Sit on the Left side of the plane for the best views on flights from Cleveland to Chicago. Left side wins at both ends of this short westbound flight. During the brief cruise at altitude over northern Indiana, the left side also faces toward Lake Michigan's southern tip near Gary, Indiana, which becomes faintly visible on clear days. Right side offers little beyond flat agricultural land throughout.

During takeoff from Cleveland Hopkins International (CLE), sit on the Left side for the best views. Cleveland Hopkins typically departs westbound on runway 24L/24R, meaning a left-side seat faces south and southwest during climb-out, giving you a clear view of downtown Cleveland's skyline and the southern shore of Lake Erie. The city grid and the Cuyahoga River valley are visible before the aircraft turns west toward Chicago. Notable sights include: Downtown Cleveland skyline, Lake Erie southern shoreline, Cuyahoga River valley, Cleveland's inner-ring suburbs spreading east-southeast.

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 (runway 10/28 complex) or southeast-northwest, with the approach path crossing over the southern suburbs of Chicago. A left-side seat on approach from the east gives a view of the Chicago skyline to the north and Lake Michigan's southwestern shoreline. The dense suburban grid of Cook County is visible below throughout the descent. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock visible on horizon), Lake Michigan southwestern shoreline, Cook County suburban grid, O'Hare's distinctive multi-runway complex.

The flight from Cleveland Hopkins International (CLE) to Chicago Ohare International (ORD) takes Approximately 45-55 minutes.

The flight crosses northern Ohio and northern Indiana at low cruise altitude, passing over flat agricultural land and small industrial cities including Elkhart and Gary, Indiana. On clear days, the southern tip of Lake Michigan near Gary/Hammond is visible to the left (north) side roughly 15-20 minutes before landing. The terrain is uniformly flat with a dense grid of farm fields, county roads, and small towns throughout.