Sit on the Right side of the plane for the best views on flights from Chicago to Louisville. Right-side seats win overall because the takeoff view of Chicago's iconic skyline and Lake Michigan is more visually distinctive than the landing approach. While the Ohio River landing is pleasant, the Chicago departure is a stronger highlight for most passengers.

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 during the initial climb. Midway typically departs runways 31L/31R or 22L/22R; either direction gives right-side views of the downtown core and the lake's western shoreline as you climb southeastward. Notable sights include: Chicago downtown skyline (Willis Tower, Trump Tower visible in clear conditions), Lake Michigan's western shore, Bridgeport neighborhood industrial areas, Des Plaines River valley.

When landing at Bowman Fld (LOU), sit on the Left side for the best views. Left-side seats offer views of the Ohio River and Louisville's downtown during descent into Bowman Field. The approach typically comes from the north or northeast; left-side windows frame the river's distinctive meanders and the city's position along its banks. Notable sights include: Ohio River with its characteristic bends, Louisville downtown skyline, Waterfront Park area, Fort Knox military reservation (visible to the south as large open grounds).

The flight from Chicago Midway International (MDW) to Bowman Fld (LOU) takes Approximately 1 hour 15 minutes.

The flight path crosses central Indiana, passing east of Indianapolis. Notable features include the White River valley, various lakes and reservoirs (including Patoka Lake and Monroe Lake in southern Indiana), and the transition from the flat glaciated plains of northern Indiana to the slightly rolling terrain of the Ohio River basin. The landscape shifts from agricultural grid patterns to increasing forest coverage as you approach Kentucky.