DCA→MDWWashington to ChicagoRonald Reagan Washington NationaltoChicago Midway International

Sit on the Left side of the plane for the best views on flights from Washington to Chicago. The left side wins both ends of the flight: a monument-filled DC departure and a lakefront Chicago skyline arrival, while the right side offers only flat Midwest farmland with little variety.

During takeoff from Ronald Reagan Washington National (DCA), sit on the Left side for the best views. DCA departures typically head north or west, giving left-side passengers a good look at the Potomac River, the National Mall monuments, and downtown DC skyline before the plane turns toward Chicago. This is one of the most recognizable urban departures in the US. Notable sights include: Potomac River, Washington Monument and National Mall, Capitol dome, Georgetown waterfront.

When landing at Chicago Midway International (MDW), sit on the Left side for the best views. Arrivals into Midway from the east or southeast pass over Lake Michigan's shoreline and give a view of the Chicago skyline before the final approach, including the lakefront and downtown towers. This is a much more visually rewarding approach than the flat suburban terrain to the right. Notable sights include: Lake Michigan shoreline, Chicago skyline (Willis Tower, Sears/Willis area), Navy Pier, Midway's grid-pattern neighborhoods.

The flight from Ronald Reagan Washington National (DCA) to Chicago Midway International (MDW) takes 1h 55m.

The route crosses the rolling Appalachian foothills of western Maryland and Pennsylvania, then the flat agricultural plains of Ohio and Indiana before reaching Lake Michigan near Chicago.