Sit on the Left side of the plane for the best views on flights from Rochester to Chicago. The left side delivers the best views at both ends of this flight — Lake Ontario on departure and the Chicago skyline with Lake Michigan on approach. During cruise the left side also faces generally south, keeping you oriented toward the more populated and geographically interesting southern Great Lakes corridor.

During takeoff from Greater Rochester International (ROC), sit on the Left side for the best views. Rochester typically departs runway 28 heading west, putting Lake Ontario directly off the left (south-facing) side during the initial climb and turn. You get a clear view of the lake's southern shoreline, the city of Rochester spread below, and the Genesee River cutting through downtown toward the lake. Notable sights include: Lake Ontario southern shoreline, Genesee River gorge and downtown Rochester, Rochester's suburban grid extending south, Lake Ontario's open water horizon to the north.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. Flights from Rochester approach O'Hare typically from the east or northeast, and the dominant runway configuration at ORD uses runways oriented roughly east-west (9L/27R, 10/28). On approach from the northeast, the left side faces south toward downtown Chicago, Lake Michigan's shoreline, and the city's iconic skyline. The right side looks north over suburban sprawl with far less visual interest. Notable sights include: Chicago downtown skyline on the southern horizon, Lake Michigan shoreline visible to the southeast, suburban Cook County grid below, O'Hare's massive runway complex coming into view ahead.

The flight from Greater Rochester International (ROC) to Chicago Ohare International (ORD) takes Approximately 1 hour to 1 hour 15 minutes.

The flight tracks roughly west-southwest across upstate New York and then northern Indiana. Visible features at cruise altitude include the flat agricultural plains of northern Indiana, occasional small lakes and river systems including the Kankakee River drainage, and the transition from the Great Lakes lowlands into the Chicago metropolitan area. Lake Erie's eastern end may be briefly visible to the south early in the flight on clear days.