Sit on the Left side of the plane for the best views on flights from Washington to Chicago. Left side wins both ends of the flight — the DC monuments on departure and the Chicago skyline with Lake Michigan on approach. The left side also tracks closer to the southern shore of Lake Erie in the mid-flight portion, offering occasional glimpses of water on clear days.

During takeoff from Ronald Reagan Washington National (DCA), sit on the Left side for the best views. DCA's primary northbound departure on Runway 1 takes you over the Potomac River immediately after liftoff, with the left side giving you a direct view of the National Mall, Capitol Hill, and the monuments. The flight path curves northwest, keeping DC's core on your left through the climb. Notable sights include: National Mall and Lincoln Memorial, Washington Monument, Capitol Building, Potomac River.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals from the east typically use runways oriented east-west, with the approach over the western suburbs giving left-side passengers a view of Lake Michigan on the horizon and the Chicago skyline to the southeast. The dense grid of Chicago's north and northwest sides is clearly visible on the left during descent. Notable sights include: Lake Michigan shoreline, Chicago downtown skyline, O'Hare airport complex, Illinois suburban grid.

The flight from Ronald Reagan Washington National (DCA) to Chicago Ohare International (ORD) takes Approximately 1 hour 45 minutes to 2 hours.

The flight crosses the Allegheny Plateau in western Pennsylvania, then flattens into the Ohio agricultural plain. The southern tip of Lake Erie may be visible on clear days near the Ohio-Pennsylvania border. Indianapolis and its suburban sprawl are sometimes visible to the south. The terrain is predominantly flat farmland from Ohio westward into Indiana and Illinois, with the Chicago metro area expanding visibly on approach.