Sit on the Left side of the plane for the best views on flights from Chicago to Louisville. The left seat wins overall because the Chicago departure view — with the full skyline and Lake Michigan shoreline — is more dramatic and visually distinctive than the landing approach. The flight path trends southeast, so the left side also tracks closer to the urban corridor and the Wabash River valley through Indiana during cruise.

During takeoff from Chicago Ohare International (ORD), sit on the Left side for the best views. ORD's most common departures head southeast or east. A left/south-facing seat gives you a clear view back over the Chicago skyline as you climb out, with Lake Michigan's shoreline stretching south toward downtown. The dense urban grid of Chicago's North Side fills the foreground before the lakefront comes into view. Notable sights include: Chicago downtown skyline (Willis Tower, John Hancock), Lake Michigan shoreline, Chicago River corridor, O'Hare's massive runway complex receding behind you.

When landing at Bowman Fld (LOU), sit on the Right side for the best views. Bowman Field sits on the eastern edge of Louisville, and most approaches come in from the north or northwest. A right/west-facing seat gives you a view over downtown Louisville and the Ohio River as you descend, with the river's broad curve clearly visible. The Kentucky Bluegrass countryside fills the approach corridor. Notable sights include: Ohio River and its broad bend at Louisville, downtown Louisville skyline, Churchill Downs (visible as a distinctive oval track), Indiana flatlands across the river.

The flight from Chicago Ohare International (ORD) to Bowman Fld (LOU) takes Approximately 55 to 70 minutes.

The flight crosses the flat agricultural plains of central Indiana, with the Kankakee River visible early in the flight, followed by the broad patchwork of corn and soybean fields around Lafayette and Crawfordsville, Indiana. The Wabash River is a notable dark ribbon crossing the mid-flight corridor. As you approach Kentucky, the terrain begins to roll slightly as the Knobs region north of Louisville comes into view.