Sit on the Left side of the plane for the best views on flights from Louisville to Chicago. Left side wins both ends of this flight. The Ohio River and Louisville skyline on departure and Lake Michigan with the Chicago lakefront on arrival are the two highlights, both on the left. The cruise portion over flat Indiana farmland offers little differentiation between sides.

During takeoff from Bowman Fld (LOU), sit on the Left side for the best views. Bowman Field's primary departure heading toward Chicago is roughly northwest. A left-side seat gives you a view back over downtown Louisville and the Ohio River as you climb out, with the river's broad bend clearly visible below. The urban grid of Louisville's downtown and the bridges spanning the Ohio are easily identifiable from low altitude. Notable sights include: Ohio River bend south of downtown Louisville, Louisville downtown skyline, Clark Memorial and Kennedy bridges over the Ohio, Indiana flatlands across the river.

When landing at Chicago Ohare International (ORD), sit on the Left side for the best views. O'Hare's most common arrival paths from the southeast put the left side facing south toward the city. On approach from the south or southeast, the left window gives a clear view of Lake Michigan's southern shoreline, the Chicago lakefront, and the downtown skyline. The lake's blue expanse contrasting with the dense urban grid is one of the most striking aerial views in the Midwest. Notable sights include: Lake Michigan southern shoreline, Chicago downtown skyline and lakefront, Grant Park and Museum Campus from altitude, dense Chicago urban grid stretching west.

The flight from Bowman Fld (LOU) to Chicago Ohare International (ORD) takes Approximately 45-55 minutes.

The flight tracks northwest over central Indiana, crossing flat agricultural land with a patchwork of corn and soybean fields, small towns, and the occasional river drainage. The Kankakee River valley may be faintly visible near the Illinois border. No significant terrain changes — this is the flat interior of the Midwest with elevations barely varying from 600 to 800 feet throughout.