Sit on the Right side of the plane for the best views on flights from Chicago to Rochester. Right side wins overall because the takeoff view of Chicago and Lake Michigan is more dramatic and memorable than the landing approach. The landing view is geographically interesting but less visually striking than departing over a major metropolitan area and the Great Lakes shoreline.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats capture the Chicago skyline and Lake Michigan as you climb out westbound. Midway typically departs runways 31L/31R (westbound), so right seats get the best angle on downtown Chicago and the lakefront during initial climb. Notable sights include: Chicago downtown skyline (Willis Tower visible), Lake Michigan shoreline, Chicago's South Side residential grid, Des Plaines River valley.

When landing at Greater Rochester International (ROC), sit on the Left side for the best views. Left seats provide excellent views of the Finger Lakes region and Genesee River valley during approach into Rochester. Typical landing runways are 04/22; if landing northbound on 04, left seats face the lakes and terrain that define the approach corridor. Notable sights include: Genesee River gorge and valley, Finger Lakes (Seneca and Cayuga Lakes visible to the south), Rochester's urban core along the river, surrounding Appalachian plateau terrain.

The flight from Chicago Midway International (MDW) to Greater Rochester International (ROC) takes Approximately 1 hour 45 minutes.

Flight path crosses northern Ohio and southern Lake Erie, then transitions into western New York. Notable features include the southern shore of Lake Erie (visible from altitude), the Cuyahoga River valley near Cleveland, and the transition from the Great Lakes plain into the Appalachian Plateau terrain that characterizes central and western New York. The landscape shifts from relatively flat glaciated terrain to rolling hills as you approach Rochester.