Sit on the Right side of the plane for the best views on flights from Chicago to Detroit. Right-side seats win overall because the takeoff view of Lake Michigan and Chicago's skyline is more visually distinctive than the landing approach. While the Detroit River landing is notable, the Chicago departure offers superior urban and water features.

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 heading northwest, so right windows get the best angle on downtown Chicago's high-rises and the lake's eastern shoreline during the initial climb. Notable sights include: Lake Michigan (immediate eastern boundary), Chicago downtown skyline (south-southwest), Pilsen and Little Village neighborhoods (southwest industrial areas), Des Plaines River valley (north).

When landing at Detroit Metro Wayne Co (DTW), sit on the Left side for the best views. Left-side seats offer views of the Detroit River, Windsor Ontario, and the approach corridor over suburban Detroit. Arriving aircraft typically use runways 3L/3R (heading northeast), so left windows frame the river and Canadian shoreline during descent, plus glimpses of downtown Detroit's skyline to the south. Notable sights include: Detroit River (primary visual feature during approach), Windsor Ontario waterfront (north of river), Lake St. Clair (northeast in distance), Dearborn and Inkster suburbs (south and west).

The flight from Chicago Midway International (MDW) to Detroit Metro Wayne Co (DTW) takes Approximately 1 hour 15 minutes.

The flight path crosses northwestern Indiana and southern Michigan, passing over the southern shore of Lake Michigan (visible from both sides during cruise), the towns of Valparaiso and South Bend area to the south, and the flat agricultural landscape of southern Michigan. The Kalamazoo River valley and scattered lakes of southwestern Michigan appear in the midpoint cruise phase. No major mountain ranges are visible on this route—the terrain is uniformly flat to gently rolling throughout.