The right side wins on the strength of a near-guaranteed, tightly clustered view of the National Mall's monuments during climb-out from DCA, a more consistent and iconic scene than the Chicago skyline glimpse on landing, which depends on the runway in use that day.
Flown DCA to MDW? Did we get it right?
Flight Path
Washington to Chicago is 599 miles (964 km), a flight of about 2 hours 10 minutes.
Appalachian ridge-and-valley terrain of western Maryland and Pennsylvania, followed by the rolling farmland of eastern Ohio and the flat plains of Indiana as the route approaches Chicago
Great circle distance and headings ›Phase by phase

Takeoff from DCA
RIGHTDeparting DCA on Runway 01, the initial climb tracks north along the Potomac before banking left toward Chicago, swinging the right side of the aircraft past the National Mall. Passengers get a brief but clear look at the Capitol, Washington Monument, and Jefferson Memorial clustered along the river.

Landing at MDW
LEFTOn approach into Midway, arrivals lined up for runway 13C often swing north of the field before turning onto final, putting downtown Chicago and the Lake Michigan shoreline on the left side of the cabin. It's a brief but recognizable glimpse of the skyline before the turn to land.
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About This Route
Which side of the plane should I sit on flying from Ronald Reagan Washington National (DCA) to Chicago Midway International (MDW)?
Sit on the Right side of the plane for the best views on flights from Washington to Chicago. The right side wins on the strength of a near-guaranteed, tightly clustered view of the National Mall's monuments during climb-out from DCA, a more consistent and iconic scene than the Chicago skyline glimpse on landing, which depends on the runway in use that day.
What can I see during takeoff from Ronald Reagan Washington National in Washington?
During takeoff from Ronald Reagan Washington National (DCA), sit on the Right side for the best views. Departing DCA on Runway 01, the initial climb tracks north along the Potomac before banking left toward Chicago, swinging the right side of the aircraft past the National Mall. Passengers get a brief but clear look at the Capitol, Washington Monument, and Jefferson Memorial clustered along the river. Notable sights include: U.S. Capitol dome, Washington Monument, Jefferson Memorial and Tidal Basin, Potomac River.
What can I see when landing at Chicago Midway International in Chicago?
When landing at Chicago Midway International (MDW), sit on the Left side for the best views. On approach into Midway, arrivals lined up for runway 13C often swing north of the field before turning onto final, putting downtown Chicago and the Lake Michigan shoreline on the left side of the cabin. It's a brief but recognizable glimpse of the skyline before the turn to land. Notable sights include: Chicago skyline (Willis Tower, John Hancock Center), Lake Michigan shoreline, Chicago River mouth, Near South Side neighborhoods.
How long is the flight from Washington to Chicago?
The flight from Ronald Reagan Washington National (DCA) to Chicago Midway International (MDW) takes about 2 hours 10 minutes. The shortest flight path between them is 599 miles (964 km); winds and air traffic control usually add a few percent.
What does the Washington to Chicago flight path pass over?
Appalachian ridge-and-valley terrain of western Maryland and Pennsylvania, followed by the rolling farmland of eastern Ohio and the flat plains of Indiana as the route approaches Chicago