Sit on the Left side of the plane for the best views on flights from Rapid City to Chicago. Left side wins both ends of the flight. During the cruise over South Dakota, Minnesota, and Wisconsin, the left side also gives slightly better angles on the Mississippi River crossing near the Wisconsin-Minnesota border and the broader river valley system. It is the clear choice for the full journey.

During takeoff from Ellsworth Afb (RCA), sit on the Left side for the best views. Ellsworth AFB runways are oriented roughly east-west. Departing eastbound toward Chicago, the left (north) side gives you a clear look back at the Black Hills massif and Harney Peak area as you climb out. The right side faces south toward open plains with little of interest. Notable sights include: Black Hills uplift to the northwest, Harney Peak (Black Elk Peak) visible as the highest point in the range, Rapid City urban grid below, Badlands escarpment edge to the east-southeast.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare arrivals from the west typically use runways oriented east-west or on a slight diagonal. On approach from the west, the left (south) side gives you Lake Michigan's shoreline, the Chicago downtown skyline including Willis Tower, and the lakefront grid. The right side faces north toward suburban sprawl with no comparable landmarks. Notable sights include: Lake Michigan shoreline and southern lake expanse, Chicago downtown skyline with Willis Tower and the Loop, O'Hare airport layout visible just before touchdown, Chicago River corridor threading through the grid.

The flight from Ellsworth Afb (RCA) to Chicago Ohare International (ORD) takes Approximately 2 hours 15 minutes to 2 hours 30 minutes.

The flight crosses the Missouri River shortly after departure, then traverses the flat agricultural plains of eastern South Dakota and southwestern Minnesota. The Minnesota River valley is visible near Mankato. The Mississippi River crossing near La Crosse or the Twin Cities area is a notable landmark — wide braided channel with bluffs on both sides. Wisconsin's rolling farmland and lake-dotted terrain follows before the Chicago metro sprawl begins.