track north past the city before turning to land on the east-west runways, putting Chicago's skyline and the Lake Michigan shoreline on the right side of the aircraft. The left side during this phase only shows flat suburban Illinois farmland.
Landmarks on this routeAll landmarks →
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About This Route
Which side of the plane should I sit on flying from Richmond International (RIC) to Chicago Ohare International (ORD)?
Sit on the Left side of the plane for the best views on flights from Richmond to Chicago. The left side wins overall because the mountainous terrain of the Blue Ridge and Alleghenies during climb-out offers sustained, dramatic scenery, while the right side's payoff is a shorter skyline view only during the final approach minutes.
What can I see during takeoff from Richmond International in Richmond?
During takeoff from Richmond International (RIC), sit on the Left side for the best views. Climbing out from RIC on a northwesterly track toward Chicago, the left side faces south across the Blue Ridge Mountains and Shenandoah Valley as the terrain rises into the Alleghenies. This gives a much more textured view than the flat farmland that dominates the right side of the climb. Notable sights include: Blue Ridge Mountains, Shenandoah Valley, Allegheny Highlands, James River near Richmond.
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 to ORD from the east, arrivals commonly track north past the city before turning to land on the east-west runways, putting Chicago's skyline and the Lake Michigan shoreline on the right side of the aircraft. The left side during this phase only shows flat suburban Illinois farmland. Notable sights include: Chicago skyline (Willis Tower, Loop skyscrapers), Lake Michigan shoreline, Navy Pier, O'Hare's surrounding grid of suburbs.
How long is the flight from Richmond to Chicago?
The flight from Richmond International (RIC) to Chicago Ohare International (ORD) takes about 1 hour 50 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 Richmond to Chicago flight path pass over?
Appalachian ridgelines of West Virginia give way to the Ohio River valley, followed by the flat farmland of Ohio, Indiana, and Illinois as the route levels out toward Chicago.